I was giving a talk at a community meeting about 40 minutes from my home. While talking I saw an obviously sissified but very cute chub who was staring at me and fidgeting in his seat. He was constantly adjusting his pink golf shirt, his black shorts and shuffling around in his femme looking ankle socks and gemmed our Converse sneakers. His legs were smooth and supple, his man boobs were cute, his face was pretty and his black hair was short but long enough to run his fingers through.
I love sissies. I love making them feel like a girl and I love using them like a girl for all my fetish needs. Seeing this particular one made my cock rage in my pants as I spoke.
After my speech I sat down while other presenters talked. I noticed my sissy got up to go to the bathroom and I followed. My sissy went into a stall but I noticed he was just standing in there somewhat hidden as I walked in. We were far enough from the meeting and I locked the door behind me. I walked across the bathroom floor and into the open stall. My sissy was standing in a very feminine position with one foot arched as “her†knee was bent, nervously looking at me with one finger in “her†mouth. I asked, “Were you waiting for me?†I got no verbal answer but my sissy's face turned red. I moved in, took the finger out of sissy's mouth and replaced it with a deep tongue kiss. Mmmmmm this bitch tasted good. I felt up those sissy tits, fat ass and could feel a tiny clitty cock hardening in those black shorts. “Wanna get out of here?†I said and in a few minutes after some more kissing we snuck out of the community center to my car. I was done and could explain the day after that I had a call.
I quickly determined that my sissy was called Nick. I immediately renamed her Nikki. Nikki drove with a neighbor and texted that “she†left and took another ride to go home.
I explained in the car that I loved sissy girls like Nikki and I wanted to feminize her and take her to a motel to play. After some convincing kissing, petting etc “she†agreed. I loved the feel of her smooth sissy legs and thighs. My cock raging hard at what was to come. We stopped at Walmart for a few supplies like condoms, lube and of course a black nightgown, cheap but sexy heels, lipstick, nail polish and my favorite, several pairs of pantyhose and stockings in tan black and white.
Back in the car for more kissing. I realized quickly that Nikki loved the humiliation of having to stand on line with what she was soon to be wearing and getting fucked in. On our way to the motel I made her put on the lipstick and to swap out her sheer black ankle socks for a pair of sheer tan knee highs that I also bought. You can tell I like stockings etc.
I gave Nikki cash and forced my sissy to walk in to the clerk and get our room. Watching Nikki have to go in with lipstick on and the sheer knee highs showing from her ankles to her knees because she had on shorts and her sneakers was exciting. I should have made her wear the heels!
Nikki came out beet red and we were off to room 227. Once in the door we were tongue kissing again. I had Nikki stripped down to the knee highs pretty quickly. What a sexy smooth chub Nikki was. Just a cute triangle of short hair over that tiny clitty. We showered and got Nikki on the bed. As I sat in the chair I watched as she obeyed my commands. First fixing her lipstick. Then painting her toenails in that candy apple red we chose. As the nails dried the sexy sheer black nightgown went on and then when her nails dried, it was time to choose what stockings or pantyhose to wear. I decided on the suntan sheer to waist pantyhose. It made Nikki's ass sexy and touching her clitty through the soft hose was intense. Her pretty toes looked sexy in the nylon as she then Alison her high heels and stood up off the bed for me. We kissed and kissed as I touched that body all over. Finally I threw Nikki down on the bed and had my way. I exposed those sexy chub titties from the top of the nightgown and sucked on the two smooth C cups making the nipples rock hard. I tickled Nikkis clitty through the soft nylon as my hard on raged. I tot fucked Nikki good and then watched as “she†took my cock deep in that pretty sissy mouth. Her hunger for my cock was incredible. It took great concentration not to cum. I pulled out of that hot mouth and began to kiss Nikki all over. Especially all over her pantyhose covered clitty, ass, legs and of course, after those high heels came off, those very feminine looking hosed feet. My cock was leaking Pre cum like crazy and my sissy was panting heavily. I must mention that I also tickled Nikki intensely making her giggle and yell loudly that she would do anything if I stopped. And we did just about everything. We were both getting to that point of maximum overdrive. That's when I ripped a hole in the ass of her pantyhose, got on my rubber and lubed that bitch up good. It felt so good to fuck Nikki missionary style so I could pound that fat ass hard and deep as Nikki toyed with her clitty cock moaning. I held her ankles up and kissed licked and sucked on her feet and legs as we fucked harder and faster. Nikki was saying all kinds of kinky shit as I talked dirty to her. Once she blurted out, “I finally feel like a real girl!†I felt my orgasm coming on. Pounding her hole and enjoying her chubby sissy body with the soft silky pantyhose driving me wild I came like a 7.0 earthquake. With those stocking covered feet and legs at my disposal to enjoy I flooded the rubber to the max and was still pumping hard for another minute or so. Then Nikki started to say she was getting close. As she was about to orgasm I was already out of her ass. I took off the condom and she begged me to pour the cum from it into her mouth. As she took the load she came hard from that tiny clitty but soaked her pantyhose good. After that we rested a bit.
Next we followed up by a fashion show with the other stockings, a sexy nylon foot job blowjob combo and we fucked twice more before heading home. When Nikki got dressed to go home I made her wear nude pantyhose under the shorts with her sneakers. Nikki is 22 and still lives with Mommy and her straight twin brother. Watching Nikki go into the house like that was exciting. We see each other every week or two and now the sex is bareback. Nikki is now my Nylon wearing Sissy Fetish Slave. Nikki's collection of femme clothing is getting sexier, even sexy Halloween costumes are involved.
Best part is that nobody ever asked where we went during that community meeting.
