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Tail from the Road  

JerryNY01 65M  
2 posts
1/7/2022 9:35 am
Tail from the Road

I use to travel a lot for business. About 10 years ago I made the effort to set up dates using Senior Sizzle in various cities in the US where I would be visiting for work. I also hooked up with trannies from Bedpage. I was pretty successful . These are old stories but true ones.

Columbus, OH: My first.......I saw her pic in the transgender section of Bedpage. I spent many a time looking at the beautiful transgendered photos getting myself all hot and bothered. I finally acted on it when I got to Ohio. It was a late afternoon summer day when I reached out to her. She came to my hotel room that afternoon dressed in summer colors, a bright striped long lovely summer dress and a huge sombrero that flopped over her face and back of her neck. Her hair was short and bounced around her chin and neck. Her makeup was slight. Her face was smooth but definitely that of a young man in his 20s . We shared a glass of wine while she did all of the talking. Her story was sad. Her father abused her, her mother threw her out. She seemed flustered. Eventually I reached out to touch her. She immediately stood up and her dress fell to the ground revealing her satin green lingerie and crotchless stockings. I was a little taken back but very focused on her body. She pulled me off the couch, unbuttoned my pants and slid my shirt over my head. We landed on the bed and kissed for a very long time. She went down on me for a very long time. Unfortunately there have only been a few people who have made me cum by sucking my cock. I love getting sucked but I easily get over stimulated where my cock stays hard but I can't orgasm. Can be frustrating to my lovers at times. Jerking off or fucking a tight ass works for me. She eventually stopped and it was my turn. I had never sucked cock before but I was ready. I took my time and she knew I was working it out. After a while I told her I wanted her to cum in my mouth. She kneeled on the bed and jerked off and pulled my mouth to her cock just as she was cumming. She came in my mouth as I swallowed her small load. She kissed me, dressed and left me to think about my situation. /////////////////////////////

Pittsburg: i arranged blind date with a CD who dressed in public. We exchanged emails and then texts, and then chatting on the phone.She was very nice and very pretty. Our date was for the evening I was to fly in. She agreed to 9:00 PM at a place of her choosing. Unfortunately my flight was delayed. She had my flight # to track it so she knew I would be late. I called her just as I landed. She agreed to wait for me. Traffic sucked and I got to her around 10 PM. She was pleasant enough but clearly annoyed. We had a drink and then she decided to head out. It would have been a lot of fun.
White Plains, NY: I had been noticing a beautiful black CD in Bedpage. Eventually she became available near me in White Plains. I visited her in her hotel room on a Saturday afternoon. She answered the door dressed in a bight red bra, red garter with stockings and tall stiletto black heels. She was at least 6 feet tall. I followed her to the couch where she sat down and invited me to join her. We briefly chatted and then she stood up. That is when I first fell in love with her thick hard beautiful 8-9 inch cut cock. She waggled her cock in my face and had name follow her to the bed. She laid back and invited me to go down on her. I was up and down her shaft and all around her smooth huge balls. Her helmet barely fit in my mouth. She then moved me to my knees and fingered my ass with lubrication She started rubbing her condom covered helmet against my asshole and gently pushed it in to my ass. It took a while to work deep into me. With her first thrust I felt a pain deep inside me. I pulled away and lay on my side, I relaxed for a little bit and then she pulled me to my knees again. This time she only went in half way. She slowly started trusting while jerking me off. I had a huge orgasm and came all over the towel I was on. She fucked me for a long time after. I could see in the closet door mirror her tall gorgeous body thrusting and her thick cock sliding in and out splitting my body in half. I don't think she came. But I was exhausted and feeling wasted. I didn't realize when I reached out to her but I know now what she meant when she saiid she was a

Detroit, MI: I ordered room service off the bedpage transgender menu. A Little fat ugly guy in a dress came over. I turned him away......

Miami, FL: I found Mistress Lace and Bobbi in Senior Sizzle. Mistress Lace was an older female dom and Bobbi was her transgendered husband. The were very nice. They took their time with me, giving me an enema, showering me, and then putting me through their agenda of having me submit to them. Mistress Lace put a leash on me and guided me on my knees to a bedroom where she had me lick her heels and then her toes. She tied me to the bed and left me there for a while. It was really relaxing. I was just nodding off to sleep when she appeared naked and sat on my face and fucked my face until she came. She left me alone for a little while, then untied me and lead me to another room where she pulled me on to her table and tied me down with my legs suspended in the air by chains. My arms were bound to the table and my chest strapped. I was not going anywhere. Bobbi appeared and helped Mistress Lace strap on the biggest dildo I ever saw. Mistress Lace gave me the safe word and then proceeded to massage my ass with her fingers working lots of lube deep. She then stretched me slowly with increasingly larger dildos until I was ready to take it all. She flashed me a view of the big one and then leaned into me. I still remember the feeling of that huge dildo pressing hard against my ass until my ass stopped resisting no and a small shock of pain went through me as my ass relaxed and started taking the dildo. Bobbi started applying small vibrating eggs to my body just below my asshole and around the base of my cock. My body tensed up as Mistress pushed deeper. She paused and then started thrusting in and out as she went deeper. Once she was sliding in and out with no resistance she took over from Bobbi with the eggs and started moving the eggs all over my groin creating waves of energy pulsating through my groin. Bobbi focused on my lips with her mouth while Mistress Lace worked her magic. I had a huge orgasm that went on for minutes. As my cock became soft, cum was still oozing out of me. Bobbi sucked a lot of my cum off my stomach and deeply kissed me with it. When Mistress Lace was ready she pulled out of me and my body went limp. They unshackled me and guided me to the shower to clean up. My enema did not do a thorough job. It was a wonderful afternoon with two very loving people. I have tried to get back to them but they retired and moved away.////////////////////

White Plains, NY: I started regular fling with Roxxy Builder from Bedpage after my first 2 or 3 adventures with gurls. She became my teacher andI I became her student. We did everything we could imagine other then inviting a friend to join us. Roxxy was a very good teacher. She showed my how to open her up to take my cock. She patiently taught me how to suck cock and swallow cum. We often spent our time in 69 with her cock gaging me as she humped my mouth from above. . She was able to orally make me cum. She topped me on occasion. I got to see her transition using hormones to becoming a woman. She had me suck on her nipples to stimulate her breast development. She eventually could no longer get hard and cum. But her breasts filled out and here skin got so soft. She started spending more time in the City so I stopped seeing her. //////////////////

Plainview, NY: Mia from Bedpage is a beautiful Filipino trans with a beautiful body and a long thick dick. We would meet at her hotel room. She was always dressed in a short mini skirt and tight shirt. She did not like to kiss (understandable in her line of work). She could make me cum easily. She learned the hard way when we first did 69 and the minute she took me in her mouth I came. She was pissed. ////////////

Bethesda, MD: Charlie was from Senior Sizzle. She was from China and loved to dress in public. We would go to dinner and she was always so nicely dressed. She was a great conversationalist. Ultimately the conversation would go politics for which she was well studied (she worked in politics as a consultant). She would spend the night with me in my hotel room. She loved the attention I gave her. We would always be up late into the evening screwing each other. ////////////////////////

Houston, TX: Selena was my second trans and was from Bedpage. She was lively and liked be playful. Shows beautiful and had a very nice condo in a gated community. She was100% passable and lived full time as a woman. She did not enjoy<b> anal </font></b>sex. She had a tiny cock. It was the size of my thumb when hard and tiny balls. She would always sit me down, lift up her skirt, pull down her panties and feed me her cock. She would cum 30 seconds later with tiny amounts of cum. She could not get me off orally and she did not take it in the ass. It was a little frustrating for me at times.

13129 posts
1/7/2022 2:17 pm

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