The Benefit of Friends

Prologue: Natalie
I guess it was mostly my fault. Maybe if I had not worked so much. Maybe if I had not been so tired. Maybe if I would have been more willing to make love like in the old days. Then maybe all this would not have happened.
My girlfriend, Natalie, and I met in college 7 years ago. At the time I was in a relationship that lasted much longer than it should have. Natalie and I both knew there was an attraction between the two of us, but neither of us acted on it. The attraction was not just physical. She and I had a mental connection that I did not have with my girlfriend at the time.
Although I lived near our college and Natalie returned to her home about an hour and a half away after graduation, we stayed in touch via text messages and cards and letters. When my relationship finally ended, and I was able to pursue other interests, Natalie was the first one I went after. Within five months I was packing my bags and moving into an apartment with Natalie in her town.
At first, our sex life was great. Before I moved up to be with Natalie, we would get together every week or so and rarely left the bed. Once we moved in together, things were mostly the same. Natalie and I would have sex several times a day.
Then things started to change. Like I said, maybe it was my fault. Maybe I became less sexually interested. But I never, ever, expected her to do this.
Natalie’s mother got me job at her office when I moved in with Natalie. Occasionally the job required me to go on overnight trips. I was scheduled to go on one of these trips one month, but an unexpected issue arose at the offsite office, and the trip had to be canceled. I did not tell Natalie, and tried to surprise her by coming home unexpectedly. What I found when I came home is what started this wild and crazy adventure.

I never expected to find her in bed with him. I say “him” because to this day I still do not know what his name is. Frankly, I do not really care either. Sure I was mad at first, super mad. But, damn it, I love her. I have since that first day of college, and I probably always will. That is why, when I finally calmed down, I could not just leave. I knew there was a way for us to work it out. I got another huge surprise when Natalie told me her idea, though. At first I said no, there was no way I was going to go for it. But Natalie insisted that the only way I could ever forgive her, was if I too had sex with someone else.
She said she did not care who. She said she did not care when. She said she did not even want to know when or if I had done it. She said that she would assume we were even, and we could keep our relationship intact. I was blown away.
“Why stop there?” I asked, anger rising in my voice.
“What do you mean?” Natalie answered.
“Why just once? Why don’t you keep fucking him or whoever and I’ll fuck whoever I want and that’s how it’ll be?” I asked. I really did not mean it. It was really just the anger talking.
But when her answer was “Well that might be a good idea,” I did not know what to say.
So here we are. Like I said, it is my fault. Hell it was even my idea. And now I have her blessing to sleep around with other women. Honestly, I never planned on actually doing it, but the more I thought about it, the more I started looking at other girls. And the more I started looking at other girls, the more sexually attracted to them I became.
How do I go about hooking up with someone else though? I was new to this town and did not know anyone other than Natalie’s friends and family, and clearly I could not approach any of them for help. Like I said, I was not even 100% sure I wanted to do anything, but little did I know just how far I would go.

Chapter One: Allison
I was searching the internet one day when I stumbled onto one of those adult dating sites. I had nothing to lose, so I created an account just to see what would happen. A few days went by and I got no action on my profile. I realized it was a long shot anyway.
Natalie told me she was going out with her friends one night. Deep down I assumed she was with him, or some other guy. I did not really know what I was doing, or what I was expecting, but I went to a local bar for some drinks. I knew this was a popular hangout for most of the 20-somethings in town, and thought maybe I would meet someone of my own.
After being there for half an hour I was ready to leave. I was having absolutely no luck with any of the girls in the place. Just then I felt my phone vibrate in my pocket. I pulled it out and saw I had received an e-mail. I opened the message, and saw that it was from a girl who found my profile on the website.
The e-mail said that my profile intrigued her, and she wanted to get to know me. I was not having any fun at the bar, so I went home and fired up my computer. I quickly booted up my e-mail and sent a quick reply to the girl. The girl, who called herself Ally-cat, was obviously still online, because she replied to my e-mail quickly. Over the next couple hours, Ally-cat and I traded e-mails. We seemed to really hit it off and had a good connection.
I had made sure to not post my picture on the site, for fear that one of Natalie’s friends would find it and the situation would be too awkward to explain. Ally-cat had likewise not posted any photos of herself. When I finally felt comfortable enough to trade pictures with her, I asked Ally-cat if I could see what she looked like. Her response surprised me. It was the longest I had waited before receiving a response from her, about 45 minutes. I thought I had scared her off, but when I finally got a response Ally-cat told me I could see what she looked like when I met her in the hotel bar across town the following night.
I was initially surprised. I knew she and I had seemed to hit it off and had a good connection, but I did not expect her to purpose a meeting so quickly, if at all. But the website we met on was designed to find people to hook up with, and I guess that’s really what she wanted. The more I thought about it though, the more excited I became. It was just drinks right? Or was it? I decided to accept and see what might happen.
I went to the agreed upon hotel early the day of the meeting. I had told Natalie I had to go overnight for work and would be home the next day, and got a room at the hotel. I was not sure if I would be sleeping there alone or not, but decided it would be a good idea to have just in case things heated up.
I was supposed to meet Ally-cat in the bar at 9:00. I purchased a single red rose earlier and left it with the bar tender with the instructions to give it to a girl when she came in asking for me. I had explained this to Ally-cat when I accepted her invitation earlier. I sat in a booth toward the back of the bar with a good view of not only the bar, but the front door as well.
Time went by and several girls walked through the door and went toward the bar. A few of them I thought were very attractive, and found myself hoping the bar tender would hand them my rose, but he never did. 9:00 came and went, and still no one was given my rose.
It was about 9:15, and I was just beginning to think Ally-cat would not show when I saw a girl walk into the bar. My heart suddenly began pounding in my chest. I was sure she could probably hear it across the busy bar. It was one of Natalie’s good friends, Allison.
“Oh my god” I said to myself. “She can’t see me here talking to another girl.” I began thinking of a way to sneak out of the bar without her seeing me. Allison looked around the bar for a moment, and then she walked toward the bar. I thought that while she ordered a drink would be my opportunity to sneak out, so I watched her as she went to the bar tender and began talking to him. Suddenly it felt as if my heart exploded.
The bartender handed Allison my flower! I had not put it together till that moment, but obviously Ally-cat was short for Allison. After handing Allison the rose I had left for her, the bartender pointed directly to where I sat. Allison turned and saw me. I was stuck. There was no sneaking out now. Allison froze in place. She had a shocked look upon her face, one that probably matched my own.
I did not know what to do. I did not know what Allison would do. Would we just stare at each other all night? Allison made the choice first though. She began walking toward my table.
As Allison crossed to bar toward me, I allowed my mind to wonder. I had always found Allison attractive. When I first began talking with Natalie again, and we discussed starting a relationship, she told me I would need to meet, and get the approval of, her friends. In a joke among them and me, I was told to “beware the little one”. The “little one” referred to Allison and her height of only about 4’7” tall. Allison was a slightly plump girl with gentle curves that I found not unattractive looking. She had straight blonde hair that came to just below her shoulders, and light blue eyes. She had a cute round face with a slightly upturned nose. She was not what most people would call drop dead gorgeous, and not the most attractive of Natalie’s circle of friends, but she was good looking and I do recall myself checking her out on more than one occasion. Tonight Allison wore a little black dress that came down to just above her knee and showed off her curves very nicely. The dress was held up by two thin straps on each of her shoulders. She was wearing black stockings and high heeled black shoes. Although my heart was pounding intensely and I was scared about what would happen next, I could not help but think how good Allison looked that night.
She weaved her way through the people in the busy bar and came up to where I sat. She sat in the booth across from me. Neither of us knew what to say.
“Umm… hey” I finally said
“Hi” Allison replied, obviously as nervous as I was.
Allison, from what I knew, was in a long term relationship with a guy named Ben. Ben had actually been one of the nicest of the group toward me when I first moved to town; always talking to me and making me feel welcome. But things were not always great between him and Allison. Allison lived with Ben when I first moved, but recently she had decided to move out. She moved back in with her parents, but was still with Ben and stayed with him on the weekends. At least that is what I thought the situation was. Obviously Allison was looking for more than Ben gave her, and that brought her to my table in the hotel bar.
“I guess this was for me?” Allison added, indicating the single rose she held.
“Yeah it is,” I said. “I sure did not expect you to be the one who got it though.”
After seeing someone else join me, a waitress came over to our table. We ordered a couple of drinks. “We’re going to need them,” I thought.
Neither of us still knew just what to say, but I realized we had to talk about this situation. We both knew why we were here, so I decided to not beat around the bush.
“So things aren’t going good with you and Ben?” I asked.
“I don’t know…” Allison answered. “I do think I love him, you know, it’s just he never seems to want to have sex with me, and when we do its way too short and not very good.”
“So you’re cheating on him?” I asked.
At first Allison was taken aback by my accusation. “Well this would have been my first time,” she said, looking down at her drink instead of at me. Then she suddenly looked up at me and added “What about you?! You’re cheating on my friend!”
“Calm down,” I said. “Natalie cheated on me first. This is our way of keeping things fair I guess. I know it sounds crazy, but she is fully aware of this and is ok with it.”
“Oh,” Allison responded. “Doubt she would be ok with it being me though.”
“Well, probably not,” I answered. “But that’s why I tried to find someone I didn’t know online.” Then I added, “What about you? Why would you want to do it with a stranger?”
“I don’t really know,” Allison replied. “I guess I’d rather it be with someone I knew, but I didn’t know how else to go about finding someone to have an affair with” she said mater-of-factly
We both laughed. I could tell we were both very nervous and did not know what to do next.
“What about you?” she asked. “Why would you rather be with a stranger?”
I said, “To be honest I wouldn’t, but I don’t know many people up here yet. I would rather it be with someone I knew actually. Someone I had always thought was very attractive.” I looked Allison up and down.
I could not believe what I had just said. Maybe it was the alcohol, maybe it was that I had intended to have sex that night, or maybe it was that deep down I had always had some feelings for Allison. Allison looked back at her drink and noticeably blushed. I knew that I was playing with fire and needed to get out of there before I did or said something that would burn me.
“Well look,” I said “I know this isn’t what either of us wanted or expected. I guess we just go our separate ways and forget this ever happened.” I started to get up from the table. I reached into my pocket to pull out money to pay for our drinks and happened to pull the pair of hotel door keys out as well.
Again I do not know what I was thinking, but what I said and did next I think took both of us by surprise. I laid one of the keys down on the table and slid it toward Allison.
“I’ll be up there alone all night,” I said. “If you want to join me, you’re more than welcome”
Allison looked at me, shocked. She picked the key up and studied it like it was a rare relic.
“Room 217,” I said, than turned and walked away without another word.
.
I rode the elevator up to the second floor and walked to my room. I used my one remaining door key to gain access to the room and closed the door behind me. I stood there for several moments with my back against the door, more than once hitting my head backward against the hard wood of the door.
What the hell was I thinking? Any chance I had of Allison not telling Natalie about this encounter surely flew out the window the moment I invited her to my hotel room.
“Unless she actually came up here,” I said aloud, knowing there was no one there to hear me. The idea that she might actually come up to the room to be with me was such an exciting one that I immediately moved away from the door, imagining I might be preventing her from opening it.
Not surprisingly, though, the door did not open. I sat on the bed and turned the television on. I flipped through the channels randomly, paying more attention to the un-opening door than the t.v. screen. After what felt like hours, but was really only about 45 minutes I decided she was not coming. I knew it was a hopeless dream anyway.
“She did look very good in the little black dress,” I thought to myself, but I knew it was foolish. I got up and went to the bathroom to take a cold shower. I turned the television set off as I walked by.
I let the cool water wash over my heated body. It felt good. I was racking my mind trying to think of ways to tell Natalie about me inviting one of her best friends to my hotel room. I had a license to cheat, sure, but with a friend? I knew that was another thing entirely.
Finally I realized I had spent enough time trying to wash my troubles away and turned the shower off. I stepped out of the shower and grabbed a towel from the rack above the toilet. I began to dry my hair, listening to the movie playing on the television in the next room.
It was not until I heard the channel change that I realized I had turned the set off before going for my shower.
“Great,” I thought “on top of everything, my room is haunted.” I wrapped the towel around my naked waist and opened the bathroom door. I walked into the hotel room and was shocked by what I saw.
Allison was sitting on the bed. She looked at me as I entered the room. Seeing my lack of attire, Allison looked me up and down, taking in the sight.
“I didn’t think you were coming,” I said as I began walking toward the bed.
“Well,” she responded “I wasn’t going to, but the more I thought about it I realized you were right. I would rather do this with someone I knew.”
“Oh, is that so?” I asked.
“Yeah,” Allison answered “someone I know won’t hurt me or anything. And someone I know can give me what I need.”
I was not sure what she meant by that last comment. “And I can give you what you need?” I asked.
“Well, Natalie did tell me about your um… gifts” Allison said.
I was a little shocked that Natalie had been spreading the word about my size. But girls will talk I suppose. I said to Allison “Oh she did, did she? Well how do you know she was telling the truth?” At this point I was standing next to the bed. Allison turned so she was sitting on the edge of the bed directly in front of me.
“Let’s find out” She said. Allison reached up and undid the towel from around my waist and let it fall to the floor.
As I stood nude in front of Allison, she ran her hands up my legs. Her hands began to near my crotch. I was surprised we had reached this moment. This evening had been a roller coaster of emotions, and deep down I still felt a sense of trepidation about committing the act with someone so close to my girlfriend. Allison’s hands reached my penis, though, and I pushed all the fears I might have had from my mind and enjoyed the moment and the sensations I was receiving.
The fingers on Allison’s right hand began to encircle my shaft while her left hand cupped my balls and began to gently roll them. Allison did not take her eyes from my crotch as she began pumping on my shaft with her hand. I grew hard in her hand, the feeling of her hands on my privates very intense. Slowly Allison raised her gaze to me, and our eyes met. She had a look of fiery passion in her eyes.
Allison’s eyes fell back to my now hard penis as she continued to jack it off. Then she leaned forward and her pumping motion slowed. Allison held my shaft upward and leaned in to lick the underside of my penis from the base just above my balls all the way to the tip. Her tongue swirled around the head, before going back down the side to the base again. Allison’s licking felt wonderful on my hot shaft. After a couple more trips up and down my shaft, Allison continued her pumping of my penis, aided now by her saliva which coated my shaft.
Then, to add to the pleasure Allison was giving me, she leaned forward once again, and this time took the head of my penis into her mouth. She began to suck on the tip of my penis while her hand continued to jack me off. I moved my hand to the back of her head and applied a small amount of pressure. I started to moan loudly. Allison could not take a large amount of my thick penis into her mouth, so I let her suck on the head as her hand began to twist around my shaft as she pumped. I was amazed that, although she could not take very much into her mouth, she made up for it with her hands, and it felt incredible.
Although I was enjoying this very much, there were other things I wanted to with Allison before the night was through, and time was already not on our sides. I took my hand off the back of Allison’s head, and took her hands. I pulled her to her feet and kissed her mouth. Our tongues met and danced around one another, moving back and forth from her mouth to mine. My hands began to explore her body, starting first at her soft backside. I squeezed her amble butt cheeks with both of my hands as we kissed. Then I moved my hands up her body. I lightly grazed over her breasts, at which point she let out a light moan, but they were not my target, not yet. My hands continued higher till I reached her shoulders. My fingers wrapped around the straps of her dress and lightly fell to the sides, pulling the thin straps away with them. I released my hold on the straps and pulled back from her, allowing Allison’s dress to fall to the floor around her feet.
I saw that Allison wore a pair of black lacy panties and that her stockings came up only to her thighs. Her panties were cut very skimpy and looked amazing on her. I now saw that hidden behind her clothing was an incredibly sexy body. The gentle curves of her plump body were very exciting, and I could not wait to touch, and taste it. I had Allison lie back on the bed as I climbed into the bed next to her. As great as she looked in her panties, it was what was beneath them that I really wanted. I lightly slid my fingers under the waist band on either side and pulled them down and off her stockinged feet.
As I lay next to Allison on the bed I could tell her heart was beating very fast, as was mine. Her breathing had become very quick and heavy, and her skin was turning a bright red color. I could tell she was nervous about what we were doing, and what we might do next, and I did my best to put her mind at ease.
“We can stop at any point you want,” I said.
“Please don’t stop,” Allison replied, looking into my eyes. I could tell that although she was nervous she wanted this as much as I did.
I leaned in and kissed Allison’s cheek, then continued kissing, moving down her neck. As I kissed and lightly nibbled on her neck, goose bumps formed all over Allison’s skin even in the warm air of the hotel room. I could tell I was having a glorious effect on her. My hands found Allison’s breasts as I continued to kiss her neck, and I began to squeeze and rub them. She had round breasts that were heavy in my hands. They were not overly large, but the dark nipple that was on the tip of each one was big and thick. I took those nipples and pinched them between my fingers and thumbs. At this new sensation, Allison let out a sweet sounding moan that was music to my ears. I continued traveling down Allison’s body with my mouth and found one of the breasts I had been toying with.

I took Allison’s breast into my mouth, sucking on her nipple. While her breast was in my mouth I began flicking her large nipple with my tongue. I pulled her breast from my mouth and continued to lick her nipple, swirling it around with my tongue. I moved my other hand lower down Allison’s body and found the warm mound between her legs. Allison kept the hair above her vagina trimmed very short and my fingers slid through the small patch on their way to her wet lips. My fingers slowly lid up and down the slit between her legs and I continued to lick and suck on her breasts. Allison was moaning very loudly at this point
As my fingers began to part Allison’s lips and could feel the moisture beneath, I tore myself away from her chest and continued down her body. I kissed and licked her smooth skin moving over her belly and toward her crotch. I moved to the side as I neared her pussy and kissed her thighs as my fingers lightly gained entry to her vagina. I slid my fingers in and out a couple of times while I teased her with my tongue, getting very near her crotch without licking it. Finally I withdrew my slick fingers and replaced them with my mouth.
I first kissed her pussy lips, and then I licked her from the tip of her lips all the way down, then back again. Using my fingers I pulled her lips apart slightly and slid my tongue into her warm vaginal canal. I began to slide it in and out, making love to Allison with my tongue. Then I pulled my tongue out and found the thick clit at the top of Allison’s pussy. I flicked it with my tongue then slid my fingers back into her vagina as I licked and sucked on her clit.
During this whole time Allison was moaning very loudly. I was afraid someone in the room next to ours might be able to hear, but I did not care. I continued giving oral pleasure to Allison for several minutes, delighting in the sweet taste of her body, until her moaning reached a crescendo. I could tell Allison was cumming, and I could feel her body tense around my fingers.
After bringing Allison off, I wanted more. I stood up from the bed and look at what a stunning sight Allison was lying on the bed naked, legs spread, a look of pure desire on her face. We both knew what was going to happen next, and we were both happy it was going to happen. I grabbed a condom from my overnight bag and quickly put it on. I climbed back into the bed, between Allison’s legs and positioned the head of my cock at the entrance to Allison’s pussy. I looked deep into her eyes as I pushed. Allison let out another loud moan as my penis entered her. I push it in as far as I could and waited for her to get used to the increased size of my member. After a few moments though, the feeling of being inside Allison’s tight pussy was too much, and I began to make love to her with long, forceful thrusts. I knew Allison wanted someone to give her a ride her boyfriend never could, and I intended to give it to her.
Allison began to respond to every thrust I gave her by pushing back against me and letting out a little scream with each thrust. These screams continued to increase in volume as well as length as my thrusting continued. The thrill of making love to Allison, along with her passion was too much for me to handle, though. As Allison’s noises reached a level that I was sure not only the people next door, but the entire floor could hear, I gave one final thrust as deep as I could and let out a loud moan of my own as I exploded with a massive orgasm. Allison, too, climaxed as my body feel upon hers.
We laid there for several minutes, naked, wrapped in each other’s bodies. Soon I had regained control of my body and pulled myself to my feet. Allison and I cleaned ourselves off and got back into the bed. We feel asleep, still naked, in each other’s arms.
The next morning, as the sun was coming up and shining through the window of the hotel room, I woke up to the sound of Allison moving about in the room. I look up to see her pulling her dress up, and hiding her naked body. She noticed my movements and came over to me. She leaned down and we kissed like lovers once again.
“Last night was…” I began.
“Last night never happened” Allison interrupted.
“Okay,” I replied, “but it was still great.”
“Yes it was” Allison replied, gliding her hands over my naked body.
“So do you think it will ‘never happen’ again sometime?” I asked.
“There is a very good chance of that” Allison replied, moving toward the hotel room door. As she reached to door, and was just about to leave me, she turned back and added “And Natalie wasn’t lying.” Then she was gone.
I rolled back over in the big empty bed. I could not believe what I had just done. I knew, however, that Allison would not tell my girlfriend anything about it. I was safe, for now.
CHAPTER 2: Shayna
It had been a couple weeks since my night with Allison. Natalie and I were doing surprisingly well. I assumed she was still having sex with other guys. And I’m sure she assumed I was having sex with other girls. She never confronted me about Allison, so I gratefully assumed she did not know. In fact, Natalie and I seemed to be having more sex than usual and had become closer emotionally. I did not know when, or if, I would have sex with someone else, but after the great fun I had with Allison, I was not against the idea.
One evening I was sitting in my apartment, watching ESPN on the television. I was bored and slightly frustrated. Natalie had said she was going shopping with her mother and would not be home until late, but in the back of my mind I wondered if she was really with some other guy. I wasn’t mad about it; I gave her my blessing to do it if she wanted. I was actually mad at myself. Here I was, sitting at home, alone, when I could be out finding a girl to have some fun with. If my girlfriend could do it, why shouldn’t I?
Just as I was thinking about maybe going to a bar to find someone my phone rang. I checked the caller ID and saw that it was Shayna. I thought it was odd because Shayna did not typically call me. Shayna and I have been friends for as long as Natalie and I. Shayna and Natalie had been best friends since they were little, and when Natalie picked our school for college, Shayna went with her. So I met Shayna at the same time as Natalie. Shayna and I did not have the same emotional attraction as Natalie and I had, but we still became very close friends. To this day, out of all of Natalie’s friends, Shayna is by far her best friend.
I answered the phone and Shayna sounded a bit panicked. It took me a few seconds to calm her down enough to tell me what was wrong. Apparently her washing machine had sprung a leak and was spraying water across her basement.
“Can you please come over and help me…. I don’t know what to do.” she said. It sounded like she was close to tears.
I was quickly in my car and making the short drive to Shayna’s house. Shayna lived in a house owned by her boyfriend. He was in the National Guard, and had been overseas in Iraq for several months. While he was away, there was a little joke amongst Shayna, Natalie and I that I was Shayna’s “other” boyfriend. It was a cute way of saying that when Shayna needed something done I would be there to help her, the way her boyfriend would have been if he was there.
When I arrived at Shayna’s place I quickly turned the water valve off and stopped the spray. I inspected the connections and noticed that the hose running to the washing machine had a hole in it. I knew it would require replacing. I told Shayna to start cleaning the water up while I ran to the store and bought a replacement.
I was quickly back at Shayna’s house with the replacement part. Shayna had changed out of her wet clothing and was now wearing a simple t-shirt and jeans. Soon I had replaced the part and the washing machine was fixed and working as good as new.
“Thank you so much” Shayna said to me as I turned the washing machine back off after testing it.
“You’re welcome,” I said. “I am your ‘other’ boyfriend after all. It’s part of my job. I’m here to help you with anything you need” I added with a smile.
At this, Shayna slightly turned away and mummbled under her breath. “Not everything.” She did not think I heard her, but I did.
“Are you sure there is nothing else I can help you with while I am here?” I asked.
“No, I’m sure” she answered, then added “I can get it myself.”
I really was just joking. I seriously did not mean it to be anything more than a joke and meant nothing more than to put a smile on her face, but I said to Shayna “Yeah, but it’s more fun with two people.”
We both shared a laugh, but then our eyes met and I noticed something in Shayna’s look. “Are you serious?” she asked.
I was shocked. I was just joking. I really did not mean anything by it, but on the other hand…
Shayna was a very attractive girl. She was tall, about 5’5″ and most of that height was from her slender long legs. She was thin and had short red hair. She had pale, fine skin and an attractive, bright face. She had very small, but perky breasts. To say Shayna was not attractive would be untrue. I cannot say that I never thought about her in sexual terms, especially back in college. But Shayna was Natalie’s best friend. Not just one of her group like Allison, but her best friend. Could I really do anything with her?
Then I thought about how many guys Natalie had probably been with. I thought about how she was probably with one of them right at that moment, and I decided to go for it. I stepped toward Shayna. I was now standing directly in front of her and I reached out and began touching her arm, rubbing it up and down, as we looked into each other’s eyes.
“Yes,” I said, changing the tone of my voice from one of a playful kidding tone to one of a serious straightforwardness. “I told you, I will help you with whatever you need.”
“It’s just… I haven’t had anyone touch me…” as she said this, I felt goose bumps form below my hand on Shayna’s arm, “I haven’t been able to kiss anyone in so long.”
I stepped even closer to Shayna, our bodies were now pressing against each other. “Anything, Shayna, anything you might need” I said. I got us this far, but I was going to make Shayna make the first real move.
“Anything?” Shayna asked.
“Anything” I said
Shayna leaned forward and our lips met. We began to kiss. We kissed softly a few times, but then our mouths opened. Our tongues began to playfully swirl around each other as we made out standing on the wet floor of her basement.
I began to move my hand from her arm to other parts of her body. First to her back, then around to her front. I soon was rubbing Shayna’s small perky mounds.
Our kiss ended and Shayna and I leaned back away from each other. Shayna looked down at my hands which were still upon her chest. I suddenly had a feeling that I had gone too far. I pulled my hands away.
“Sorry,” I said, “I just thought that…”
Shayna took my hands and placed them back on her breasts. “Please,” she said “don’t stop.” Her hands were shaking.
I continued to rub her small mounds, leaning down and kissing Shayna’s neck. She began to moan.
“Let’s go upstairs” she said. Shayna led me to her bedroom and lied down on her back on the bed. I crawled beside her, lying on my side next to her. I continued rubbing her chest while kissing her neck. Shayna then had me stop and removed her t-shirt. I reached behind her and unhooked Shayna’s bra which she likewise removed. I could now see more of Shayna’s body than I ever expected to see. Her light, pale skin was extremely sexy. She was breathing heavy, and as I looked at her the skin on her chest became a bright red. She was obviously nervous about what we were about to do, but I could tell she was just as excited as I was.
I began to rub Shayna’s bare breasts, lightly pinching her bright pink nipples. I continued kissing her neck, but quickly made my way down and began kissing and lightly nibbling on Shayna’s breasts and nipples. Although they were quite small, Shayna had fantastic breasts. They were soft and delicious to suck on, and by the way Shayna was moaning I could tell she was enjoying it. But I was not about to stop there. My hands found the button on Shayna’s jeans, and it was quickly undone. I waited a few moments to see if Shayna would protest before pulling the zipper on her jeans down. I then leaned up and began to pull Shayna’s pants down. I stopped to ask her if it was ok, and her only answer was nodding her head, never looking away from my hands on her pants. I continued pulling her pants off.
I took Shayna’s jeans off her feet and tossed them to the floor. Shayna pulled her panties off, and she now lay nude on the bed. I looked upon Shayna’s naked body. Her long legs looked amazing bare, and as my eyes fell between her legs I saw that Shayna had trimmed her pubic hair to a neat line leading down to her tight lips.
“Will you please… just… lick me?” Shayna asked spreading her legs. As her legs spread apart I noticed how moist the area between them was. I knew it had been a long time since Shayna was able to be with a man, and I now saw just how much she wanted it.
“I told you, anything you want” I answered.
I crawled between Shayna’s legs, kissing her inner thighs, moving upward. Shayna began moaning loudly as I reached her neatly trimmed vagina. I begin licking her slit up and down. Using my fingers I spread her lips apart slightly, giving a better view of her private area as well as better access for my hungry tongue. I could now see that she was extremely wet, and I saw that her clitoris was swollen and hard, begging to be toyed with. Shayna began panting and moving about a great deal as I licked her clit and pushed my tongue into her hole. I felt Shayna begin to quiver as she had an orgasm. She then pulled my head into her, making sure I did not stop. I continued licking until Shayna came at least one more time, if not twice, before finally allowing me to lean up.
I was not sure if Shayna wanted more or not, but I got my answer quickly as she undid my pants. As I pulled them off Shayna got a condom from her bedside table. I put the condom on my hard penis and leaned toward Shayna. She guided me into her, and before long I was fully inside her.
I worked myself in and out of Shayna as she mimicked my movements from underneath me. She was very loud. We rocked this way for a long while. I was happy to help out my friend in her time of need, but I was enjoying this myself just as much. It was obvious she had wanted it for a very long time, but that was not all she wanted. She had me stop and pull out of her.
“Now roll over” she commanded. I rolled onto my back, my dick standing straight up into the air. Shayna climbed on top of me and lowered herself onto my penis. After sliding all the way down onto me, Shayna began riding up and down on me. Shayna was thin and light and I grabbed her hips and helped lift her up and down on me, forcing more of myself into her with each thrust.
Shayna’a moaning and panting reached an almost scream like level as I felt her clench down on me and slam down one final time as she had a final large orgasm. I, too, came, exploding in the condom.
Shayna and I lied together for several minutes after we had made love. After some silence she rolled to me and said “Thank you for being there for me, for being such a great friend or ‘other’ boyfriend I should say.”
“No need to thank me,” I said. “I told you, I’m here for anything you need.
I finally got dressed and headed home. Natalie still was not home when I got there.
“I bet she wasn’t having as much fun as me,” I thought to myself.
She finally returned home a little while later, with surprisingly few shopping bags. We kissed and cuddled as we went to bed, having no mention of either of us sleeping around.

Interlude: Cook out
Two weeks after my time with Shayna Natalie’s parents were going on a vacation. Natalie and I agreed to stay at their house while they were gone to care for their dogs. Natalie’s parents had a large patio and backyard area at their house, and we decided to have a cook out for the group. I was excited, but also a bit nervous about the cook out, because it would be the first time I saw Allison or Shayna since I slept with them.
Shayna was the first to arrive. Natalie was busy running in and out of the house, getting last minute things ready for the cook out. Shayna came to the back yard where I was warming up the grill.
“I just want to thank you again” she said to me, “and also say that I’m sorry.”
“Sorry? Sorry for what?” I asked.
“I’m sorry for putting you in that position. For making you cheat on Natalie” she responded.
“You didn’t make me do anything” I said. “I might not have wanted it quite as much as you, but I wanted it, and I could have stopped you if I didn’t want to do it.”
“Well I don’t know about that” Shayna said. “I might have just tied you up and raped you if you would have resisted. I needed it, badly”
“Well I’m glad it didn’t come to that” I said. “Like I keep saying, I’m your ‘other’ boyfriend. I’m there for you for whatever, and I will always be there.” I said this last part with a wink and a smile. Shayna knew exactly what I ment.
“Um.. thanks,” she said, “but I think I’m going to be ok now.”
“Oh” was all I could say. Had she not enjoyed it? Was it not as good for her as it was for me?
“No no” she said, “it’s not that. It was great, you were great. It’s just I really don’t like cheating on my boyfriend. It was just one time. I needed it to clear my head. Now I’m clear and can make it till he comes home.”
“I totally understand,” I said. “Just glad I could be there.” So it was clear that my time with Shayna would just be a onetime thing, but that still left Allison.
The rest of the girls arrived with their significant others. When Allison came in with her boyfriend we greeted each other and hugged like we typically did. Things seemed normal, as if nothing had happened between the two of us.
Allison had brought a watermelon with her for us to have. As we were all sitting around, having a great time, she decided to go into the house to cut some of the melon for us all. As she went into the empty house, I thought it might be the perfect opportunity to have an alone moment with her. I excused myself under the pretense of going to get a trash bag to start cleaning up.
Allison was at the kitchen counter, trying to cut through the thick skin of the watermelon. I quietly walked up behind her. I am not sure whether she knew I was there or not. As I came up behind her I put my arms around her, putting my hands on hers.
“Can I help with that?” I asked.
“Sure,” Allison said, handing me the knife and stepping to the side. I cut through the watermelon, slicing it into pieces. Allison turned toward the cupboard to get bowls, but the bowls were on a shelf just out of her reach. I again came up behind her and reached over her this time to get the bowls. As I did so, I pressed my body against her, rubbing my crotch on her butt.
Allison turned around, still with my body pressed against hers. She looked up into my eyes, and her hands slipped between us, rubbing my semi-hard penis. “Can I help with this?” she asked, mimicking my statement.
“I’m not sure if now is the best time” I said, sad that there were so many other people around.
“I know,” she said, “but soon.”
I let out a low moan as she again rubbed my dick. I could not wait for another time with Allison.
Suddenly the back door opened and Rachel, another of Natalie’s friends, walked into the house. “Need some help carrying the watermelon?” she asked.
Allison and I quickly turned away from each other. I did not think that Rachel saw anything. I hoped Rachel did not see anything. I was sure she did not, but as I grabbed a trash bag and walked past her to go out the door I noticed something in the look on Rachel’s face.
As the day wore on and turned into evening the party was still going on. I was cleaning the grill after spending the day cooking burgers and hotdogs on it. I looked over and saw Allison and Rachel talking privately. As they talked I kept getting the feeling that they were looking at me. I was almost positive I saw Rachel look me up and down at one point, but I knew I had to be seeing things. It had to have been the setting sun playing off the fumes from the grill… right?

Chapter Three: Rachel
Only a few days after the cook out at Natalie’s parent’s house our job house sitting was over and we were back at our apartment. It was a Saturday afternoon, and Natalie had to work the closing shift at her store. I was sitting at home, planning on going out to do some yard work when Natalie sent me a text message. She told me that Rachel would be dropping off some candles for her at some point that day. Rachel sold candles as a way to earn extra money, and Natalie had agreed to buy some. A few minutes later Rachel called me to make sure I would be home. I told her I would, and she said she would be right over.
Out of all of Natalie’s close circle of friends, Rachel was by far the most attractive. She was about 5’6” tall with medium brown hair. She had a curvaceous body and nice tan skin. Her best feature, though, was her breasts. Her breasts were very large and round. I enjoyed spending time with her with Natalie just so I could check her out.
Within minutes Rachel was knocking at my front door. I answered it and let her in. She dropped off a bag containing several boxes of tea light candles. Rachel was wearing a long orange dress that tied around her neck showing off her bare back and arms. I could not help but admire at how sexy she looked, but suddenly snapped myself back to reality. Rachel was married and although I had recently been with two of Natalie’s friends, sleeping with a third was out of the question… or so I thought.
Rachel was heading toward the door to leave when she suddenly turned back toward me. She had a serious look on her face, and looked rather nervous.
“Can I talk to you about something?” She asked me.
“Sure” I said. I motion toward the couch and take a seat in my chair across the room. I had no idea where this was going. Had Allison told her and she was going to confront me about it? “What’s up?” I asked.
“Well,” she began, “you know that Sam and I are trying to have a baby, right?” I was totally taken aback. That was definitely not where I thought this conversation was going to go. Rachel had been married to Sam for longer than I knew them. Recently I had heard that they were trying, unsuccessfully, to become pregnant. I knew they had had several appointments to doctors to try to find out what was preventing them from conceiving, but I did not know what, if anything, they found out.
“Yeees” I said, obviously confused as to why she was bringing it up now.
“Well you see, the problem is with Sam. The doctor said something about low sperm count or something like that. He said that it is unlikely that he could ever make me pregnant.” Rachel said, finding it hard to make eye contact with me. Then she continued, “Unlikely, but not impossible. The only thing I want is to be a mother, and I was just thinking that if… um… someone else…” And she trailed off.
“If someone else did it, Sam would never know.” I finished for her.
“Right!” she said, looking into my eyes, noticeably excited. “But it has to be someone who looks a lot like him, same hair color and all that stuff.”
I always did think Sam and I looked a lot alike, but is this really what she meant? “Wait,” I said, “you want me too… I mean, you want to… with me?”
“Well you did with Allison.” Rachel said.
My jaw literally dropped. “She… she told you?” I asked.
“Yes, well after I saw you and her in the kitchen at Natalie’s cook out she kinda had to tell me. But don’t worry; I won’t say anything to Natalie.” Then Rachel stood up and stared walking toward me. I was frozen; I didn’t really know what to do. Rachel continued, “Sam and I had sex last night, so the timing won’t be an issue at all” she said as she knelt in front of me. She began running her hands up my calves, then over my knees, then her hands began to travel up the legs of gym shorts.
“I’ll make it worth your while,” she said as her left hand reached my shaft and her right cupped my balls.
“Rachel, Rachel, stop,” I told her. I bent down and tried to pull her hands from my shorts. What was I doing? I seriously couldn’t do this… could I?
“But, I just…” Rachel began stammering.
“Wouldn’t that be easier if you took my shorts off?” I asked.
Rachel got a big wide smile on her face. She almost yelped she was so excited. She reached up and pulled my shorts and boxers off. I was already semi hard, but as Rachel’s hands again found my package and her lips began kissing the tip of my penis I grew fully erect. As soon as I was fully hard, Rachel opened her mouth and my entire penis disappeared. I could not believe that she took my full length into her mouth and down her throat. Rachel began to suck, sliding my rod in and out of her mouth. It felt amazing as she played with my sack as she gave me the best blowjob I had ever had.
“Wow Rachel,” I said, “that feels incredible, but unless you want to waste my stuff before we can use it you had better stop.” Rachel gave me one last long suck and pulled my penis out of her mouth. She stood up and reached behind her neck. She untied her dress and it fell to the floor. She was not wearing any underwear, and Rachel now stood in front of me totally naked. I assumed that she had planned this all along, and thought underwear would only get in the way. I was in awe at how incredibly sexy Rachel looked naked. Her breasts were even more amazing than I dreamed of looking at them with clothes on. Her tan body was fantastic; I could not wait to touch her.
I stood up too and kissed Rachel. We immediately began making out, our tongues darting in and out of each other’s mouths. My hands ran up Rachel’s body and began to squeeze her large breasts. They felt wonderful. My super hard penis was pushing against Rachel’s crotch.
I took Rachel’s hand and led her to the bedroom. I had her lay back on the bed. I got on the bed next to her and returned to playing with her breasts. I sucked each of her large brown nipples, playing with them with my tongue. Rachel was moaning and running her hands through my hair. I began to suck on Rachel’s large breasts as my hands were running up and down her body. I began rubbing her inner thighs, getting higher and higher. My fingers found her moist opening and began to play. I slid my fingers up and down the length of her slit then began to flick, pinch, and rub her enlarged clitoris. Rachel continued moaning, but moaned even louder as my fingers slid inside her hole.
I was fingering Rachel’s vagina as I licked and sucked on her breasts. Rachel was very wet, and I could tell she was ready. I crawled between her legs and positioned my member at the entrance to her warm, wet hole. I looked into her eyes as she looked into mine and pressed into her. Rachel moaned as I went in. I was happy that although this encounter was more about giving her a baby than about sexual pleasure, I was glad she was enjoying it as much as I did.
I began to slide in and out of Rachel, the muscles of her vagina squeezing me, almost trying to suck the baby making juice out of me. Rachel wrapped her legs around me pulling me into her with each thrust.
“Please cum for me” Rachel began to say into me ear. “Please squirt your stuff into me and make a baby for me. Please baby, please cum inside me.”
Her dirty talk was more than I could handle. I gave a couple more strong thrusts into Rachel and exploded as I shot my load deep into her womb. At the same time I felt Rachel clench down, obviously orgasming herself.
After a few moments, I slowly pulled myself out of Rachel’s vagina. I rolled to her side and lay next to her. I looked over her body as she laid there breathless. I saw that my cum had filled her hole, and some was dripping out down toward her butt.
Rachel must have been able to feel it leaking out because she reached down and scooped some of it up with her finger. I was shocked when as I watched Rachel put her finger into her mouth and sucking my cum off.
Rachel must have seen my odd look. She smiled at me and said, “Like you said, don’t want to waste any.”
After Rachel and I both got dressed she went to leave. We had a passionate kiss at the door before she exited. “Thanks again,” she said. “I sure hope it worked.”
“Me too,” I said.

Chapter Four: Allison Revisited
A couple of days after my experience with Rachel I was sitting at home with Natalie. Things between the two of us were still going very well. I was happy that not only was I getting to experience sexual relations with several great girls, but I also had a wonderful relationship at home.
Natalie was flipping through channels on the television, watching shows that I had no interest in watching. Suddenly my cell phone beeped. It was the tone indicating I had a text message. I pulled the phone from my pocket and noticed I had received a message from Allison. I thought it was odd, but it also got my excited. I opened the message and saw that it was a picture message. It took a few moments to download and open the message, but when it did I almost called out in surprise.
The image was one of Allison, taken in a mirror. She was completely naked, looking amazing. A caption on the picture read “Cum get me” I typed a quick reply to Allison. “Now?” I asked.
“NOW!” Allison quickly responded.
Natalie asked me to whom I was talking. I quickly made up a story about a friend of mine inviting me to go see a movie. I got up and gave her a kiss and told her I would be back later. I hopped into my car and sped to Allison’s place. She had been staying at Brad’s more and more lately. I assumed things between them were getting better. While I was happy for them, I was also a bit sad. I assumed that each step Allison and Brad took closer together was a step farther from Allison and I ever hooking up again. Based on the picture and texts I got from her, I was obviously wrong.
I pulled up in front of Allison and Brad’s house and noticed his truck was nowhere to be seen. It was early afternoon and I knew he typically worked late. I practically ran up to the front door and knocked. The door quickly opened and I was pulled inside.
Allison pushed my back against the door and began kissing me. She was still nude, and I ran my hands over her lovely body. I squeezed her ample butt as we made out.
When Allison finally broke our kiss she pulled back and looked into my eyes. She was breathing heavy. “Are you happy to see me?” I asked.
“Yes.” Allison answered. “Fuck me like you did that night” she said, and then added “I need it.”
I let her take my hand and lead me into the bed room. When we were next to the bed Allison had me turn around and face her, my back to the bed. She pulled my shirt over my head and then undid my pants as we kissed. My pants fell to the floor and I stepped out of them As soon as I was naked Allison pushed me backward onto the bed.
I fell onto my back and as I lay there Allison attacked. She began licking and kissing my dick. Her hands were rubbing and squeezing and stroking while she sucked as much of me into her as she could. It was very different than the feelings Rachel had given me not to long ago, but it still felt incredible. I had gotten very hard, but as soon I was fully erect Allison stopped sucking. She must have been very horny, because she could not wait to have some action of her own.
Allison rolled on to her back and spread her legs. She gave me a ‘come get me’ look and I crawled toward her. I kissed my way up legs, then her thighs, and finally I began to devour her vagina. She was incredibly wet and tasted amazing. I started by sticking my tongue in and out of her hole. She felt very hot inside. Her clit was very inflamed and sticking out. I took my tongue from her soaking hole and began to flick her clit with it. Allison was moaning and gasping and thrashing around on the bed. Allison seemed to be enjoying it a great deal, but had me stop.
“I want you to fuck me” she purred.
I had come prepared and went to get a condom from my pants pocket. When I had retrieved it and put it on I turned back to the bed. I was surprised by what I saw. Allison was on the bed on her hands and knees; her round butt was sticking straight toward me. She looked back at me with a sly smile and wiggled her ass. I got behind her on my knees and slid my throbbing hot penis into her from behind her. I grabbed onto Allison’s hips and began pulling her back toward me as I thrust into her. Allison began moaning and panting more with each thrust into her. I gave her great butt a light little spank as I continued to make love to her doggy style.
It was not long until Allison began getting very loud. I knew she was close to cumming. I kept thrusting, getting harder and deeper with each pass. Soon Allison began to scream and bite down on her pillow as she had a massive orgasm. I did not stop. I kept pounding for a few more moments until I was ready to cum. Allison had not yet come down from her high and came again as I collapsed on top of her with my own orgasm.
Allison and I lay on the bed tangled in each other’s bodies panting and sweaty for several minutes. After a short time I became aware of Allison’s hand very near my crotch. Her fingers began to move, and she started to touch my now soft penis. She started running her fingers up and down the length of my dick. Before I knew what was happening I started to become hard again, and soon Allison was jacking me off. Without so much as a word we repositioned ourselves and I was again making love to Allison, this time in missionary position. I looked into Allison’s eyes as I moved myself in and out of her still very wet pussy. She looked up at me and we started to kiss. We did not do it hard or fast like we had a few minutes ago. This time we went slowly and I made sure that Allison felt every inch of my member as I pulled and pushed it in and out of her.
Allison and I both lasted much longer this time. We took our times and slowly brought each other off to another amazing orgasm. After we had both cum Allison and I continued to kiss passionately as I grew soft inside her.
A few minutes later we were both dressed and I was getting ready to leave. I knew I needed to get home before I had been gone for too long and Natalie would think anything was amiss. As I was going toward to door Allison spun me around and kissed me.
“Can we do it again sometime?” she asked.
“As long as you don’t keep telling people about us” I replied jokingly.
“Oh,” she said. “Did Rachel say something to you about it?” she asked.
“You can say that” I answered.
“Wait,” Allison said with a bit of surprise, “did you and her…”
“Possibly…” I said.
“Wow, you sure are making the rounds through Natalie’s friends aren’t you?” Allison said laughing.
I thought about my time with Shayna. If only Allison knew how I really was making rounds I thought.
Allison and I kissed again before I left. She told me I would probably be hearing from her soon.
“But you can also contact me if you want some” she added.
I went back to my apartment totally satisfied and hoping that Allison and I could get together again soon.

Chapter 5: Rachel and Dana
After my second time with Allison almost a month passed. During this time the only person I had sex with was Natalie. Things were still going wonderfully between us. We had become very much in love. I could seriously not foresee a life without her. The sex with Natalie was very good, too, but after all the experiences I had had with other girls, having sex with just one girl was becoming a bit old. I knew of at least two occasions when I was 95% sure Natalie had been with other guys during this time, and I was getting the itch to search elsewhere for someone else of my own. Before I got together with Natalie, I had only had sex with two other girls. My first girl was a girl I started dating and had my first sexual experience with when I was 16. I ended up dating that girl for 9 years. After that relationship came to an ugly end I found a friend of mine to have sex. I was in a dark place after the end of my relationship, and she helped me through it. It was not long after the second girl and I had sex that I got together with Natalie. I found it odd that I went over a decade having only three sexual partners and in the last few weeks I had doubled that number. I was really enjoying this new found sexual adventure.
I considered calling Allison, she did tell me that she would be willing if I ever called her seeking a rendezvous, but I also wanted to try something different. Shayna’s boyfriend was due back from overseas very soon, so I knew she would not be willing to have another go with me. Then I started thinking about Rachel. My time with her had been amazing, and if what she and I had been trying to do did not work, it might be worth trying again.
Just as I was thinking about possibly calling Rachel to see about trying again I received a text message from her. It said that she needed to see me a.s.a.p. and to come over if I could. I was not doing anything, so I replied that I would be right over.
I really did not know what to expect. Was she thinking the same thing as me about trying again? I did not know for sure, but one thing I did know was that I wanted to try again.
When I arrived at Rachel’s home I went up and knocked on the front door. Rachel opened the door and invited me inside. She shut the door behind me and then gave me a hug. She leaned in and kissed me. It was not a passionate, open mouth kiss, but it was on the lips and it did linger. It was not the type of kiss between two friends. It was much more than that. I suddenly got excited, thinking that perhaps this visit was going to be what I wanted it to be. Rachel led me into the living room and told me to have a seat on her couch. She had a large L shaped couch in the room and a chair that sat across from the couch. A low coffee table separated the two. I took a seat on one end of the couch, but to my surprise Rachel sat in the chair across the room. How were we going to have sex when we were on opposite sides of the room? Perhaps I did not know what this was all about.
Suddenly I was thrown for a loop. Dana popped her head around the corner from the kitchen and asked if I wanted anything to drink.
“No, I’m good” I answered. I was very confused at this point. Obviously this was not about sex, but if it was not, then why was I there, and why in the world was Dana there?
Dana was the final member of Natalie’s close group of friends. I did not know her that well because she and Natalie did not hang out together very much. I was some told long ago that while they were friends, Natalie and Dana did not get along very well. Rachel and Dana, on the other hand, were the best of friends. They worked together and were very close. While she was not an unattractive girl, Dana was the least sexually appealing of Natalie’s friends. She was around 5’5” tall. She was not as plump as Allison, but she did have wide hips and gentle curves. She had brown hair that came to her shoulders. From what I could tell from looking at her though her always modest clothing she had smaller, but still nicely shaped breasts. All in all she was not the most attractive of girls, but was not at all ugly.
She was currently planning her wedding to a guy named Cody. I had met him a couple times, but was not impressed. He seemed to be a socially backward man. He was also not very intelligent. He was very nice though, and he seemed to make Dana happy, so who was I to judge? The wedding was supposed to take place in a few short months. Natalie and I had been invited to attend.
Dana came in from the kitchen with two glasses of lemonade. She handed one to Rachel in her chair and took a seat on the far end of the couch I was sitting on. The girls sipped their drinks, and nothing was said.
Finally I the curiosity was too much for me. “What is going on guys?” I asked.
The girls laughed to each other. There was obviously something I was missing. “Ok,” Rachel started, “I’ve got something to tell you.”

“Okay…” I said.
“I’m pregnant!” Rachel said, very excitedly.
“That’s great!” I said. I was happy for her. “Congratulations” I added.
“Thank you” Rachel said.
“You’re welcome” I replied.
“No, thank you” Rachel said again, emphasizing the ‘you’.
“Umm, for what?” I asked. I knew exactly what she meant, but as I glanced toward Dana I wondered why she would be so forthcoming about it with her around.
“You know exactly what for,” Rachel said, “and so does Dana, so it’s ok. Don’t worry about it.”
“You… you told her?” I asked, swallowing hard and wishing I would have accepted the offer for a beverage.
“Of course she did” Dana said. “Besides, I knew Sam couldn’t do it, so I knew it had to be someone else.”
“Oh,” I said to Rachel, still concerned, “well I am still happy for you and for Sam. I am glad that I could help.”
“Well, if you are up for it, we have one more thing that you could help with” Rachel said.
What did she want now, I thought. She’s already pregnant. And what in world was Dana doing here?
“Ook….” I said.
“Well, it’s actually me that needs help” Dana said.
I just looked back and forth from Dana to Rachel. One of the two of them had better start making sense soon, I thought.
Rachel said, “You know Dana and Cody are getting married in a few months, right?”
“Yes” I said.
“Well, before her wedding, there are a few things Dana wants to do” Rachel continued.
I suddenly realized where this might be going, and I honestly was getting a little excited. “And that would be…?” I asked.
I guessed Dana must have been very nervous about all of this, because Rachel was doing all of the talking, but at this point Dana suddenly blurted out “He won’t touch my butt!”
We all laughed. I was really not expecting that, or any of this for that matter.
“Right,” Rachel said, “one of the things she would like to try before the wedding is anal sex. From what she has told me, Cody refuses to do anything back there, and since you were so willing to help me we thought maybe you would be willing to help her out too.”
I was shocked. I could not believe this was happening. At the same time, though, I was incredibly turned on. I had always been interested in trying anal sex, but none of the girls I had been with were willing to try it. “I think I may be able to help you with that problem” I said.
“Good!” Dana said, obviously excited.
“I have just one question,” I continued.
“What?” Dana asked. She seemed nervous again. Perhaps she was afraid I was not actually going to do it.
“Not that I mind,” I said, “but if that’s what you want, why is Rachel here?”
Rachel answered my question by standing up and walking toward Dana. “Well, the reason I am here,” she said, “is to help Dana with the other thing she wants to do before she gets married.” With that, she was now in front of Dana. She took Dana’s hands and pulled her to her feet. The two girls looked into each other’s eyes and they began to kiss.
My jaw fell open. As I watched Dana and Rachel were making out. Rachel wrapped her arms around Dana’s waist, and Dana rubbed her hands up and down Rachel’s upper arms and then to her chest. I started thinking that Dana had obviously been as interested in Rachel’s breasts as I had been.
Suddenly I realized what was going on. I was brought her to join in, not just watch. I got up from the couch and walked over to where Rachel and Dana stood kissing. I stood beside them, my hands roaming over their backs and their butts, squeezing both. Rachel had a firm, tight butt, whereas Dana’s was fuller and softer. I could not believe that soon I would be playing with it, doing things I had wanted to do for a long long time.
The girls broke their kiss. Rachel leaned toward me, and we kissed. We made out for a few moments, and then I turned to Dana. I leaned in and she and I shared our first kiss. Dana was a shy kisser, not seeming to want to open her mouth to me. I knew that is probably seemed odd to her to be doing this with someone other than her fiancé, but I pressed on, wiggling my tongue into her mouth. If we were going to eventually have anal sex, she needed to get comfortable with doing things with me right away. Soon her and I were making out like teenagers.
Dana and I kissed for much longer than Rachel and I had, but we finally broke our kiss. During the time that Dana and I kissed, her hands never left Rachel’s breasts. Rachel seemed to notice Dana’s interest in them and pulled her shirt over her head. She wore a leopard print bra that was very sexy, but neither Dana nor I wanted to look at it. I moved my hand up and unhooked the bra, and Dana pulled it off. After Rachel was topless she and I helped Dana take her shirt and bra off. Dana never seemed to dress very flatteringly when I had seen her before so I never really realized how nice her breasts looked. They were not as big or beautiful as Rachel’s, but they were very nice.
The three of us began to make our way into Rachel’s bedroom. By the time we got into the room the three of us were all topless and Dana had removed Rachel’s pants. Once in the room Rachel lied back on top of the bed. Dana climbed on the bed next to her and began kissing her. They only kissed for a few moments before her kissing traveled down Rachel’s neck, then her shoulder, and finally to her right breast. Dana began to kiss and suck on Rachel’s nipple. I got onto the bed on the other side of Rachel and began doing the same to her left breast.
Dana seemed timid about what to do with Rachel, but I wasted no time in letting my hands roam over her body. My hand found her thigh and lightly pulled her legs apart. I began to lightly run my fingers over the crotch of her panties, feeling the damp line underneath.
Dana noticed what I was doing, and obviously wanted Rachel’s pussy all to herself for now. She stopped tasting Rachel’s breast and moved down between her legs. I pulled my hand back, allowing her access and she pulled Rachel’s underwear off of her. Dana started touching Rachel’s legs and thighs. As Rachel and I watched Dana started to touch Rachel’s pussy. Her fingers lightly ran up and down her lips, and then slowly went inside. Then Dana leaned down and began to kiss and lick Rachel’s vagina. Rachel began to moan. I knew Dana had never done this before, but she obviously thought about doing it enough times to know exactly what to do. As Dana continued to pleasure Rachel’s pussy I returned to her breasts. While she continued to orally attack Rachel, Dana undid my pants and pulled my member out. She gently stroked it while she ate Rachel’s pussy. Soon Rachel was cumming from the double team of stimulation Dana and I were giving her.
After Rachel had orgasmed a couple of times she told Dana it was now her turn. Dana rolled onto her back and Rachel went right to work giving her the same oral pleasure she had been receiving. Dana began to thrash about on the bed as Rachel licked. I wondered if this was Rachel’s first time with a girl, but I had more important things to do than wonder about that for too long. As Dana moved about I noticed that she continued to pick her back side up off the surface of the bed. Every time she did so I got a nice view of her butt, my target for the day’s activity.
I decided it was time for me to begin playing. I had Rachel get up from between Dana’s legs and I replaced her. I began by licking Dana’s wet pussy lips. I licked her clit and tongued her hole for a few moments before my tongue began to head south. I flicked my tongue along the small patch of skin that separated Dana’s two holes, but quickly found her back one. As my tongue made contact with Dana’s tight little butt hole she began to lift her legs up. Rachel moved around beside Dana facing me and helped Dana pull her legs up. My tongue went back to work on Dana’s butt. I stated lightly flicking the tip of my tongue around her hole, and then slowly began to push it inside.
Dana was moaning very loudly as my tongue slowly entered her backside. I pushed it into her and pulled it out again several times. The taste of it was different, but not bad. The idea of doing this to her, and knowing what was to come next were extremely exciting to me. After I had made love to Dana’s butt for several moments with my tongue and she was very wet with my saliva I pulled my tongue out and replaced it with my finger. As I was doing this, Rachel was using her fingers to pleasure Dana’s vagina.
I looked up into Dana’s eyes as she looked at me as I slowly slid my finger into her butt. She was incredibly tight, but my saliva had made her slick enough that I was able to slide my finger up to the second knuckle. As I began to move it in and out Dana was moaning uncontrollably. I knew that if I was going to eventually get my thick penis into Dana I would need to stretch her out more, so I slowly slid a second of my fingers into her. This added pressure on Dana’s backside sent her over the edge. She panted and groaned and yelped as she had a massive orgasm.
As I pulled my fingers out and Dana calmed down Rachel turned to Dana and asked “Are you ready?”
“Yes,” Dana replied.
Rachel got into her bedside table and pulled out a tube of lubricant. She took some and squirted it into her hand and then rubbed it on my rock hard member, getting it nice and slick. She then squirted some onto Dana’s backside. She used her fingers to rub it all over her hole and then pushed her fingers inside to get it ready too. It was amazingly sexy watching Rachel finger Dana’s butt.
This sexy sight did not last long though. As soon as Dana was properly lubricated Rachel got out of the way to allow me access to Dana. I moved close to Dana and lined my penis up with her hole. I placed the tip on her hole and looked into her eyes as I pushed in. It was still very tight, and I had to put a great deal of pressure in order to get myself into her. I slid about a quarter of my shaft into Dana’s butt. Dana had a look of obvious pain on her face the entire time.
At this point I stopped and asked Dana if she was ok and wanted me to continue.
“NO… I mean YES,” Dana said between moans and pants. “Please don’t stop,” she added.
I pulled my penis almost all the way out and then pushed more of myself back into her. I did this again and again, very slowly, but pushing more in each time.
“This feels sooo good!” Rachel said. With that I knew she was ready. I began picking up the pace. Soon I had a good rhythm as I fucked Dana’s butt with the full length of my shaft. She was moaning and screaming like I had never heard before. She had at least three orgasms before I felt my own building. I gave her one last, powerful thrust as I exploded deep in her backside.
I pulled myself out of Dana, both of us out of breath. I looked at Dana’s bottom and noticed some of my semen that I had just squirted into her was beginning to leak out. Rachel noticed it too and quickly leaned down to lick it up. I knew after my time with Rachel, when she did not want to ‘waste’ any of my cum, that she enjoyed the taste of it, but it did surprise me just how much she really did enjoy it.
After Rachel was finished cleaning Dana’s bottom Dana was wore out. She lied on the bed breathing heavy, looking happy and satisfied. I knew, though, that Rachel was not yet satisfied. Once Rachel was done cleaning Dana she turned her attention to cleaning my member. After she licked me clean, she continued to lick and then started to suck on me. I had forgotten just how amazing it felt when Rachel did that. Although I had just had one of the greatest sexual experiences of my life my having anal sex with Dana, Rachel’s skillful mouth had me growing hard again in no time.
Rachel then rolled onto her back. I knew what she wanted. I got between her legs and immediately began making love to her. I went slowly at first, but Rachel began panting and begging me to go faster. Soon I was pounding into her hard and fast.
“Cum in my mouth” Rachel told me. I was still surprised how much Rachel enjoyed the taste, but her wish was my command. When I knew I was close to orgasming I pulled myself out and moved up close to Rachel’s head.
“I want some too” Dana said, moving for the first time since I had cum into her butt, she got close to Rachel. The two girls used their hands to help me finish and I started to cum. I did my best to shoot some into each of their mouths, but I missed some, splashing it on their cheeks and chins. They looked at each other as I collapsed into the bed and laughed, and then leaned in and licked my cum off each other before kissing passionately. I watched as the girls made out realizing I had just had one of the greatest sexual experience I would ever have.
After some time the three of us finally got dressed and I went to leave. I kissed each of the girls, telling them that if they ever needed anything again to call me and I would be right over. We all laughed as I left.

Epilogue: Judy
I sat at home one night. It was late and Natalie was out. I assumed she would not be home that night. I was almost positive she was with a guy. It was getting late, and I considered heading to bed. My mind began to wonder. I thought about what I had been through over the last couple of months. I had ended up having sex with each of my girlfriend’s circle of friends. Never would I have imagined that would ever come to pass, but I had enjoyed it very much and hoped I could do it again with some of them soon. I also wondered who else I might be able to have some fun with.
I was about to head for bed when I received a phone call. It was from Judy, Natalie’s mother. She told me that Ben, her husband and Natalie’s father was out of town and the power in her house had suddenly gone out. She asked if I would be able to come over and see what had happened. Since there was no storm or weather to cause the power outage, I assumed she had possibly blown a fuse. I agreed to go over to see what I could do.
I arrived at Judy’s house quickly and noticed from outside that there were indeed no lights on in the house. I went to the door and let myself in as I always did. As I entered the house I noticed that there were several candles lit and burning throughout the house.
I called for Judy, not seeing her anywhere.
“In here” she called from the next room. I looked toward the doorway as Judy came into view. As I looked on Judy came into the room wearing very revealing lingerie.
My jaw dropped. I had always thought Judy was attractive for a woman of her age, but I had never realized just how sexy she looked or how amazing her body was.
“Maybe you can help me with something else first” she said to me.
I realized that my sexual adventures were just getting started.
THE END
Thank you for reading. Once again I implore any and all who have read to comment at [email protected] . I am planning on at least two more chapters to this story, so if you enjoyed and would like more please let me know.

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