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jennypout
Over 90 days ago
Fluid Genderqueer, 28
0 miles · New York

jennypout stories

Sissy Submissive

A secret submissive is enthralled by a female visitor.

We were having a guest run a meeting for us. We were all seated around the usual round conference table. She was standing on the other side of me. The first sight of her was riveting. A tall woman, beautiful, with long straight dark hair, wearing a black skirted suit, the skirt pencil tight, the short jacket buttoned over a white blouse, both tight over her bust, the shirt unbuttoned enough to show some cleavage. Best of...

Office Sissy 3

A sissy in the office is used by a female co-worker.

The meeting the day before, at which I'd told everyone in the office, in extensive detail, about all of my preferences and fantasies and desires, had been an incredibly exciting experience. It was all verbal, no one even touched me, but exciting nonetheless to have revealed myself as a helplessly and easily arousable submissive sissy. I told them all how much I loved to crossdress and be treated as a sexy little girl, tol...

Exposing Myself To A Group

A new sissy is taken to a crossdressing group and fun ensues.

Rachel decided it was time for me to come out to others more than I ever had. She did some research and found that a meeting for trannies was taking place at a motel just outside the city. She took a room and checked us in, then we had dinner and went to the meeting room. The room was in a large motel suite. We arrived early. Rachel had dressed me and I was definitely 'out'. I was wearing open-toe wedge sandals, my toes p...

Office Sissy 2

My sissy office life continues.

I was now back in the office, but under wildly different circumstances! I had dutifully confessed everything to all of the co-workers, bosses and staff, the previous day. Now everyone knew about my girly submissive self. And my recent changes in dress - the girly look - were fully explained. As part of it, I had had to tell them about all my secret thoughts, feelings and actions. I told them how aroused I always was whene...

Office Sex 6: Two Sissies Playing

Two sissies talk and play.

Now that 'Becky' had fully revealed herself and played with me and others so openly, 'she' was very responsive to suggestions. So when I told her to come to my office the next morning early, there she was. In contrast to me, though, she was still wearing her usual boy's clothing, a suit and tie. I was in my usual girl's clothes, in this case, panties and a short-skirted cotton sundress with a halter top, short-heeled sand...

Office Sissy 5: Sissy Babies

Two sissies find a mommy and daddy in the office.

After 'Becky' and I found each other, and played together in my office, I convinced him to finally be open about his true nature. Together, I was sure we could find lots of pleasurable scenes in the office if everyone knew about him, just as they knew everything about me. So that night, on his own, he agreed to shave himself smooth, and to come to me the next morning for the reveal. I had brought in some baby supplies, in...

Milked On The Train

A young man is touched and seduced while traveling to school.

I was still a virgin, at my advanced age (17), but aroused a lot, loved reading sex scenes in books, imagining it, touching myself. I traveled every day on a crowded train, on the way to my classes. One day I was standing, as usual, holding on to the pole while the train rocked and slowly made its way. An older man, maybe forties, was holding on to the pole across from me. He was taller, holding on lower on the pole, and...

Office Sissy

A new office sissy meets a mistress.

Now that I was l spending time with Chris, (sissy) and Rachel, (in charge), I was feeling girly as I never had before. It affected the way I looked. I was keeping myself shaved smooth, all over. I polished my nails (toes and fingers). I was wearing tighter pants and shirts. I usually wore sandals, without socks, my polished toes peeking out. One day I was sitting in my office and an officemate, Sheila, appeared at the doo...

Office sissy 4

Two sissies find each other in the office

It was the third day at the office, in my new role as the office sissy, and with the new rules, which allowed anyone there to play with me. I was in my office as usual, but I had brought more clothes in. So this time I was in a bikini, meaning a thong bottom and a bikini top holding my flat titties. Both were in matching light pink, which always seemed the right color for me these days, and the thong was barely enough in...

The Neighbor

A sissy meets a mature neighbor.

I had moved into a new apartment complex. One great benefit was the outdoor pool, and I had taken to lounging there most days. I was still enjoying being out as my natural self. So that meant I did a fair bit of mincing around in a bathing suit that was too tight. I otherwise kept it restrained. So my nails were not polished and my look was otherwise natural, without make-up. I had a ground-floor apartment at the corner o...