That Sleepover with Sam

"How long will you be?" Sam text me, eager to get the first pint down. We had arranged to meet in a pub after work. Our girlfriends were away together for the weekend so we planned some time together. Drinks in the local on Friday night, followed by a walk around London on the Saturday and then a house party on the Saturday night. Sam had to run some errands on the Saturday so I would be alone for a few hours but that didn't bother me.

No longer than 3 minutes later than that text, I was in the door looking for him.

"I'm over here". He stood and waved so I could see him in the crowded room. I rushed over and dropped my bag by his chair.

"How long you staying for? A week?" Sam enquired, pointing at my admittedly large bag. See, I had packed more than just what was 'needed' but I'll get to that soon.

Over the next 4 hours, we talked about everything we usually do; work, girlfriends, sex and politics... not necessarily in that order! We were both happy with everything. Beautiful girlfriends, great jobs and good prospects for the future.

*****

After a few too many beers, we set out on the 10 minute walk to Sam's house. When we arrived, he showed me to my room which was up the hallway from his, separated only by a shared bathroom in between. We sat on the sofa and cracked open another beer each, put some comedy on the TV and stripped down to our pants. We were comfortable with this, having known each other for about 10 years - there isn't anything either of us haven't seen of each other.

Sam had clearly had a couple too many, as he started to share his newfound love of slightly abnormal porn. Nothing weird, just bondage, pegging, crossdressers and chicks with dicks. I had to admit this had been part of my masturbation routine for a few years now. My girlfriend had never been one to partake in this kind of sex, so porn was were I could really love my fantasies.

When Sam told me that he would love to be in one of these pornos, I knew it was my time to make a move. I told him to stay put for 5 mins while I go and grab something. The reason my bag was so big is because I bought some of my crossdressing stash. Knowing I might get some time to myself that weekend, I decided to spend some time dressing up by myself.

The bag had a few essentials; a pink skater dress, a matching black lace thong and bra, some opaque tights, a mid-length, brown curly wig and a pair of black strappy heels. I had brought my makeup but there was no time for this right now.

I had shaved that morning so was still smooth all over, which made pulling up the thong and tights so sensual. I quickly clipped on the B cup bra and pulled the dress over my head. Placing the wig on my head carefully in the mirror, I then strapped on the heels and I was done. Looking in the mirror, I was annoyed I didn't have time to do my makeup, but was too drunk to care that much.

My heart was pounding as I walked down the wooden hallway, hearing the clicking of the heels on the floor. I slowly opened the living room door to see Sam had flicked the TV over to porn and had his hand down his pants. Not surprisingly, he was what seemed to be lesbian porn at first, but then a penis appeared between one of their legs. This was good, I hoped he would be in the mood to see me.

I don't know what I expected Sam's reaction to be. Perhaps he would have a laugh and turn me away. Perhaps he would have some questions. I never expected him to do what he did.

"Shit, you are hot!" he whispered as he slowly stood up, tent fully pitched in his pants. He made his way over to me and walked around me.

"I never noticed how nice your ass is!" he exclaimed, firmly placing his hand on my right buttock. He then moved to stand in front of me. With my heels, I was slightly taller but that didn't stop him moving in for a kiss.

"Woah, are you sure?" I asked as I backed away slightly.

"Hell yeah" he said as he pushed in for a kiss. I never expected my Friday to finish with me kissing my best friend as I was dressed like a woman!

I kissed back as Sam's hand lifted up my skirt, grabbing my ass harder. His hand pressed in between my asscheeks, pushing against my hole. I slipped my hand down his pants to grab his 7 inch dick, now fully erect. As I stroked it, I couldn't stop thinking about how much I wanted it in my mouth. Still under the influence of booze, I dropped to my knees, pushing Sam onto the sofa. I quickly took his dick into my mouth. This felt amazing! Using my left hand to stroke his length, I took his balls in my right and the majority of the shaft into my mouth. I worked my way up and down, proud of how I was doing for my first blowjob.

Sam pulled me up so we were both standing. He unzipped my dress and dropped it to the floor. Pulling my tights down, he sat and motioned me to get on top. Reaching for a pot of lube under the sofa, he pulled my thong to one side and rubbed it into my ass, slipping a finger or two in to loosen me up. This felt so good, I could only moan and throw my head back. Sam kissed my neck and grabbed my hips, prompting me to lower myself onto his dick. He slowly pushed his way in, I only felt pleasure - perhaps because I had practised on dildos before. I pushed his hands away to take control, and one rose up to tweak a nipple under my bra which felt amazing.

He lost control and started to thrust into me, our moans getting loader together. I could hear and feel his balls slapping onto my ass, making the experience even hotter. He pulled me down for a kiss while thrusting at full force. I could feel something change, his dick got harder and started to twitch. All of a sudden he made a big noise and I could feel my ass fill with his come. This was the horniest I had ever felt, and without my dick being touched, I came the hardest I had ever come into my panties. After two last, longer thrusts, I sat there staring into his eyes, both of us wondering what had happened but weirdly with no regrets.

To be continued...