First Time In A Long Time

by Dave (NJ)

I had never fantasized about sex with another guy before it happened, it just happened. We were both very young. Starting innocently as watching each other changing into our suits in the pool house.

One day he walked towards me, naked. I just reached out and grabbed his almost hairless cock and guided it into my mouth. I sucked the tip for about 5 seconds then he shot a ton of cum all over my face.

So over the next 3 years we sucked and fucked each other every chance we got. I started wearing panties and stockings and he loved it. I grew to love the taste of our cum but most of all, the sensation of feeling him cum in my ass.

We both went off to college, dated lots of girls but when Home, I would get dressed to be his sissy slut. Our gay sexscapades all came to what seemed to be a reasonable conclusion when we graduated college. To this day I haven’t been with another guy.

I continued to fantasize about cock for years but I was absolutely 100% heterosexual...or so I thought. Several years ago I started using a dildo in my ass. Slowly over time I graduated to bigger ones, vibratory& plugs.

Now I find myself dressing like a sissy slut again aching for cock. I shave all the hair from my body, douche my ass, slide a very large plug in my wet asshole, pull on my stockings, tuck my cock tight, put on sexy panties, then I throw on jeans & a T-shirt and go shopping for more girly stuff.

The other day I was in a nice store and the sales girl knew exactly what I was doing. Told me her brother shops here. She actually picked out a very nice sexy sun dress for me & told me to go try it on. Staring at myself in the mirror I was so hard I came untucked. My cock popped out just as she was bringing me another sun dress.

She checked me out, closed the door then sat down and called her brother....he and I met for drinks the following Friday night. We went out for drinks as 2 guys but our night quickly brought us to her sisters house where we changed into girls.

He put on light blue stockings with garter belts, white panties & a yellow silk strapped top. I changed into black crotchless pantyhose, black thong, & a black mini skirt with a purple silk top the same as his.

We were both so turned on by ourselves and each other that we started kissing and tugging. That’s when his sister walked in. Seeing as she set us up, we shouldn’t have been embarrassed but we were...but only for a second. Then she said how we’d look better in make up..so an hour later the three of us girls went out looking like three pretty sluts.

We went to an alternate bar for more drinks. Got pretty hammered, then to a sex shop where we all bought toys. Then the three of us went back to his house. It was much closer to the bar. Billy’s sister had watched -actually encouraged him to go under the table and suck Me off for a minute at the bar. But when we got back to the house I found myself attracted to her & she knew it.

I put the moves on her and she readily spread he thighs open for me to lick her beautifully shaved pussy. Billy watched for a while then he came over and started licking my boy pussy. I then turned my attention to her brother’s dick. Slowly I started, then I really got into it. I could not believe it had been 30 years since I had sucked cock. All this was going on while we were all dressed as girls. The silk felt so good. His cock and his sisters pussy tasted so good.

Now Jessica wanted to watch her brother get fucked, so I obliged her. I topped him in various positions for about twenty minutes while she watched and tried out her new toy. Then I took her toy in my mouth. Changing condoms I then fucked the shit out of Jessica. At some point Billy came close enough for me to suck his cock. So I stroked and sucked him off until he shot his load in my mouth.

That was glorious. But I was still going at it in his sisters tight cunt. Eventually she moved and ripped off my protection. She wanted her 38 D cups to be fucked and creamed on. So I obliged. She ordered me to clean up my mess, calling me her family’s sissy slut. I cum kissed her which of course got us all horny again. So after a short rest, billy started working my ass, first with his tongue, then finally I was getting my ass fucked by another guy. My dream finally came true. So did Billy—ass to my mouth!