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Bookstore Crossdressing

"Giving Up My Butt-Cherry"

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It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out.

The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious big-titted MILF gobbling two huge cocks. My pants were off, the movie was on and my legs were on either side of the wall with my heels on and my cock in hand. After a moment of hearing footsteps outside I heard the door in the booth next to me open up and I saw a faint light come through the gloryhole.

After a moment, I heard a voice tell me how sexy I looked and to stand up so he can get a better look. I obliged and welcomed a hand on my ass. “Nice! You are so fucking hot,” said the voice in the other booth. Then he asked to see my cock. I’ve always considered my cock size average, but the compliments say otherwise. Just then the voice instructed me to unlock my door and we could share the movie. Feeling extremely horny I wasted no time at all.

The gentleman looked to be about in his mid 40s. There was plenty of room to sit but he took his place on the floor and asked if he could suck on my cock. I was glad to fulfill his request. I sat back on the chair in the booth and propped my legs up and positioned my heels against the wall. His ability to pleasure my cock had me panting and moaning like a slutty teen. I thought for sure we would get busted. I was certain we caught the attention of anyone else that may have been wandering around outside the booth. Making me drop my load, I had him stand so I could reciprocate and suck his cock.

Judging from his reaction, I was a natural. I sucked on that meaty bone until he could no longer hold back and he shot his load on my face, chest and stockings. Just then, a fresh stream of cum shot out of the gloryhole from the bystander in the next booth; all over my arm, stockings and heels. I had no idea we had an audience. But I was still hard and wanting so much more.

Back on his knees, my visitor continued to finish what he started. This time, with a finger in my ass from our neighbor in the next booth and my stud’s mouth on my cock, I was building up to what would be the most intense orgasm. When the time came, I warned him that I was going to cum, but he only sucked harder until I shot what seemed like a quart of hot jizz down his gullet. I thought for sure my kidneys would follow in the ejaculate. My head was swimming from the draining my balls had just taken.

When he finished, he zipped his pants and thanked me with a promise he would undoubtedly see me again. As he opened the booth, there were two more horny, older gentlemen peering in at me as I sat there with my cock hanging out, cum on my new stockings, smeared lipstick and jizm covered high heels. They had a smile on their face like two old geezers looking at a whore outside a village store.

I closed the door so I could regain my composure and clean up a little. I managed to always have wipes with me so I had to start from scratch with the lipstick if I wanted to continue on for the evening. I was spent, but still extremely horny. I was up for just about anything - twice. Sucking dick came naturally for me it seemed, and I learned to focus on the pleasure of others as well as my own.

The booth next to me opened and after a minute or so, a finger popped through the hole in the wall. I was still spent and needed a little more time to regain my erection, so I poked my finger back. Afterwards, a large cock-head peeked through the hole.

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I licked the tip in order to coax the rest of the member through, and soon a real man-sized monster was staring me in the face. I could see it pulsating in the faint light of the movie that was playing.

I feasted on this thing like it was my last meal. I knew it was one of the older gentlemen on the other side so I already had a face to go with the dick in my mouth. It was meaty and clean tasting. I was salivating at my horniness and soon my own cock was starting to come to life.

I stood for a minute to compose my stockings and I heard a faint thump on the door. It could only be the other man I saw in the hallway. At least I hoped it was an not the manager.

With what little was left of my lipstick on my face, I opened the door slightly to peer outside. The gentleman, with a rather handsome face and smile, asked if he could join me. I obliged and invited him in.

With a solid rock hard cock sticking through my wall, I returned to sucking it with gusto to show off my skills as a cocksucker and a male slut. My new visitor immediately had his cock out and was rubbing it against my face. I grabbed it with a free hand and jerked it for a while. I was so proud at how I could handle things like the woman in the video that happened to be playing.

I swapped back and forth between jerking and sucking. Using my tongue to massage the underside of the penis always does the job for older men it seems. After a few minutes, a stream of cum hit the upper part of my mouth and then the back of my throat. So much froth was emanating from my mouth that the man beside me started to chuckle. I managed to finish the job and then focus on the last cock.

I stood to straighten my stockings once more and show off my whorishness. It was then that the other gentleman sat in the chair and beckoned me to sit on his cock. I’ve had a finger or two up my bunghole, but never a cock, and a rather nice size cock at that. I shook my head and told him that I didn’t have any lube but I would be happy to suck him. No matter, he then turned me around and started to rim me for all he was worth.

That tongue was talented in every way. As he darted in and out of my bunghole, I was getting hard again. His thumbs worked my cheeks apart and his tongue explored deeper into my ass-crack. My head was spinning once again. Before I knew it, I felt the tip of a condom covered cock start to work it’s way into my sphincter. I was waiting for the pain to shoot through me as he took my ass cherry.

Before I knew it, I was even more heady and sitting on a meaty fuck-stick for the first time in my life. I was so proud of this moment. I started to writhe and move my hips like a gypsy whore. He lubed me up perfectly and it was turning out to be quite enjoyable. I thrust my hips a few times back and forth. Our moans were starting to get a little louder.

Someone was in the booth next to us and I could see eyes peering through the gloryhole. By now, my cock was throbbing again. My new stud had both of his hands on my hips fucking me, half standing, half sitting. This new experience took me to a whole new level of being a slut for older men.

Pre-cum was pouring out of my cock, and from the sound of my stud, he was grunting out a load as well. I couldn’t feel much in my ass but I knew there was a full condom ready to come out on a meat stick. He sat for a moment and waiting for his cock to soften up. I stood up and he slid out of what as left of my ‘man-pussy’. After about five minutes, I left the booth with my cum-soaked stockings on under my pants, my heels in my coat and smeared lipstick still on my baby face.

This was a new beginning for me in being a man-pleaser. I only looked forward to new adventures.

Published 
Written by Dinata
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