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.

First Time Strap-On Play

As I sit down to write this, my hands still shake a little.  About 5 years ago I started hanging out with Courtney.

Courtney is about five years younger than me and an absolute fucking machine.  Over the three years we hooked up, there was nothing I could cook up in my sick little mind that she wasn’t willing to at least try.  Be it a threesome with her suitemate from college or a foursome with my two best friends, this girl was an absolute freak.

Courtney called me one afternoon and asked me to come over to her dorm room.  Since it was a beautiful weekend, her roomies had decided to head to the beach but she didn’t feel like going.  For some reason we had not hooked up in almost a month.  Nothing was wrong, but we were both busy and didn’t seem to be able to connect with each other.  During the previous week, Courtney had left me a few suggestive voice messages, promising me an unforgetable weekend.

She called me on Friday afternoon to confirm that the girls were at the beach and the entire apartment was hers for the weekend.  She mentioned that she had found something that I might be interested in, but refused to tell me any more.  Since I had never gotten close to the limits of her sexuality, I had no idea what she had in mind.

After work on Friday, I headed to by buddy’s bar and gave her a call.  Normally not one to miss the chance to go drinking, I was amazed when she said that she was staying in Friday.  Courtney was only 20 at this time, so she almost never gave up the chance to go out, especially when she knew no one would card her.  I explained that I would like to have a few drinks to relax from the weekend and she replied “You might want to have a few extras, just to loosen up.  You’re never going to guess what I have in store for you…”

When the phone went dead, I was left with a beer in my hand and my jaw on the floor.  I couldn’t even imagine what she had in store.  I hung around for about another hour, drinking steadily and running over the possibilities in my mind.

I got to her place about 8:30.  She answered the door in a baggy pair of sweats, her hair up, and no makeup.  Not that she was unattractive, but she normally liked to get a little dressed up if we were staying in.  I was the first guy that bought her lingerie and she absolutely loved wearing just about anything that showed off her body.

She opened a bottle of wine and we sat down on the couch.  After a few minutes of normal conversation, she asked me if I trusted her.  She went on to explain that she had indulged many of my fantasies and, although she enjoyed them all, she wanted me help her live out hers.  Why not, I thought to myself, what could she possibly want to do that I haven’t already jerked off to…

She led me to her suitemates room and helped my out of my pants.  Her roommates had a little grudge going: each of them liked to fuck on the other roomie’s bed, in the name of harmless fun.  So we were in the other room, the lights turned down a little, but her figure still very clear as she walked around the bed.  I was laying on my back, pants off, feet on the floor, and my ever hardening cock beginning to rise.

“Close your eyes.”  I did and my head started spinning with the possibilities.  I could feel her get closer to me, kneeling down between my legs and taking my cock in her mouth.  She spent a few minutes getting me hard before pulling my cock out of her mouth with a loud pop.  “Let me know if this makes you uncomfortable.”  With that, she took the whole length of my cock in her mouth as she started to play with my asshole.  First it was just the one finger, playing outside my hole.  As she worked harder on my cock, she started getting a little more aggressive with my ass.  She grabbed a little lube from the table and coated her finger.  I don’t know how to describe the feeling of her finger entering my tight ass; a combination of pleasure and uncertainty.  On her knees, she worked the shaft with her mouth while she played with my balls and toyed with my asshole using her free hand.

“What do you think of my finger?” she asked, taking a break from blowing me.  “Uh, well, it’s different, but not painful.  When your whole finger is in there, I feel like I’m going to cum really quickly.”  “Should I stop, or keep going?”  Since she had not stopped playing with my cock as she talked, I was getting really close to cumming.  “Keep going”, I implored her.

With that, she stood up and I noticed that she was completely naked, standing between my legs with my hard and wet cock in her hand.  She bent over at the waist and fumbled with something on the floor.  As she stood up, I noticed something was different, but with the low light I couldn’t tell exactly what it was.  She turned sideways and it all became clear.

“I found this in Jenny’s room last weekend” she said as she squirted a bit of lube on the strap on cock now firmly fitted to her waist.  My eyes bulged, but I didn’t move.  It was about my size, just under 7 inches long, but a bit thinner than my own cock.  My eyes were glued to the fake cock; even as she told me the story, I was focused only on her toy.  “I noticed a strange noise coming from this room last weekend.  I knew Jenny was hooking up, but something about the noise was unusual”, she explained.  It seems that Jenny is even kinkier than I imagined.  This is the same girl who agreed to a threesome with Courtney and me.  But I had no way to know how genuinely dirty she was.

The next morning, after the guy left, she asked Jenny about the strange noises.  Blushing, Jenny explained the whole thing.  The guy she was hooking up with was into strap-on play.  Jenny, like Courtney, was open to most suggestions and, though a little put off by the request, agreed to play along.  The guy brought over his “favorite” toy, the strap-on setup that Courtney was now wearing.

Without any further ado, Courtney moved between my legs and told me to move my legs onto her shoulders.  “Just let me know if I need to slow down” she instructed as she lubed up her fake cock.  With my ass in the air and my legs over her shoulders, she started to rub the head of the toy on my ass.  Already lubed up from her finger, she didn’t waste too much time on this, choosing instead to work just the head of the cock into my rear hole.  Now, I have convinced more than one girl to let me try anal with them and try hard not to make the first time hurt too much.  As I felt the head press against my ass, I thought back to my instructions to my anal-virgin partners.  “Take a deep breath and as you feel the head push against your ass, relax.  As the head goes in, keep breathing and push a little.  This relaxes the muscles and will keep anything from hurting too much.”  Always seemed to work for me, but it’s a whole different story when it’s your ass.

So I started breathing and as the head popped in, I pushed a little, just to ease the pain and help my ass get accustomed to the visitor.  Before I knew it, Courtney was all the way in my ass.  To start, the pain was pretty intense, but as she worked up a little speed, it subsided and the fullness in my ass became more and more pleasurable.  Just as I was starting to get used to the feeling of her in my ass, Courtney bottomed out in my ass, thrusting deeply as she played with my cock.  The sight of her beautiful tits bouncing as she stroked my ass and played with my cock was just too much.  Before I could warn her, I erupted, shooting long, thick strings of cum all over our stomachs.

Pissed at me for cumming too quickly, she jerked the cock out of my ass and grabbed me by my hair.  “You goddamned pussy” she screamed, “you can’t even take a solid assfucking.”  Pulling me off the bed and onto my knees, she grabbed my chin and ordered me to lick my cum off her.  Overwhelmed by the sudden change in tone, I didn’t know what to do, other than stick out my tongue as she forced my mouth to her stomach.

The sudden shift in her mood foretold a change in our relationship, but I was too overwhelmed to notice at the time.