My First Time

I knew it was a bad idea from the start.  I picked up the phone that night, knowing what would happen but somehow convinced myself that it wouldn’t.  I had been engaged for all of four months now and I knew I shouldn’t make this call.

This was my first time.  Throughout our relationship I had been faithful, going so far as to turn down anonymous sex once or twice.  I don’t remember what came over me, but in a moment of weakness, I dialed her number.  Bailey answered, “Do you want to come over?”  No hello, no how are you, just “Do you want to come over?”  “I’ll be there in 30 minutes.”

Bailey and I had a strange relationship.  I was pretty sure neither one of us really liked the other.  A few years before we had hooked up and had amazing, toe-curling sex.  But that’s about it.  No dinners, no movies, just fucking.  We were both reasonably young and used each other to explore the limits of our sexuality.  As my relationship with my future wife developed, I stopped calling Bailey and she stopped calling me.  I didn’t miss the sex at all, at least not until this night.

I knocked on the door and tested the knob.  The door was unlocked so I walked inside and saw Bailey sitting on the couch in the living room, wearing just a tiny, tight tee shirt and panties.  She walked to me and her hands went to my crotch as she planted a very steamy kiss on my open lips.  “You’re engaged now, so I’m pretty sure you didn’t come over to chat.”  She dropped to her knees and started fumbling with my zipper.  My hearbeat raced; a combination of the excitement of the situation and the beautiful blonde on her knees trying to get my cock out of my pants.  She succeeded, pulling my hard cock out of my jeans and swallowed it whole.  During our previous “relationship”, Bailey grew from your average college girl to a sexually confident woman.  She knew what I liked and she knew how to please me.  After about five minutes of this attention, she stood up and beckoned me to follow her to her room.

Once in the bedroom, I pushed her roughly over the side of the bed and pulled her panties down.  She knew how much I loved the sweet taste of her pussy and how aroused I got when she was freshly shaved.  She didn’t disappoint.  Pulling the flimsy panties down, I buried my face in her, spreading her ass to get to her plump, soft lips.  Though she didn’t need any help getting wet, I loved to suck, lick, and nibble on her beautiful pussy.  The saltiness of her arousal made me even harder, wanting her even more.

I threw my jeans off and pushed her forward on the bed a little.  Guiding my cock towards her, I used one hand to hold her fast against the bed.  Her pussy was so tight that, combined with the strange feelings of cheating, I almost came at once.  Regaining my composure, I started to pound her harder and harder.  Bailey always enjoyed it a little rough and this time was no exception.  I reached forward and started tweeking her clit in time with my thrusts.  She started to groan as I hammered away from behind her, a sure sign she was going to cum.  As her orgasm hit I had to focus all my energy and will on not shooting my load too soon.

As she regained her composure a bit, she reached back and grabbed my cock.  “I know what you really want,” she said, pulling my slick cock from her cunt.  She guided the head to her asshole, pushing her hips back a little and working my cock up and down in her ass.  I had been the one to introduce her to anal sex and, although she was skeptical at first, this soon became one of our favorite adventures.  “I bet she doesn’t let you fuck her here,” she hissed as my head entered her ass.  She got the answer about thirty seconds later when, just as I was starting to fuck her faster, she clenched her ass around my cock.  With no warning, I screamed out that I was cumming and started pumping my cum into her ass.  The orgasm coursed through my body, almost making my knees buckle from pleasure.  As the waves of pleasure subsided, I slumped forward, laying on top of her as my cock softened in her ass.

This would be the last time I saw Bailey.  She calls or emails maybe once a year, generally when she has just ended a relationship or is looking for a reason to end one.  Every so often she sends me a picture taken with her camera phone.  Last night I answered my phone to find a grainy shot of her, leaning over the side of her bed, some guy’s cock buried in her ass, with her looking over her shoulder, smiling.  “Thinking of you” was the only message.