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Letting Out My Secret free porn video
Well it started innocent enough.
I had been secretly crossdressing for quite some time now and had a few real meets under my belt. But it’s been a long time since I dressed. With a busy schedule and other responsibilities to tend to, I’ve been finding it hard lately to devote time for myself and my “hobby”. I’m able to still find a little time for CD/TV porn and reading sexy stories about first timers. I’ll sometimes fantasize about being the one in the video or pretending I was the one having fun in the stories I read. Of course I still keep my girl clothes, heels, wigs, make up, and lingerie stored nearby for that spur of the moment event that I might find the time to do a little dress up.
Well one night I was chatting on messenger to my close female friend about something totally unrelated. I have known her for over 20 + years and consider her a very close and loving friend. I don’t have very many guy friends and we both have families of our own. We do however fool around when we get the chance and we could almost always talk about anything, including sexual fantasies, without taking things serious or personal.
Well the conversation later turned to crossdressers and transvestites. There had been something on the news that day about the gender restroom issue and we digressed to the Rupaul drag race show and how much a man could look so much like a woman with the right help and motivation. That’s when she told me that she thought I would look good dressed as a woman.
I was kind of shocked at first that she would even say that. I mean no one knows I’m a crossdressing transvestite other than me. No one’s ever saw me that way except the ones that I had met in the past but then again they never seen me in guy mode either. So my true identity and my alter ego’s was never compromised. But in the same way I felt excitement on how she would respond if I told her my secret. It’s kind of like I wanted to tell her since I’ve known her for so long and knew my secret would be safe with her.
I responded to her with something like, “Do you really think so?” I even said maybe you could be the one to do my makeup and dress me. When she answered “sure, that would be fun” I felt even more comfortable about telling her. I then asked, “do you think it would turn you on seeing me dressed as a girl?” that’s when she told me that she was sometimes attracted to seeing a guy in drag that there was just something about it that turned her on.
That’s when I told her that I use to dress fully as a transvestite. At first she thought I was full of it. I told her it was a long time ago and that no one knows. She still didn’t believe me and started asking several questions like where I got my clothes and make up and all the stuff needed. She asked where did I dress at and what did I do. After realizing I had answered quickly to all her questions she began to believe me but I still felt she was unsure. I told her I could prove it with pictures and videos that I had stored on my computer. She said, “Ok, I’ll believe it when I see it.”
I then sent her a few pics. She sounded so surprised at what I had just proved to her and commented on how pretty I looked. She even added how turned on she was when she was able to see the video of me that I had also sent to her. I told her I’m not very good with makeup and that’s when she offered to help me next time I dressed.
Well next month rolled around and I told her I’d have a night off and that I really wanted to take her up on the offer of her make up help. We planned on a night that she was unable to take off. She does work the graveyard shift at a nearby motel and said just get a room and I’ll make you up when I have a little down time. I was all for it and even got the room at a discounted rate. Of course I selected the ground floor near the rear doors so I could bring my dress up back in and not draw so much attention.
I checked in before she arrived for work. An older man was working the desk and I didn’t have any problems checking in and getting my bags to my room. She wasn’t due for work for another hour and it gave me time to go through my clothes and lingerie and pic something to wear. After deciding on an outfit I set it aside so that she couldn’t see what I was going to be dressed in until after she did my makeup.
Well after a brief nap she arrived to work. She actually arrived early and had time to do my make up right away. It did feel particularly strange having make up put on without being dressed first. But I wanted to do it that way to get the “surprise” effect when I do show her. She did my eyes in somewhat of a bronze shade and a darker color lipstick then what I’m used to. Foundation and powder first of course. I really couldn’t look at myself made up without my wig and being fully dressed so I decided to get ready. I told her to leave while I do so and she clocked in at the front desk to begin her paperwork for the night.
Well I dressed in a short tight dress, nude color stockings and black heels. I admired myself a little while and just loved the job she did with my makeup. I then texted her to tell her I was ready. She arrived back to the room a short time later and couldn’t believe it was really me. She was admiring me too and it appeared she liked what she saw. She began to touch me and rub my legs as if to see if I was for real. I think she was a little in shock. But she did say I made a very pretty woman and she did believe me finally about me being a crossdresser. So that point was proven.
Well as usual when I dress I get a little sexually aroused. Thoughts start racing in my head as to what exciting or girlie things I could do. I suggested walking down the hallway to her and said that she had to go back and check on things. Apparently there was still some overdue reservations that she needed to attend to. I told her when she gets another break to stop back in. well about ten minutes later I decided to walk the hallway. It was a pretty quiet night and didn’t think anyone would see me but the rush would be exciting if someone did. So I left out of the room and walked down the hallway towards the front desk. I practiced strutting and shaking my ass hoping maybe some guy would open his door and catch me. I heard music coming from one room but that was it.
I made it to the front desk and surprised my girl friend again. She was like, “what are you doing? Are you trying to get caught and have people see you?” I was like”yeah, that was the point….lol”. I told her when she had a break to stop by my room because I had one more secret for her. Her curiosity arose and wanted to know more but I said she would find out when she gets there. She said she had one more reservation to wait for and she would be back at the room.
Well I started to get a little horny all dressed up. I watched a little bit of crossdresser porn on xhamster to kill some time. About a half hour later she knocked on the door. I let her in and again she started to touch me and rub my back while we were hugging. She even lifted my dress to see my red lace panties I was wearing. She asked what her surprise was. That’s when I retrieved my 7” realistic dildo strap on out of my bag.
She said “what’s that?” and had a look of fear on her face. As if she never seen one before. I think she thought I was going to use it on her. I said, “You’ll see” as I knelt down in front of her and fastened it around her waist. I think what I did next wasn’t what she expected at all. I told her, “You want to see what dressing like a girl does to me?” I then began to suck on the dildo pretending it to be a real cock. I held it with both hands stroking it as I moved it back and forth in my mouth. I looked up at her and she had such a surprised look on her face but then a turn on face at the same time. I think she liked watching me pretend I was sucking her fake cock. I also could feel my boner getting very hard in my panties. I took them off exposing my gurl clitty from underneath my dress. That turned her on even more and she grabbed the back of my head trying to get me to go further down on the rubber dick.
After giving her that pretend blow job I asked if it turned her on at all. I stood up and reached my hand down her pants and rubbed her pussy and could feel it very wet. I then asked if she wanted me to fuck her. She immediately said yes. I then told her, “Only after you fuck me first”. I grabbed my bottle of lube from my bag and threw her on her back on the bed. The realistic dildo still strapped to her and poking straight up. I rubbed lube on it and slowly mounted her. I think she was really freaking out but again turned on at the same time. I moved my hips up and down on it trying to get it in as far as I could go. I would moan a little with each downward stroke. And that’s when she got more into it. She began to tell me,”yeah that’s it, fuck that dick you slut.” That just made me move faster. I couldn’t get it in all the way but I just liked the fact that she was enjoying it as much as I was. I got off of her and had her spoon me on the bed. Again only getting it in so far but feeling her hips rock with the strokes. My hard clit couldn’t take much more. I turned back around and unbuckled the strap on. I then pulled off her pants and panties at the same time slid my hard clit in her wet pussy. It was her turn to do the moaning and pushed my clit in her as far and fast as it could go. I could still feel the soreness of my boi pussy and it felt like the fake cock was still inside me. I finally couldn’t hold it in anymore and had the most wonderful orgasm as my cum dripped out of her pussy as I pulled out my clit.
After laying there for a moment she got dressed and had to check on the front desk. I told her I better get some rest and call it a night. After undressing and putting my clothes away she texted me that it was the best fucking she’s had in a while and loved my new gurl persona and couldn’t wait to do it again sometime.
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