Crossdressing Vignettes #2 (True Story) free porn video

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This is from the early 1990s, when I was in the occasional habit of crossdressing in lingerie and bottoming. I don't do that any more for several reasons, mainly because at my age I just don't have the body for it any more.

About 20 miles from where my wife and I lived, on the outskirts of one of America's largest cities, there was an unofficial red light district. It was basically a very poor little village that had opened its boundaries to adult businesses in order to attract some kind of tax revenue. There were strip joints, massage parlors, and adult bookstores. Streetwalkers wandered the area. One night a friend got me into an i*****l crap game in the back room of a bar there. My guess is the game was allowed so long as the village got a cut. The village police would leave you alone as long as you didn't cause any trouble. The local TV news would launch an "investigation" into the area every year or so, but nothing ever changed. I recall one reporter asking the mayor onscreen, "How can you allow strip joints within blocks of your elementary school?" His response was, "Who do you think paid for that school?"

Anyway, this was a playground for me for the years I lived in that area. The strip joints were good, but the adult bookstores were great. What I would do is dress in lingerie under my street clothes and strip down once I got into a booth. There was one ABS that had booths with 8"x8" gloryholes in each wall, with sliding doors that latched to allow or deny contact. Both booths had to open their sliding door to allow access. It was especially good during summer, when I'd wear a t-shirt, shorts, and sandals with bra and panties underneath. They were always a matching set - an ass slut has to have some standards. When it was cold I'd add stockings under my jeans. Once I was down to lingerie, I'd select a good shemale movie and turn the sound up to hide the slurping noises. Then I'd unlatch and open the sliding doors on both sides about 1/3 of the way, leaving it up to the booth occupants on each side to decide whether to ignore, watch, or participate. I'd stand and watch the movie, caressing my lingerie-clad curves.

I'd watch through the gaps to see what the occupants of the other booths would do. If I didn't find a neighbor attractive for any reason, I'd close and latch that door, and wait until noises indicated that person had left. I found a number of attractive neighbors. Many times one of them would open their slide, then slide mine all the way open, and I'd find a nice cock waiting for me. I would stroke just about every one, and the better ones I would suck. The jackpot was finding one that would fit my ass perfectly - about 6", not too thick and not too thin. For these people, I carried condoms and a small bottle of lube. (This was the height of the AIDS epidemic, and I always required a rubber.) Once I brought one of these perfect specimens to hardness, I'd set the lube and condom on the ledge between the two doors, then pull my panties down and put my ass in reach. Now and then the guy would just back away and close their door, but a number took me up on my invitation. They would rubber up and lube up, and I would feel their hand or their cock poking at me. I would back up, bend over, spread my cheeks with my hands, and wait for insertion.

Oh, that moment when the head started to enter me....

Separated by a wall, I could control the insertion so I didn't get hurt, but it was so nice when I could just back right up to the wall and let my anonymous lover control things. It was so good, pushing past my rings, backing out a little, then deeper, then deeper, then deeper until I felt the tingle of pubic hair against my ass. The openings in the wall were large enough for complete contact. Then I'd just hold still and let them use me. Sometimes the door on the other side would open, and I'd have an audience. The booths were a little too wide for a short guy like me to reach the other side with my mouth, but I would stroke any rod that came through while I was getting a hard pole up my back door. It felt so good. I could brace my ass against the wall, get fucked, stroke my own meat, and stroke another man's cock. It wasn't unusual for me to come with my ass full, and my fucker almost always slammed into me as he filled his condom.

Even if I didn't get a second cock in my hand, the other side would often just watch, and having someone watch me get fucked with my panties down around my knees was a real turn-on. I could see the face through the door, sometimes they'd just show me their cock as they jerked to climax. One time, after the one in my ass finished and backed off behind a closed door, the guy on the other side struck up a conversation. "That was amazingly hot," he said, "But doesn't it hurt?" I laughed and said, "Practice, my boy, practice. Once you've done it a few times, the pain goes away and it just feels fantastic."

Other times the guy on the other side wanted my 7" cock after I'd been fucked, and I'd pull my panties up to just under my balls and slide it through to be sucked. It never took long for me to fill his mouth with my load.

It was just so great to feel that cock expand and shiver in my ass as the load was pumped into the condom. I usually only took one fucking per visit That was enough to get me off, and I usually was on a short schedule - I had a wife to get back to. There was a paper towel roll in each booth. I'd close both doors, clean up, stash my lingerie in a pocket, get dressed and go home. I didn't get the chance very often, but I enjoyed all of these encounters. I haven't bottomed now in a long time, and I miss it.

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I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

3 years ago
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Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

2 years ago
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Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

3 years ago
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Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

2 years ago
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Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

2 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

3 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

2 years ago
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Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

2 years ago
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Crossdressing Charlie Episode 3 Relinquishment

CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...

1 year ago
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Crossdressing Charlie Episode 4 Lust

CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...

3 years ago
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Crossdressing Charlie Episode 5 Rachels Date

CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...

3 years ago
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Crossdressing Charlie Episode 6 The Tennis Uniform

CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...

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