Backdoor Sissy: First Time Feminization, Crossdressing (HOT ADULT TRANSGENDER AND CROSSDRESSING)

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TLDR: Through some mix of alcohol, emotions from a very recent breakup, longing for an adventure, and sexual frustration, I finally got up the courage to dress up and visit someone. It was significantly more intense than I anticipated, in a scary way...10/10 would do again. First-ever time Sissy teaching FIST with no-hands orgasm! 5 months ago 23:20 ShemaleMovie train, first time, fisting

I was at the edge of the bed so that my nyloned feet were hanging off, wrapped up like a gift waiting to get used. My legs frogtied together and unable to budge, wrists tied to the rope around my ankle, all I could do was lay there waiting with my face buried into the bed unable to look around. Finally I heard foot steps on the hardwood flooring in the hallway, then silence as he stepped into the carpeted room.We had arranged this meeting for weeks with my bull, he understands all things sissy and he had seen Stacey come on leaps and bounds since we had first met. He was excited too and he told me he was going to treat her just how all sluts deserved to be treated. Below I am going to go into detail about how we got my husband to this point and I’ll let you know what it feels like, how to make the most of it, and how Stacey handled her first ever anal creampie. Stacey Was Always Used To My Sloppy Seconds I had moved away from home to go to college at 18. I had been cross dressing secretly for a few years. I would sneak into my mom's closet and "borrow," her clothes. I had my own apartment my parents were helping to pay for. I also had a part time job and was able to buy a few feminine clothes for me to wear. I loved the feeling of wearing women's clothes but, was not very experienced sexually. I had one girlfriend in high school and she was the limit of my sexual experience. He laughed and said, "I didn't know you were a faggot and I'm definitely am not, so NO, I don't want you to do that to me."

Sissy very first Time Dressing Up For dad 6 months ago 26:35 ShemaleMovie crossdresser, first time, erotic, game, dress He starts moaning and saying, "oh yeah sweetheart here it comes...!" As he emptied his balls into me, I could feel every splash and spurt against my insides and all I could do is smile. Finally, I had done it. I was no longer a virgin and I could honestly say I loved every bit of it. May Sissy Cumpilation 3 weeks ago 12:05 VideoSection crossdresser, anal, cumshot compilation, feet, first timeSissy uses Lube for the first Time and Absolutely Loves It! 4 years ago 17:27 TrannyGem sissys first time Sissy Fingering Tight Ass for the first Time and Eating own Cum 4 years ago 07:39 TrannyGem sissys first time I had left a request for the garbage disposal to be fixed earlier in the week but, didn't figure they would be out on Friday afternoon. I tried to ignore the door but, the maintenance guy must have heard the tv and used his master key to get in. He entered and saw me dressed. After I left, I sat in the car for a minute and just tried to compose myself. Taking a few deep breaths and just thinking about what had transpired, all I could do is laugh and put the car in gear. Once I arrived and met up with the girls, my ass still squishy from his cum, they all noted how I had a different glow about me... My first-ever time as a sissy was so liberating 11 months ago 15:09 ShemaleMovie mexican, crossdresser

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So, that is how it all got started. Of course, now, I wear make-up, a dash of perfume. my hair in ponytails, I shave off all my body hair and I wear girly clothes for him. I do it all just to please him. It's our little secret. First time pegging my sissy husband and jerking off to him 7 months ago 07:28 XXXDan strapon, crossdresser First-Ever time fledgling crossdresser gets jism al over by sugar dad 2 years ago 14:25 TrannyGem sissys first time We found out my husband had a kink for sissy play early on in our marriage and although I was hesitant about it at first, I heard him out and we tried to incorporate things into our relationship that would sexually satisfy him. It started slow, things like him wearing my underwear, playing with his ass, dressing him up like a woman, etc, and it soon flourished into something beautiful. Fix that attitude. A good sissy should want their ass to be ravaged." After which he then again proceed to push all the way inside me in one thrust. Again I cried out in pain, but this time he didn't pull out and only pressed harder against me and spanked me another time. "What was it you said when we were messaging?

Heterosexual Boy Humped by Trans Nymph for Very First Time 1 year ago 08:47 TrannyGem sissys first time Very first time unexperienced crossdresser gets jizz al over by sugar daddy 2 months ago 14:35 ShemaleMovie crossdresser, first time Sissy trans Artemis Asteria gets intimate with roommate for the first time 6 months ago 11:34 AnySex first time Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. Before I knew it, my bull was beginning to cum inside of her, he began shooting his load deep inside of Stacey, filling her up with his cum, he kept on thrusting into her hard as he loaded her up and treated her like nothing. Stacey squealed with girlish delight as she felt my bull depositing his load inside of her, she moaned into the bedsheets, urging him to carry on but everyone knows that sissies don’t make requests like that or they must face punishments, I would deal with that later.

That's more like it." Purposefully misunderstanding my pathetic pleading. "I bet your pussy hurts after taking a pounding like that for so long." Japanese crosssundresser first time to dress up 8 months ago 15:19 ShemaleMovie crossdresser, dress No", I replied, "today just felt right...that's not the last you'll see also" as I started pulling down my pants revealing the thigh highs. Emo crossdresser plumbs her contorted satan ASMODEUS for the very first time 5 months ago 10:16 KeekAss insertion, goth, emo