When I first started dating Cindy, I had no idea how “experienced” she was sexually. She was 7 years older than me; I was 24 and she was 31. Now don’t get me wrong, I am a good looking guy and had plenty of sex before Cindy, it had just mainly been your run of the mill, exchanging oral sex and then trying a few different positions type sex. Very good, very fun, but not much beyond that.

However, I quickly found out that Cindy had done more than that. While playing a game of “I never” one night, I found out that she had been involved in a threesome with a guy and a girl, had sex in a public bathroom, had sex with an old boyfriend in college while her roommate watched, and a few other things that I was surprised to learn.

I didn’t quite know how to take it all at first. Obviously I had no delusions of her being a virgin or anything and I had no problems expanding my sexual boundaries. I guess it was a bit of a disappointment that she had these experiences in general, while I hadn’t.

Heading home from the party we talked about these new discoveries and how we felt. And it obviously helped me when Cindy made the following revelation:

“You know, I love you very much, and this should make you happy,” she explained. “While I don’t necessarily need or want to do everything I’ve done in the past, there’s still lots I would love to try and to do over again with you.”

We got home a little after 1 a.m. and were feeling pretty good after quite a few drinks at the party.

“Why don’t you take off your clothes and get in bed to wait for me”” Cindy requested. I happily obliged.

She returned to the bedroom a few minutes later wearing a black bra, black stockings and garter belt and nothing more. No shirt, no jeans and no panties. She was a sight to behold – 6 feet tall, shoulder length blonde hair and an athletic build. I was in heaven and she remembered me mentioning before how much I love a women in black underwear!

“So, let’s start fulfilling some of your fantasies! I’m up for anything tonight. What is something you’ve always wanted to do that no one has let you do so far?”

I stood up out of the bed and walked over to Cindy and kissed her on the mouth, pulling her to me passionately. I wanted her to know this was something I appreciated. But I then wasted no time moving from a show of appreciation to a show of what I wanted. I pulled away from the kiss.

“On your knees,” I commanded!

Cindy slid to her knees. Catching on quickly to the role we were playing at the moment, she looked up at me and waited for her instructions.

“Suck my cock!”

She moved her head forward, stuck out her tongue and guided my half-hard cock into her mouth without using her hands. She quickly had my cock at full mast and slid those delicious lips from the tip of my cock to the base over and over again. It was an incredible blow job. Nice and warm and wet as she sucked me off. She had never blown me quite like this before. She was sucking me in, sliding her tongue along the bottom of my shaft. Occasionally she would deep throat my 6.5″ cock a few times in a row before going back to swallowing three quarters of the length. Each time she deep throated me I could hear her gag a little. God, that slight gagging – not choking her to the point where she couldn’t breathe, mind you, just a little gag – was getting me off so quickly.

I grabbed the back of her head with my right hand and started thrusting my hips forward slightly, fucking her mouth a little.

“Look at me while you’re sucking my cock.”

She looked up at me with her beautiful blue eyes while I fucked her face.

“OK, now suck my balls and jerk my shaft a little.” She took her mouth off of my shaft and started licking and sucking my balls. It had been a long time since anyone had sucked my balls and it felt so good. For the first time in this blow job she touched my cock and began jerking me off, using her own saliva as lube.

“Shit! I’m about to cum,” I panted.

“Do you want me to swallow it for you baby?” she asked sweetly. But I wasn’t in the mood for sweet.

“Not tonight. I want to cum all over your pretty face!” No one had let me do that before so I was taking advantage of this situation while I could. Cindy took me back into her mouth and sucked my cock for maybe another minute and I finally reached my breaking point.

“I’m gonna cum,” I announced.

I removed my cock from Cindy’s mouth with a popping sound and began jerking my cock inches away from her face. She smiled at me and began whispering encouragement.

“Cum for me, baby! Give it to me! Shoot that load all over my face. I want your cum so badly!”

My first shot of cum splashed just below Cindy’s eye on her left cheek. I moved my cock and hit her forehead with my second shot before adjusting again and hitting her open mouth with shots three and four. I then lowered my aim and got a few weaker shots onto her breasts before being spent.

“Oh, fuck, that was amazing!” I said. “Best blow job ever!”

Cindy swallowed the cum on her tongue before asking, “Oh yeah, you like that?”

“Oh hell yes! Thank you!”

“Oh, we’re not done for the night, babe, far from it. Go get back in bad and I’ll be back in a minute after I clean up a bit.”

Cindy stood up and walked out of the bedroom toward the bathroom. I watched her ass sway below her garter belt until she entered the bathroom and I climbed into bed to wait for more.

Two minutes later, Cindy walked back into the room, fresh faced and ready for more. She climbed into bed and straddled my waist. Starring deep into my eyes, she reached behind her back and unsnapped her bra. She slowly removed the bra, teasing me a little as I waited to see her breasts. She then threw her bra onto the ground.

“Suck my tits!” she commanded. I greedily obeyed.

I raised my head and propped myself on my elbows and sucked her left breast into my mouth. I swirled my tongue around her areola several times before sucking directly on her nipple. Cindy liked her nipple play a little on the rough side so I mixed in sucking with nibbles and bites and even pulled her nipples out with my teeth. Each time I did so I received a moan of partial pain, but much more pleasure as a response.

After spending a good 5-10 minutes switching between nipples, Cindy moved my mouth away from her breasts and she moved up my body until she was straddling my face instead of my waist.

“Time to repay the favor,” she announced and lowered her wet pussy to my face. I happily obliged and ran my tongue the entire length of her slit and began eating her out. I reached around and grabbed her ass as she rode my face. I always loved going down on Cindy, but loved eating her out even more when she was riding me like this, something she saved for “special occasions.”

I licked through her lips and all around her pussy. I loved the taste and would eat her out as long as she wanted right now. Cindy kept humping my face as I licked for all I was worth, trying to give her a wonderful orgasm like she had already given me. After a few minutes, I felt Cindy move slightly forward and I knew what she wanted. I grabbed her ass checks and spread them apart and moved my tongue to her puckered anus.

Cindy loved having her ass eaten out, too, and thankfully I enjoyed performing analingus, as well. Another moan escaped Cindy’s list as my tongue flicked across her hole for a couple minutes and eventually began penetrating her backside. After eating her ass for a couple minutes, she shifted back and my tongue moved back to her pussy.

“OK, its time to get me off. Suck my clit and pinch my nipples, please!”

I did as I was asked and began sucking on her clit while rolling her hard nipple between my thumbs and forefingers and each hand. Within minutes, Cindy was coming to a screaming orgasm above my face. After recovering, she slid down my body and gave me a big kiss, no doubt able to taste her own juices on my lips and tongue.

Cindy began stroking my cock to get me fully hard to begin actually fucking. She rolled onto her back and pulled me to her. I moved on top of Cindy positioned myself between her legs and slid my hard cock into her soaking pussy.

We started screwing vigorously, the alcohol earlier in the evening doing its job in allowing me to last a good deal longer at this fast pace than it normally would. I obviously still had the revelations from earlier in the night on my mind, and as I thrust into Cindy began asking her about past experiences.

“So, you’ve had a threesome before, huh?”

“Yes.”

“Tell me about it. Who was it with? When did it happen?” I asked.

“About 5 years ago. When my friend Cortney was living in California we had a threesome with her boyfriend. He never fucked me, but he and Cortney fucked and she and I played around a lot.”

“Really?” I replied, a little shocked. “So did you go down on Cortney? Did she go down on you?”

“Yes, we both ate each other out.”

I was quite amazed; and quite turned on! As for most guys, a MFF threesome was always a fantasy and the thought of my girlfriend’s face being between her hot friend’s legs and vice versa was VERY hot!

“Would you be interested in doing something like that again?”

“I figured you would ask that,” she replied, as we continued to fuck. She continued, “That’s one of the things I’m not sure about. I enjoyed doing it and am fine with being with a woman again. But I love you very much and am not sure about sharing you with someone else. I’ve never done that with someone I care about.”

Not sharing me be damned! If she were willing to be with a woman again, I wanted to be there. After all, how often do you have the chance to make this fantasy happen?

I pressed on. “I guess I understand that, but it has always been a fantasy of mine and I’d like for us to keep it as a possibility.”

“If you keep fucking me like this, I will definitely think about it. And I have to admit, just talking about it a little is making me pretty hot.”

“Oh yeah? Well if we were going to do it, who would you want to do it with? Cortney again?”

“She’d be great; I really enjoyed having sex with her. But not sure if she would do it since she has a boyfriend now, too. I’d ask her if she were single again.”

“Hmmm, then anyone else you’d want to do?” I asked.

“I’m not really sure. I haven’t thought about it at all.”

“How about Kim?”

“I don’t think I could ask her,” she said. “If she didn’t want to I wouldn’t want to hurt our friendship.”

“Understandable. How about Michelle? Jen? Tara?” I asked, waiting for a response after each name. Each was a “no” for various reasons. Finally I asked, “How about Amber?”

A pause. Still no answer. Finally, “Yeah, I have no idea how we’d bring it up – IF we were going to bring it up – but I would do Amber.”

Amber was just as tall as Cindy and had very large breasts. Oh yes, I liked that her answer for Amber was a yes!

“But let’s talk about tonight,” Cindy changed the subject. “Anything else you want to do tonight that you’ve never gotten to do before?”

“How about anal?” I threw out as a suggestion, expecting to be shot down quickly like I had been by every other girlfriend. Instead I heard the wonderful word, “OK.”

“Really?” I asked stunned.

“Yes, I like anal sometimes. Let’s do it.”

“Do you have some lube?”

“Don’t worry about it,” Cindy responded. “I’m plenty horny and soaking wet. That should work for lube. Plus you know I like a little pain. Just go slow.”

Cindy then placed her legs on my shoulders and repositioned herself a little so her ass was exposed. I pulled out of her wet vagina and placed the tip of my cock at her tightest of openings and prepared to fuck a woman’s ass for the first time ever. Another fantasy coming true!

I began pushing and met a lot of resistance. This being my first time having anal sex I wasn’t sure exactly how hard I would have to push to enter her ass. I was trying to walk a thin line between using force to penetrate this tight hole while also trying to be gentle.

“You can push a little harder,” Cindy encouraged. “It’s almost in.”

I took her advice and pushed forward and felt her ass give way as my head pushed in. I pushed just a little past that point when I hear Cindy again.

“Ah, shit! Stop for a second!”

“Are you OK?” I asked. “Did I hurt you?”

“It’s OK. Alright, start pushing in again … slowly.”

I pushed forward. I could feel each inch slip in as her ass hole gripped my cock tightly. I got just over half way in and I could feel Cindy pull back a little, trying to control the depth. I took her hint and pulled back until my cock was almost out of her and then pushed in to just about the same depth.

I went at a controlled pace for a couple minutes, but fucking a girl’s ass for the first time coupled with how horny I already was made me lose some of that control and I began fucking her ass a little harder; a little deeper. This was amazing! And Cindy was now getting into it and enjoying it, too!

“Oh yes, fuck me! Fuck me good!”

“Where am I fucking you?

“In my ass!” she practically yelled. “You’re fucking my ass!”

“You like my cock up your ass? Huh? You like my hard cock inside your tight ass?”

“Yes! Yes! Keep fucking my ass!”

I could tell she was enjoying the ass fucking, but also still controlling the depth at which I penetrated her. It felt great, but I wanted more. I wanted to go balls deep inside her ass! I grabbed both of her wrists and pulled her arms above her head and then held them there with my right hand. Cindy loved feeling like she was being “forced.” Then I put my left hand on her thigh and pushed forward a bit so she couldn’t push herself forward to stop my dick from going in more.

“Take it! Take my cock in your ass!” I said. Then I pushed forward as much as possible and felt my cock go completely inside her ass; my pubic bone resting on her ass cheeks. I could see a look of slight discomfort on her face and loved it!

“Oh, fuck!” escaped her pretty lips.

Once I was in her completely, I let go of her wrists, put both hands on the mattress and started fucking her ass! I fucked her good and deep for a few minutes longer when Cindy asked if I was going to cum soon.

“Not quite there, but getting there,” I responded.

“Maybe this will help get you there faster.” Suddenly I felt her finger on my own ass hole. Cindy circled my ass with her finger. I thought I would have jumped and told her to stop right away, but damn it felt good! She just kept rubbing my sensitive hole while I fucked hers.

“Does that feel good baby? Do you like me rubbing your ass hole?”

“Uh huh.”

“Tell me then.”

“It feels good, Cindy. You rubbing my hole feels real good. Keep doing it.”

“Are you getting ready to cum?” she asked.

“Yeah, I’m pretty close now.”

She then pushed her finger tip into my ass.

“Oh fuck yeah!” I yelled.

“You like being fucked in the ass, too?” Cindy asked.

“I don’t know if I’d say that, but I like this. Keep doing it. I’m about to cum soon.”

I really started fucking Cindy’s ass. And every time I fucked her, I fucked my own ass with her finger a little more. I could feel her straining to try to reach around to get more of her finger in my ass. Her ass hole was gripping my cock with force now too, trying to milk the cum out of me! I then felt her push a second finger in my ass at the same time I bottomed out in her and it pushed me over the edge!

I shot deep inside her ass at the same time I yelled I was cumming. She kept thrusting her fingers into me as I kept spewing my load into her rectum. As I finally stopped cumming, she slowly pulled her fingers from my ass, and then I slid my cock out of her. A little cum flowed out of her ass as I pulled out.

“Fuck that was good!” I said.

“Yes, yes it was,” she panted.

“You know I’m not going to let the threesome idea go, right?”

She just smiled and said, “Yeah, I know. We’ll see.” And we fell asleep.

---