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Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more
I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play.

She knew I liked ass play from conversations about things we'd done in the past and I held no secrets back about how I really wanted to explore those feelings further. So Saturday after breakfast we drove down to the big city to go toy shopping and ended up at this totally sketchy sex toy and S&M shop. We stuck close together and finally found what we were looking for; a strap on harness that would take various sizes of toys. We bought the harness and a dildo that seemed about life-sized. We were completely embarrassed with our purchase and I could tell the guy behind the counter was having fun at our status as total sexual novices. We couldn't leave the store fast enough for the sixty mile drive back home.

Once back at the room, Lili told me to get completely naked and sit in her makeup chair. She didn't want to fuck a man, she wanted to fuck a woman. This wasn't at all what I expected, but she always had a way of taking things that next step beyond where I was comfortable, which is what made our sexual explorations so exciting and dangerous. After expressing my concerns, she promised me I wouldn't have any regrets in the morning and I decided to play along. While I got undressed she slipped out the door and returned with a bucket full of steaming hot water, a can of shaving cream and three Gillette twin-blade razors. I thought I knew where this was going and I wanted no part of it, but in the end her threats to not follow through were all I needed to comply.

The process of shaving me was slow and meticulous. She didn't want to miss a spot. She started at my ankles and worked her way up, not leaving me with even a tuft of hair at the base of my cock. She even went so far as shaving my chest and armpits. I was one bald son of a bitch. She then proceeded to rub me down with floral scented lotion, careful to avoid playing too long with my aching erection. The feeling of her hands gliding over my smooth legs was unreal and it changed every sensation in my body. I felt more feminine, vulnerable, and delicate than I ever had before in my life.

After the shaving and lotion application was complete, she put me in a pair of her laciest panties and bra. My erection poked out the top of the panties, the bra felt amazing and I was starting to enjoy my transformation from robust male to feminine flower. She then proceeded with doing my makeup. Again, this took a lot of patience, probably more for her than for me this time since I was freaking out with that mascara applicator brush so close to my eyes. In the end the look was phenomenal. She borrowed our neighbor's heavy metal, hair band-style wig to top things off, put me into a Coors Light half-shirt with my midriff exposed and a short black skirt and crammed my feet into her three inch, red pumps and the look was complete. ...Almost. She decided I wasn't walking like a woman, so she told me to bend over and inserted the largest butt plug we owned, a monster that stretched me to the limit. She put my panties back in place and said, "I'm hungry, let's go get dinner." No fucking way. No. Not going to happen... and again, she won out.

She promised me that I was completely passable as long as I didn't say a word. She promised to order for me and told me I just had to act like a lady and the illusion would hold. Easier said than done, but I was committed now and walked on wobbly ankles down to the dorm's after-hours pizza joint. It was a Saturday night and the place was busy. Two things amazed me. First off, in a dorm with only 250 rooms, nobody recognized me. Not one person. Secondly, I had guys actually giving me the eye. I was an actual head-turner!

Standing at the counter waiting to order almost ended in disaster. My body took that moment in time to decide to relax my sphincter and I almost dropped the butt plug with a half-dozen people in line behind me. I quickly turned to back into the counter and awkwardly pushed it back up inside of me. I'm not sure what those around me though just happened, but that was the one time I got a bunch of very strange looks. I clinched my ass as hard as I could until we sat down and I whispered to Lili what just happened. She laughed out loud as we walked to the table to wait for our order.

When we returned to the room she told me how turned on she'd been the entire time and said she was ready to be my man. She told me to sit the bed and without getting undressed, she opened the front of her jeans and revealed the strap on. I had no idea she'd been wearing it the entire time we were eating. I was so self-conscious that I never noticed her bulge, which must have been quite substantial in her loose-fitting blue jeans. In any case, now confronted with the dildo right at face level she told me it was time I learned to suck a cock. Again, I didn't see that one coming at all. This was an anal fetish, not an oral one, but when in Rome...

It was not easy. It wasn't easy at all. I had no idea just how hard it was to take something that big even just past the head. She had me lean back and bent over me to reach the lipstick. She freshened me up and said I needed to show her just how deep I could take it and leave a high mark on the dildo. I tried to oblige, but she chided me on my poor performance. She pulled back and showed me that I was barely taking an inch and a half in my mouth and she expected at least half the length in my mouth before we could move on. I gave it several more attempts and in frustration she started grabbing the back of my head and forced me to take it. I gagged several times, but I was learning I could take a lot more than I originally thought. I was tearing up from gagging and a wicked smile started across her face. She said, "That's what it feels like when you start thrusting your hips while I'm giving you head. I want you to remember this." I was in tears now, struggling to time my breaths to her thrusts and doing what I could to just swallow that massive member. After what seemed like an eternity, she relented and said she was proud of me for taking it like a man. I'd made a high mark at almost four inches.

She told me to stand up and turn around and place my elbows on the desk counter. She told me to reach back, pull my panties down just a few inches and spread my ass cheeks apart. I obliged and I felt her heat as he moved near. She was still fully dressed and, well, so was I. I felt her pull out the butt plug and I felt the head of the dildo pressing against my ass. She hesitated to apply some lube and slowly pressed in. I was already warmed up from the butt plug, but I was in no way prepared for the length that was to follow. She listened to my cues and proceeded slowly. She told me to look back at her over my shoulder and watch her as she slowly slid the cock into my ass and I adjusted to the thickness. I relaxed and she slid deeper and deeper inside of me. Deeper and fuller than I'd ever felt before in my life. It was bliss. She asked for some reassurances and I let her know that I was ready to take it all. She told me that was all of it. I felt giddy with excitement knowing I'd taken a man-sized cock all the way to the hilt up my ass.

She started to find a rhythm and I matched her tempo. I moved my elbows to the counter and started grinding back to meet her thrusts. She reached around and started playing with my bra and my nipples underneath. The whole thing felt amazing. I was ramming back to meet her strokes now and she asked me again if I was ok. I told her I needed her to fuck the living shit out of me and she grabbed my hips and began pounding me hard! I was pushing against the cinder block wall to keep my head from bashing into it and she was pounding the living fuck out of me. I was losing my mind in the overwhelming sensation and my body was in overload. I wanted it all and that's all I could take.

Eventually we had to stop. My ass was starting to get worn out, but I still hadn't come. She gently pulled back and hesitated at the head. I stopped her at that bulbous end and she slid back in. Ahhh, it felt so good, but she needed to pull out. With careful tenderness, she slowly withdrew the head and I nearly collapsed. I laid down on the bed and she climbed on top of me, still dressed in my heels, panties, bra and half-shirt. She put the head of my hard cock inside of her and started to tease me at her entrance. She reached down and started playing with herself and told me to visualize myself as the receiver, like I had the vagina and she had the cock that was playing at my entrance. I closed my eyes and visualized myself with her cock pressing at my entrance.

The visualization worked and I started feeling her cock sliding up inside me. I felt myself riding it, feeling it opening me up, filling me, and focusing all my attention. As she rode me and played with herself, my own orgasm was building. This had been a day filled with hours of foreplay and it was time for sweet release. Her tempo was relentless and she finally settled into grinding on top of me, gnashing our pubic bones together and I felt her begin to tense and buck. That was all the added stimuli I could handle. My cock jumped and began spilling into her. She collapsed on top of me and we embraced on the bed. I don't recall either of us moving until about 6:30 the next morning. As we both came to life, we smiled and laughed and the train wreck we'd created in the room, from my destroyed makeup to the dildo and butt plug lying on the floor. We had some cleaning to do before her roommate returned.

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