Ryan’s dilemma

First attempt at a story, let me know what you think.

This was an unexpected turn of events for a Friday night. I had planned on spending the evening on a wonderful date with my girlfriend. She already knew what the plans were, she never liked surprises. Me being the romantic type, this took a lot of fun out of the relationship for me. We were to begin the evening at a fantastic, and very expensive, restaurant. She had wanted to go ever since her best friend’s boyfriend took her there. I wanted to take her this evening and tell her about the raise I received at my job. All my hard work and overtime paid off finally. With the new position and extra cash, I figured we could finally start expanding our horizons. I was going to tell her about this right before I proposed to her. The ring was my mothers, and was passed down from her mother. Things changed as I was putting on my suit for dinner.
As my phone rang, I thought about letting it go to voicemail. I was having so much trouble with my tie that I figured maybe I needed a break and the phone call would calm me down. As I looked at the incoming number, I started to smile. It was Tia, my girlfriend. I imagine she was excited about going to this extravagant restaurant and wondering what the special occasion was.
“Hey beautiful, are you ready for dinner?” I asked grinning from ear to ear.
“I’m sorry but I can’t make it tonight. Something came up” she stated. I could hear that she was holding back tears.
“What’s wrong, did something happen.”
“Look there is no easy way to put this,” I heard her sigh as if she was thinking about whether she should keep going, “I don’t want to see you anymore.” With that she hung up but not before I heard her start crying.
This was really weird, I couldn’t think of why this could happen. Many thoughts raced through my mind. What could make her break up with me all of a sudden? Maybe she heard about my little incident a month ago. Now that wasn’t the only time something has happened but it was the only time that I wasn’t careful about what I was doing. I couldn’t help but remember what happened.
It was a rainy night and I was in the next town over. I had been at a party and was in no condition to drive. My friend who came with me had disappeared earlier with a very pretty girl. No telling when I would see him again. I started to look for a quit place to rest and sober up. On my way, a girl was struggling to get away from some creep that was way drunker than anyone else in the party. I went to help her but tripped. It didn’t look like I tripped, but it did cause me to bump into the guy and free the girl. I said sorry and tried to explain but the guy swung at me. I saw the punch but was to slow to move. Luckily, the guy was way off target and just fell. He didn’t move so I figured he passed out.
“Thank you so much. Some people shouldn’t drink if they can’t hold their liquor. My name is Keisha.”
“My name is Ryan, and it was an accident really.”
She looked me up and down. The grin she gave me let me know that she liked what she saw. I never considered myself a stud, but after a few drinks everyone thinks they are the best looking thing in the world. At 6’, 190 lbs, and pretty athletic from different sports I played in my spare time, I felt pretty good about myself. With the look she gave me, I had to check her out. She was 5’ 5” with light brown hair, and a very nice body. Her breasts looked to be a 36D from the look. I couldn’t help but grin as well.
“I was looking for a place to sit and sober up. Maybe you could sit with me and talk for a while” I said nonchalantly.
“That sounds like a good idea,” she glanced around the room as if looking for a good spot. “Maybe we should go upstairs.”
“I thought no one was allowed upstairs. Maybe we should ask the person that’s throwing the party.” I stated remembering that my friend told me that the person who was throwing the party was real stuck up and would start some shit if she caught anyone breaking her rules.
“I know the girl who lives here, she is a really good friend of mine. She won’t mind if all we do is talk,” her smile was increasing as she talked.
“I heard that she can get kinda bitchy if her rules are broken. I don’t really know her but I don’t want to mess up the chance of coming to another party.” I don’t know why I said that but liquor has a way of making you tell the truth.
“My friend can be a bitch but if you were to explain it to her, she would understand.”
I started wondering who was in charge of the party, I never thought to ask or even considered wondering until now.
“Let me introduce you to the host of the party, come with me.” She led me up the stairs into a room. We had to scoot past a couple of people on the steps, but the upstairs was completely empty. “Hi, my name is Keisha. I hope you like my house. This is my room, you can lay down in here and sober up some. And no I won’t get bitchy about you being up here.”
My mouth dropped when she told me, I tried to make up an excuse but all I could do was stutter. She laughed at my failed attempts to speak and pushed me into the room. The only place to sit was on her bed. The room was pretty plain except for some stuffed animals she had laying around. I figured we would start talking about what happened but boy was I wrong. She walked up to me and was stripping as she came closer. As the last button came undone from her shirt, it slipped to the floor. At this point, I completely forgot about my girlfriend. No other words were said. I stood up and started kissing her softly, my hands caressing her bare back. I found the zipper to her skirt and had that undone in no time. I took a step back to admire her beautiful frame. She had a hungry look in her eyes and had my shirt up and off along with my pants in record time. I wasn’t going to argue with this beauty, instead I followed her lead and got the rest of her clothes off. She pushed me to the bed and started kissing down my chest. She stopped at my abs and started licking and caressing down to the edge of my boxers. She looked up at me with that infectious smile and continued her journey down while removing my boxers at the same time. I was hard since she started stripping, but when my 7” member came into view she gave a quick gasp. She started to stroke up and down my shaft with slow strokes. After admiring for a short time, she took the head into her mouth and let out a soft moan. I was in heaven as a stared down at her face. She would look into my eyes from time to time and I would hold her gaze when I could. As her head bobbed up and down, I couldn’t help but close my eyes. After a few moments, I had to taste her. I motioned for her to come up but she wouldn’t release my cock. So instead of making her stop, I pulled her up into a 69 position. I received my first view of her luscious pussy lips and was amazed to see a piercing there. This was the first woman I have seen with a piercing down there. I gave it and her clit a little lick. She shivered at the first touch of my tongue and I delighted in the taste of her pussy as well as the feel of the cold metal. I began my assault on her clit but didn’t neglect her cunt lips either. I was alternating between tongue fucking her and nibbling on her clit. She released my member long enough to let out a loud moan.
“Yes keep that up. Please make me cum. Oh yes baby” she was saying in a loud whisper. With her praising my work, I started working harder. I had to taste her sweet nectar. I flicked her clit faster and faster. She resumed sucking on my cock with her expertise. The faster I lashed at her clit, the more she moaned on my member. I was getting really close but I wanted to hold off. I didn’t want this to end to soon. When I thought I couldn’t take anymore, her whole body shook and convulsed. As her juices started to flow, I lapped up as much as I could. After a while she pulled off of me, shaking her head that she couldn’t take anymore. I gave her a few minutes to recover and to allow myself to calm down a little.
“Oh my god, I needed that. It’s been so long,” she stated. I couldn’t imagine why she would go without. She was a beauty and could easily take her pick of any guy she wanted. “I’ve been to busy working and with school. That is why I threw this party, just to relax and forget about all that. But now I have other things on my mind and we aren’t done yet.” That explains that and who am I to argue about her plans for tonight. With that I stood up and repositioned myself between her legs. I started kissing and sucking on her neck but didn’t stop there. I planted kisses down to each of her breasts. I stopped to suck on her left nipple while my hand caressed and fondled her right. Her moans were getting louder and she was squirming like crazy. Finally I started to enter her slowly, enjoying the feel of her lips around my member. I couldn’t help but moan at the feel of how tight she was. Remembering that it has been a long time for her, I tried to go slow. As I made it to half way inside of her, I couldn’t take it anymore. My lust took over me and I plunged the rest of the way in. She let out a sharp gasp at the intrusion and I wasn’t sure if I hurt her. I stayed still to let her get used to the feeling. After a minute, I slowly started to stroke in and out of her with short strokes. When she started pushing back and matching my thrust, I began to pull further out until just the head was in. Her muscles gripped me as if they didn’t want me to exit. As I pushed back in her velvety grip welcomed me back in. I was enjoying each and every second of this. It wasn’t long before I felt the churning in my balls. As my pace quickened, she must have sensed my need.
“Yes, give it to me baby. Cum inside me, I need this,” that was all the encouragement I needed. I was pumping away like crazy. My muscles were beginning to burn and up until this point I didn’t realize how long we were going at it. I still wasn’t sure about the time but I didn’t care as the cum started moving up my shaft.
“Yeah baby here it cums, damn you feel so good. Oh my god” I uttered as all I had rushed up to coat and cover the inside of her tunnel. This was the biggest spurt of cum that I let out in a long time. I lost count of how many times I spurted inside of her. I was supporting myself on my forearms but could barely hold myself up by the time I was done. I allowed some of my weight to fall on her and started kissing and caressing her neck and chin. As I was kissing her, I couldn’t help but notice her shivering and convulsing. In my drunken rampage I didn’t even take time to consider if she was enjoying herself. But as sensitive and receptive her skin was to my touch, I knew she had came. Every touch left goosebumbs on her skin. As I started to finally get soft, I slid out of her. She let out a soft moan as my cock left her tunnel. Both of our juices pooled on the bed under her. It was a few moments before either one of us spoke.
“That was amazing. I don’t know how I could go so long without sex. I must of come 5 times. I came so hard that now I’m hearing ringing” she stated. Ringing, oh shit my phone. It must have been going off for 5 minutes and I didn’t even realize.
“Sorry that’s my phone going off. I completely lost track of time. But that was amazing and I would love to do that again.” That was the only thing I could think to say. I knew it had to be my girlfriend calling. Shit, what kind of excuse could I give? I could always say I got drunk and forgot. Wouldn’t be the first time that this has happened.
“Did I keep you from something important? I’m sorry, I didn’t mean to get you in trouble. I just wanted to thank you from getting me away from that jerk downstairs. He has been stalking me for some time now and won’t take no for an answer.”
“It’s ok, I didn’t have any plans for the night. It might be my friend Josh that I came with wanting to make sure I got home ok,” I lied. “He’ll understand under the circumstances. Plus he ditched me tonight so let him sweat a little.”
We began talking for a little while and got to know each other. She was 25 yrs old, a year younger than me, and has been on her own since she was 21. She used to live with a friend until she got a raise at her job. That is when she moved into this place, and threw parties on special occasions. I told her about my job and the school I was going to. We talked for a few more minutes, but with both of us still naked she couldn’t help but notice that I had been aroused again for quite some time. When she couldn’t ignore it any more, she began to stroke my cock again. At this time, I figured it was ok to start kissing her and that is what I did. While she continued stroking my member, I began fondling her breast. I loved how firm they were and the way her nipples stood at attention. I broke the kiss and began sucking her nipples into my mouth, first one then the other. Her hands left my cock and went to the back of my neck pulling me closer. My left hand was caressing her back while the right rubbed up and down her slit. I began to lay her back on the bed and continued my feast on her breast. The battery on my phone must have died because the ringing finally stopped. There must be a million messages by now but who cares. She pulled my face back to hers and started kissing with more passion than before. Our tongues danced together for minutes as I continued rubbing on her clit with my thumb and inserting two fingers inside of her hot tunnel. She started stroking me again. Her pace began to quicken the more she became excited. Her breathing was getting labored and I could tell she was close. I went back to her breast and gently nibbled on her nipples, she stopped stroking me as her body shook through another orgasm. When she finally came down from her climax, she turned over and got on her hands and knees. I had to take a second and admire the nice ass that was in front of me. I was still a little tipsy from what I had to drink, but it doesn’t take a rocket science to figure out what she wanted me to do. I climbed into position behind her. My left hand caressed her cheeks and felt how firm they were. As my right hand grabbed my cock and rubbed her slit, I had to thank my friend for leaving me stuck or else I wouldn’t of ran into this angel in front of me.
“Take me. Please put that dick back inside of me,” she yelled from over her shoulder. “Fuck me hard, I need this.” That was enough for me, I gladly complied with her demand. She was completely drenched, so there was no need for niceties as I shoved in balls deep. She let out an Uh as I filled her with that thrust. She started convulsing through another orgasm then, it must have been a really long time since she has been fucked. With that I began ramming her with full long thrusts. I gave into my animal lust with her moaning while matching each thrust of mine with her own. I took one hand and gripped her hips, pulling her into me. With my other hand, I began to play with her clit. I could hear her chanting yes, yes, yes, yes, with each thrust. I wanted this just as bad as she. With me cumming earlier, I knew this was going to take a while. Even though I didn’t know her that well, I decided to test the waters. I took one hand, and licked my thumb to get it wet. I began rimming her asshole, hoping she wouldn’t reject my advance.
“Ooh baby, how did you know that I like that? Go ahead and push that finger in there. I haven’t had anything back there in a while.” Wow, this girl was a nymph. I’ve never found any girl that would let me try anything back there, she was encouraging me to. She even admitted that she likes to do this. My dick was well lubricated from our earlier orgasms, so I withdrew from her wonderful hole. I couldn’t resist the temptation I felt, I’ve always wanted to try anal and here was my chance. Even with all the juices on my rigid pole, I couldn’t help the urge to tongue fuck her ass first. I gave a few licks then began stabbing into her hole as far as I could. She let out a constant mmmm as I continued lavishing her hole. My cock started to hurt from anticipation, so without waiting any longer I lined up my member for this wonderful treat. I knew that this could be painful and that I had to take my time. I gave a gentle nudge and wasn’t surprised to find some resistance.
“Go ahead, push it in baby. Give it to me.” With coaching and encouragement like that I almost gave in to the urge to plunge straight in. I did apply more pressure and watched as her ring swallowed the head of my cock. The feeling was intense since this was the first time that I could actually find someone willing to give me this pleasure. It has been a fetish of mine for some time now, and I was living a dream now. She let out an uhh as I penetrated her. Realizing that I could have hurt her, I sat still letting her adjust. She started pushing back against me so I gave her a little more. Working in and out, I couldn’t help but think that her cunt was tight but damn. Even with all the lubricant, I was still having trouble moving in her. I applied more spit to my cock and to her hole. Soon I found myself halfway into her. With slow strokes I continued to ease into her. After a few minutes I was finally all the way in her. I sat still relishing the feeling and giving her time to adjust. I felt her shudder some more.
“I miss this feeling of being full,” she stated. I felt her hand move down and start playing with her clit. Why couldn’t I have met her years ago when I was still single? As her fingers moved faster, I began fucking into her again. She continued to amaze me. Not only was she matching each stroke, but I could feel her fingers moving inside of her cunt. She was fingering herself really fast so I decided to ram her just as hard. She must have been close cause she was mumbling something that I couldn’t understand. With all that was going on, I knew I couldn’t last much longer. I began fucking as hard as I could, trying to make both of us reach the climax we both wanted, we both deserved. Sweat was boring from both of us. The noise from the party seemed to fade and not exist anymore. The only thing in our world was us as we strained every fiber in our body to reach this bliss that was so near but seemed so far.
“I’m so close baby, yeah keep pumping. Fill my ass with your seed. Give…. it……to…….me” she yelled as her orgasm finally peaked. Her muscles contracted so tight that I couldn’t move. They began to milk me and bring me over the edge. Even though I was trying to shoot, my dick was confined so tight that it hurt. When she finally relaxed, I was able to let my seed burst out in full force. I don’t know how many times I squirted, but there was so much cum that it was leaking out around my dick. The feeling of my seed shooting into her must of set her off again. Her muscles clamped down on my member once again. Even if I wanted to leave her confines, she wouldn’t let me until she was done.
“That was amazing” I stated. This was by far the best sex I’ve ever had. To make things better, I just met this girl.
“You are the biggest I’ve ever had, no bullshit. I’m glad that I did meet you tonight.” I think she was just trying to make me feel good, how many times has a girl said that you were the biggest she’s ever saw.
“Shouldn’t you check and see how the party is going?” I asked.
“Yeah, and I think you sobered up enough to drive home.”
As we began to get dressed, we exchanged phone numbers. She reminded me that she has a very busy schedule and doesn’t always get time to have fun, but any free time she got she would make sure to give me a call. As we walked down the stairs, the party was still in full swing. We had been upstairs for two hours and nobody even missed us. She walked me to the door holding my arm the whole way. I originally came with a friend and didn’t know anyone here, or so I thought. As we made it to the door I gave her a kiss goodnight. As I turned and started walking to my car, I ran into Tia’s best friend Kim. She stood there with a wicked grin on her face. I wasn’t sure what to expect. Kim has always had a crush on me and even though I was with her friend, she would still flirt with me behind Tia’s back. Even with me turning down all her advances, she would still try little things to try to get with me. She even went as far as to come out of the shower naked at Tia’s house when she knew I was there. I told Tia about all her tricks and games but she would just laugh them off and make excuses for her friend. In this situation I knew Kim would either mess up my relationship or try to blackmail me. I hurried to my car as quick as I could and threw my phone on the charger. I was always better when thinking on my feet in drastic situations and this was one of them. All kinds of scenarios raced through my head. I checked my missed call list, almost all the calls were from Tia except for a few from Josh. I called him to see if Tia had called him. He said he never heard from her and asked what happened to me. I told him I would explain later.
The next day I got my stories together and called Tia. I told her I went to a party with Josh and he ended up leaving with my phone. I had to explain that his phone died and he borrowed mine to make a call and I didn’t see him till today. She asked about the party and I gave her a few details, leaving out the incriminating parts. She told me that she was going to go to a party with Kim but wasn’t feeling to good. Knots started to form in my stomach. Is she trying to tell me that she knows or is she being honest? I sat silently waiting until she continued. She said Kim must have had a good time because she hasn’t been home all night and her parents haven’t heard from her. I thought maybe if I talked to Kim I could figure her angle but I knew it would be impossible to talk to her without Tia being around. Tia started talking again bringing my attention back to her. She wanted to meet up later and get together so we made plans. While we were out we ran into Kim and some guy she was with. Kim was smiling the whole time they were talking. I made small talk with her friend and secretly tried to listen in on them. I kept fumbling and dropping my keys because I was so nervous.
“Is everything alright Ryan, you seem to be somewhere else” came Kim’s remark as her grin grew wider.
“Still a little hung over from last night that’s all.”
Her smile seemed to grow wider or maybe it was just my imagination. She kept glancing my way as she continued her conversation with Tia. I waited for her to try to approach me, whisper a threat, or even just blurt out the fact that she caught me cheating. That moment never came. Honestly, she never brought it up at all. For a while I thought I dodged a bullet. I had nothing to hold over her head since she didn’t have a steady boyfriend and didn’t keep anything she did a secret. She wasn’t an outright slut, but she could be easy at times. The rest of the day went normal. Me and Tia even ended up having sex at the end of the night. Everything seemed great since then.
I had forgotten all about that day until now. Even though me and Keisha only talked a few times after that, we never hooked back up. Maybe Tia came across something and Kim ended up telling her about that night. I wanted to know how this could happen out of the blue. Everything was going so well between us and now this. What can I do?

To be continued……hopefully.

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