Explorations beyond my expectations


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 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, Beşevler escort Bayan 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 Çankaya escort 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 Cebeci Escort 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.

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