Submissive Male Lessons
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How A Masculine Male Became A Submissive Bottom free porn video
I am currently 48 years old and my sexual encounters with transgender escorts, transgender girlfriends, crossdressers, and feminine looking and acting twink gay men began when I was thirty-one.
I am a masculine male, not what girls or guys would call very handsome of "hot", but I am attractive and never had a problem getting a girl to go out with me for the most part. Yes, I had more than my share of rejections but overall I did okay in the dating game. I am five feet eleven inches tall, weigh about one hundred and seventy pounds, light brown hair that was always cut in a professional short style, clean-shaven, and a while not overly hairy, I did have a nice masculine hairy chest. My butt was rather flat, a trait I shared with the men in my family. My best feature is my blue eyes that always got compliments.
I am masculine acting and looking and always liked to be in control when it came to sex, not the BDSM dominant type but I was a dominant lover for the most part. I am also a former Marine and spent six years in the Corps. I was married for five years but no children. I live in a mid-sized city in Georgia about seventy miles south of Atlanta.
My first gay or bi-sexual experience happened when I was thirty-one and living in Florida. I had been divorced for about four years and been living in the Orlando area for about six months. I moved to Florida for a job when I got a call from a career "headhunter" about a job in middle management. It was very similar to the job I currently had but the pay was a rather large increase than what I was making. Having no wife or kids and the only family I had was my mother and she was very independent and healthy and did not need taken care of and her parents, my grandparents, and they were also healthy and did not need to be taken care of so I took the job, bought a nice house in Florida, and moved.
For the past couple of years, before I moved to Florida, I had been having sexual thoughts of what it would be like to have sex with a male to female transgender. I never acted on it because I did not know how to meet a girl like that and the internet was rather new for people so there was no “cruising” online; then I moved to Florida and saw how different things were. One thing was you could go into an adult store and pick up these booklets that advertised escorts in each city; I got one. Transgender escorts were advertising with photos and I found one I thought was pretty, there were several who were pretty but this one caught my eye more than the others, and I made an appointment. I drove into the city of Orlando to her place, she was incall only and was very glad to see her photos were real.
Bella was of Hispanic descent, long black hair, as tall as I was, and had a great body and very pretty and looked to be in her twenties just like her ad read. She was wearing sexy lingerie. We settled the money, I paid for an hour for the GFE, and she took me to her bedroom. We kissed and she asked me to take off my clothes and we kissed some more as she stroked my hard cock slowly while I fondled her breasts and sucked her brown nipples. I rolled her to her back and pulled down her panties and her penis was hard. It was a little larger than mine which is average-sized, about seven inches long. Bella's was about seven and a half inches long and completely hairless on her penis. She was very feminine acting and looking. I then gave my first blow job. Naturally, I was not very good at it and gagged a lot but Bella was patient and told me what to do and I enjoyed it a great deal. We moved into a sixty-nine position with her on top and she started to suck my cock while I did her. I even started rimming her ass, something I enjoyed doing with girls, and she seemed to enjoy that.
After a while of us sucking each other and me rimming her, Bella said she wanted to get fucked. I moved her to her back and put on a condom while she lubricated her asshole and then put some on my penis and I entered her. I was no stranger to giving anal sex and my ex-wife loved to be fucked in her ass, but my excitement of sucking my first cock and being with a transgender got the better of me and I started to fuck Bella hard. She let me fuck her hard for a while and the pulled me down to her and started kissing me.
“Slow down, baby, we have plenty of time,” she whispered in my ear.
I slowed down and our sex became intimate, as intimate as one can be with a paid escort but Bella made it very nice and did give me the GFE. With the condom on I was lasting much longer than I would have without a condom and Bella asked me to get her off while I fucked her. I moved to kneel between her spread legs and saw her cock was hard and that excited me. Bella dribbled some lubricant on her erect penis and I started to jerk her off while I fucked her slowly. She was moaning and telling me how good it felt and soon she said she was going to cum. I started jerking her off faster and she let out a grunting moan and her cum exploded out of her cock and the site of it was incredibly erotic and I kept stroking her penis fast to milk as much cum out of her as I could. She giggled as she scooped up her thick, white cum and licked her fingers, and asked for me to stop because it was very sensitive now, and then she asked me to fuck her hard. I was more than happy to oblige.
I fucked this pretty Latino transgender with her legs on my shoulders and my cock ramming into her sweet, tight asshole and it was not long before I came. After my orgasm ended, Bella pulled me down to her again and started kissing me.
After I rolled off of her she told me if I wanted to do that again she was free for the next couple of hours. I knew that meant I would pay for it again, but I politely declined; not because of the money but because of the guilt and shame I started to feel. I never paid for sex before and then there was the shame of being a straight man who just sucked a cock and fucked a transgender. Even though Bella was pretty and feminine, in my mind at that time she was still a guy with a cock and I felt that stupid guilt straight men get after such an experience. Not being an asshole and a rather nice guy, I did not want her to know how I felt so I made up an excuse that I had to leave, got dressed, and left as Bella told me we should hook up again sometime.
When I got home I took a shower and felt like a pervert for what I had done and was ashamed of myself. My self-loathing lasted a few days but I could not get Bella out of my mind and masturbated several times over the next week thinking of what we had done. I soon started dating a girl named Tessa and all thoughts of what I had done with Bella left my mind because Tessa was several years younger than me, petite, very cute in an adorable girl next doorway, and sexually willing to do anything I wanted her to and we had a lot of sex some of it on the kinkier side.
My relationship with Tessa lasted about eight months and then I got bored with her. I cared for her but did not love her and she got very clingy and started talking about getting married. I was not ready to be married again.
After I ended things with Tessa, felt like an asshole because she was crying, I am a nice guy and hated to make her cry, I soon started having my sexual desire to be with another transgender. I did the escort thing again, felt guilty and ashamed afterward like I did with Bella, started fucking this one girl I met for a few of months in a mutual casual relationship to prove to myself I was a man and not gay then repeated the process with a transgender, but Tiffany was different than the other two escorts.
I met Tiffany online and was actually searching for a TG escort. The internet was taking off at this time but we still had dial-up and AOL was the go-to place for chat and all your internet needs. It was a Saturday afternoon and I went into a chat room for transgender girls looking to meet masculine men and I decided to chat. After about thirty to forty-five minutes of chatting and looking at profiles, Tiffany sent me a private message and told me she was a transgender living in Daytona Beach, about 30 a minute drive from where I lived. She was upfront and told me she was an escort and wanted to know if I wanted to meet for the afternoon. I asked for a photo and sent one of me.
She sent me a pic of her in a bikini and Tiffany was hot. She was so pretty and sexy. She had long thick dark brown hair, nice large breasts but not too large, and a thin body and a very pretty face. Being suspicious and actually thinking she was not a transgender because she looked so pretty and feminine, I asked if that was really her and she told me to wait a moment and about twenty minutes later she sent a new pic of her, yes it took that long back then to take a pic on a digital camera and upload it to the computer. She hid her face because she said she was not wearing makeup but I could tell by the body it was her and she was holding a piece of paper with that day's date and time written on it. I immediately asked her rate and asked if she offered GFE, I like kissing and foreplay, and I don't get into the "just meet and fuck" too much. She replied yes that she offered GFE and a lot fo other things and gave me her rate which was very reasonable and less than the other TG’s I had been with. I told her I would love to meet her and she said give her about an hour and a half to get ready and gave me directions to her place. She asked me if she should wear anything special and I asked if she had a schoolgirl outfit. Tiffany replied she would see what she can come up with.
I waited as long as I could and was extremely horny and being impatient I left earlier than I needed to and arrived at her apartment early. I knocked and was let in by a young man who was obviously gay and he told me to have a seat and that Tiffany was still getting ready. In the room were 2 other people, another gay young man and a girl that kept a pillow over her face. I found out later she was also transgender and was not wearing any makeup and did not want me to see her face without makeup, but she had a great body and I kept stealing glances at her tan, shapely legs sticking out of the short blue shorts she wore. They basically ignored me and the two gay men played on the computer and were chatting on AOL. I felt awkward. Here I was, sitting and waiting for a TG escort in front of her friends and roommate. Made me feel like a pervert.
I waited about fifteen minutes before Tiffany came to collect me and she looked hot and just like her photo. She was wearing a very short black micro mini skirt that was pleated and flared out at the hem and a white button-down shirt she had tied up to make it so her belly was bare and I could see the red bra through the material. Her long hair was in two ponytails. She looked sexy and stunning. She led me to her bedroom, locked the door, and turned on some music, and set the volume on low.
"I am sorry I don't have a schoolgirl outfit, this is the best I could come up with," she told me as we settled the payment for her time and she smiled.
I told her she looked very beautiful and she did and she blushed and said think you. Tiffany laid me on the bed and then lay next to me and we started kissing. There was just something about her that made me want her so bad. Not just her looks but as a connection and I knew it was stupid. You don't have connections with girls you pay to have sex with, but I could not help it. We kissed and touched one another and I exposed her breasts, which, naturally since they were implants, firm, perfectly round, quarter-sized areolas, and tipped with pink nipples that were already erect, puffy, and longer than others I have seen on girls. Her body was lightly tanned and she had tan lines around her breasts and I found that sexy, I always liked tan lines on a girl. As we lay side by side kissing, I started to unzip her skirt and she pulled it down and I rolled her over on her back and slipped my hand in the waistband of her panties.
"This is what I wanted to see," I told her and started to pull her panties down.
Tiffiny stopped me and seemed embarrassed, “I…I am not very big,” she told me.
“I don’t care, neither am I. I am average," I assured her and removed her panties.
When we were kissing I could not feel her penis against me and assumed she was not hard. The second transgender girl I had been with could not get hard because she told me she just had her hormone shot the previous day and I thought maybe that was the same with Tiffany. When I took off her panties I saw I was wrong, she was very erect and the reason I could not feel her cock was that she was indeed small. She could not have been more than five inches long, not much girth to it, her testicles were also small and scrotum was taut, and of course completely hairless. I liked it a lot and told her it was very sexy right before I took it in my mouth. I really did like how her penis looked a great deal.
I enjoyed giving blow jobs, up until I had my own orgasm at least and then I started to feel ashamed, and I was especially enjoying sucking Tiffany's cock. She must have liked it also because she kept calling my name and telling me how good it felt. I could not seem to get enough of sucking it, licking it, and since it was not as long as Bella's cock I was able to deep throat it. Soon Tiffany told me she was going to cum, and I was surprised she was going to orgasm that quickly, and I kept sucking her harder and faster and used my hand on her now slick shaft.
Before we met and were chatting online we discussed some things we liked and did not like or do and one of mine was I will give oral sex but no cumming in my mouth. Remembering that, Tiffany warned me again she was going to cum, but I did not stop. I wanted her to cum in my mouth and she did. He cum was not thick, but thin and clear looking (hormones I assumed), but I swallowed it and then licked her softening cock after. It tasted good and I liked it a lot.
“Fuck, Sean, that was great," Tiffany told me as she caught her breath. "I came so fast. I normally don't cum that fast with a client."
I smiled up at her, "I enjoyed it myself." Playing along with her game of acting like she never came that quickly with a client. I knew I was a "trick" for her but thought it was sweet for her to lie to me.
She ran her hand through my hair very seductively, “I thought you didn’t swallow?”
I moved up to lay next to her and started kissing her, my own cock was rock hard, "I never have before but for some reason, I wanted to with you," I whispered in her ear as I kissed her neck.
“My turn now. I love sucking cock," she told me and had me lay on my back and moved her body down to my side and started to give me a blow job.
It was great! She sure knew how to suck a cock. I know how it is, that one gets a great blow job and said, "it's the best I ever had," and then a week later he gets another one and says the same thing; but with Tiffany, her blow jobs were the best I ever had and years later I would still same the same thing. I don't know what she did differently or of she did anything different, but she sure knew how to suck cock.
After several minutes I told her to put her ass in my face because I wanted to rim her sexy hole and we started to sixty-nine. She got hard again as I rimmed her tight hole, which was so sexy looking, and I sucked her cock while also; going back and forth from her small penis to her tight asshole, even fingering it at times. After some long delightful oral play, she told me she needed me to fuck her. It always took me a very long time to orgasm from a blow job. Not being a braggart about it, but it just did. Some guys can cum quicker with oral sex than intercourse, some guys can orgasm quicker when fucking a girl from behind as opposed to missionary position, and for me, it took longer to make me cum with oral sex.
“Did you bring a condom?” she asked as she sat on top of me, reaching around and stroking my hard cock as I played with her nipples. “I don’t have any.”
Fuck! I did not even think about that and the other transgender girls I was with I asked if I needed to bring some and or lubricant.
"Damn, no," I told her and she frowned.
“Well…. I don’t have STDs, do you?” she asked.
"No, I am clean."
She smiled, "You can bareback me if you want. I am very selective of my clients and you are the first new client I have seen in almost a year."
I took the risk and believed her and told her I would like that. She did have lubricant and lubed her own asshole and then my cock and while still on top of me guided it into her tight hole and slowly lowered herself on me. Tiffany rode my cock nice and slow and ground her hips for a while and then bent down and kissed me as she moved her nice small ass up and down on my cock. I soon rolled her over onto her back and started to fuck her. I went nice and slow at first until she started begging me to go harder and fuck her. I was more than happy to. Her asshole was so tight and seemed to suck my cock into her.
I fucked Tiffany hard and slammed my cock deep into her wonderful asshole as she clenched my back. I kissed her lips, her neck, and her pink hard nipples as I fucked her and enjoyed listening to her moan and whimper and cry out to God in pleasure as the bed squeaked loudly. I was sure the three people in the apartment heard us, apartment walls are rather thin, but we did not care. I also wanted it to last as well; I did not want to cum so soon and I wanted to enjoy this lovely transgender girl's body as long as I could.
"Ohhhh fuck....ohhh my God!" Tiffany screamed out when I drove my cock deep into her and held it there. "Ohhh, baby, you are so deep in my ass. UHHH my God...that....that...ohhh God, keep doing that, Sean."
She begged me when my penis was buried deep in her ass and I started rotating my hips and pushing my cock into her ass as deep as far as it would go. I would then fuck her hard again for a while and then repeat the process of pushing as deep as I could into her and rotate my hips and then fuck her hard as I kept kissing as much as her body as I could. I fucked her like that for several more minutes and then I pushed deep into her again and I told her I was going to cum soon.
“Yes…ohhh fuck, baby, you feel so good…cum in my mouth…please, Sean, cum in my mouth," Tiffany begged me.
When I was about to cum I pulled out of her, straddled her chest, and she lifted her head up and took my cock into her mouth and stroked my shaft rapidly and I let out a masculine grunt when my penis exploded in her mouth. Tiffany swallowed all of it and kept milking it for more. It was incredible.
When Tiffany could not coax any more cum from my dick I rolled off of her and lat on my side facing her and we started kissing again. I did not feel that normal guilt or shame about what I had done as I did in the past and instead I wanted to stay with her as we pressed our naked bodies against one another.
"Can I cum now?" she asked me. I liked how she asked permission to do things like when she asked permission to give me a blow job and to fuck her, and now if she could cum.
I grinned, "I want to help," I told her.
I moved Tiffany to her back and started sucking her cock again and once again she came in my mouth.
I was hard once more and wanted to fuck her again, but we had engaged in a lot of foreplay and kissing before we started having sex and I know my hour was up.
“I want to fuck you again. I have more cash,” I told her.
Tiffany smiled, “You don’t need to pay me. I am free all day.”
I fucked her from behind that time and when I was going to cum she begged me to cum in her ass, which I was more than happy to do. Even after the second time, I fucked her I still wanted more. I was enthralled by Tiffany for some reason. We spent the next two hours in her room talking as we cuddled, kissing, touching one another, sucking one another's cocks, and fucking two more times. Eventually, I did have to leave and told her so.
“We need to see each other again. Go on a date next time.” She told me as she lay in bed and watched me get dressed.
“Sure, I would really like that. Maybe you could come to my house and spend the night. Just let me know how much." I told her.
Tiffiny sighed, “Wow, you are totally clueless aren’t you?” she asked sounding a little upset.
“What?”
“I meant a real date like two people who like each other go on; not you as my client. We fucked the first time as you being my client but the rest of the day I did because I wanted to and I like you.”
I was very surprised and felt stupid for being so clueless and told her I was sorry and I would love to go on a real date with her. She said good and told me what nights she was free and was not seeing any of her clients and we agreed on a date within the next week. I walked to the bed and leaned down and kissed her and she pulled me tight to her and kissed me back with passion.
"Let me get dressed and I will walk you out," Tiffany told me.
She slipped on a tee-shirt and a pair of blue jean cutoffs and walked me out of the room and to the door. The two gay young men were gone, but her roommate, Crystal, was still there and she had put on makeup by then so I got to see her face. She was cute.
Tiffany kissed me quickly on the lips, "I am looking forward to our date," she told me.
"Me too," I said sincerely.
"Just so you know I don't put out on the first date." She giggled as she opened the door to her apartment.
As the door closed behind me I heard Cyrstal say, "Sounded like someone had a good time."
I drove home and felt no shame or guilt as I had done in the past and was thinking of how I was looking forward to going on a date with the pretty transgender girl. When I got home I did not take my normal shower to wash the shame off of me but instead enjoyed the scent of Tiffany on my body.
Emely
- 11.05.2021
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- Trans
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