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I had a few girlfriends in HS but my real attraction has always been towards other guys. The first time I masturbated, I was thinking about my older sisters boyfriend. When I was 16 my sister confronted me about her missing panties, bras and other clothes. She was the first to know I liked guys and she kept my secret. My first time with a guy was when I was 19. I spent the night drinking some beers at a friends house and came home around 10pm with a very nice buzz. I was tired of thinking about guys and wanted to actually hook up with one. I decided to call one of those phone hook-up dating services and talk to some guys.
The very first guy I talked to was Eddie. He was in his 50's and was a nice guy. He wanted to meet up. He said he would go as slow as I wanted without any pressure. It sounded good so I gave him my address and told him to come pick me up. He picked me up about 30 minutes later. He was an older man with a better than average body. I was attracted to him immediately. We drove around and started talking before we stopped at a beach park. One thing led to another and we were taking turns stroking each others dicks. Before I know it, his cock was in my mouth and I was getting my first taste of cock. I was immediately addicted. He dropped me off after that but we made plans for the next evening/night.
I got to his apartment around 4pm the next day. It was a small apartment with a bed, and massage table in the main room, with one bedroom to the side. He was a masseuse. He gave male on male full body messages for a living. We went inside, he got us a beer and we sat on his bed. Straight, gay or tranny porn, he asked. Gay I said. He popped in a movie and we sat back. After about 2 minutes I gave in. "Eddie, will you please fuck me tonight?" "I was hoping you would ask me that." We quickly undressed and then he started kissing me and playing with my dick and my ass. He laid me on my stomach, lifted my ass in the air and started finger fucking me. It felt incredible. I was tingling and shivering from pleasure. Just when I thought I couldn't feel any better, he put the tip of his cock inside my ass and slowly pushed deeper inside me. I had never felt such a feeling, it was better than I could ever imagine.
I remember moaning and screaming with my head in the pillow. I remember telling him I loved him and his dick. I told him that he can fuck me anytime he wants. After 15 minutes, I could feel his dick getting bigger. "Im going to cum" he said, as my moaning started getting more intense. He started fucking me harder and harder until he pulled out and shot his cum all over my ass. I didn't move. I just laid there, shivering and quaking, staring at this naked man and his beautiful cock.
After I gained some energy, we started talking about fantasies. He told me he likes fem-boys. He likes crossdressing, submissive sissies. He likes being the sugar daddy and spoiling his girls with clothes and sex. I already liked crossdressing so and older guys. It was a nice match. I was still naked, with my head on his naked chest when he told me he had a massage appt in almost an hour and that I could go into the bedroom till he was finished, or stay on his bed if it was okay with his client. The client was okay with me watching the massage from the bed.
When the massage was over, Eddie walked his client downstairs. When he came back, he told me the client would pay twice as much if I helped with the massage. He said he had a few massages scheduled for the next day, including an early morning one. Would I be interested in helping with the massages, maybe even giving hand jobs and/or blow jobs. I eagerly said yes. With my new cock addiction, the thought of it was so exciting. He fucked me one more time then we went to sleep. When I woke up, Eddie said his client was almost there. He suggested I stay naked because the client would be more likely to get the upgraded massage.
I have no experience giving massages but Eddies client didn't seem to care. He was laying on the table, with a rock hard dick before I started. After about 2 minutes he asked Eddie how much for everything as he was staring at me like I was a cheap slut. I will never forget how awesome it felt knowing this guy saw me as a nice piece of ass and that he would pay to spread my legs open and get inside of me. I was brimming with confidence. After they settled on the price, I immediately started rubbing the clients cock, eventually kissing and sucking it. I was brimming with confidence and ready to let this complete stranger have his way with me. I grabbed his hand and suggested we move to the bed as I started leading him in that direction. After I worshipped his cock for a few minutes, he put me on all 4s and fucked me from behind. Eddie watched from his massage table. His client came real fast but it was still very hot. When he was done, he paid Eddie then slipped me an extra 20 before he left. He even wrote his phone number down on the 20 before giving it to me.
When he left, Eddie told me we had a few hours before his next client and suggested I nap and shower because I slept little the night before. I woke up to Eddie giving me a bag of clothes. "My next client likes sissies so you might want to be in panties when he gets here. When his client arrived, I was wearing a little school girl outfit. Red, and black checkered skirt, I small white top with pink panties and a pink bra underneath. We took him to the massage table and got him undressed. Before I could start massaging him, he already had one hand up my skirt. We decided to skip the massage and go straight to the bed. This client fucked me the whole hour. When his time was up, he paid for another hour because he wasn't finished with my ass. After he paid Eddie, I got another tip, and another phone number.
I knew I liked guys at an early age but I never knew I would fall in love with cock this much. I never expected to turn into a sissy whore but I wouldn't change a thing even if I could, except I would have started getting fucked earlier in life.
The very first guy I talked to was Eddie. He was in his 50's and was a nice guy. He wanted to meet up. He said he would go as slow as I wanted without any pressure. It sounded good so I gave him my address and told him to come pick me up. He picked me up about 30 minutes later. He was an older man with a better than average body. I was attracted to him immediately. We drove around and started talking before we stopped at a beach park. One thing led to another and we were taking turns stroking each others dicks. Before I know it, his cock was in my mouth and I was getting my first taste of cock. I was immediately addicted. He dropped me off after that but we made plans for the next evening/night.
I got to his apartment around 4pm the next day. It was a small apartment with a bed, and massage table in the main room, with one bedroom to the side. He was a masseuse. He gave male on male full body messages for a living. We went inside, he got us a beer and we sat on his bed. Straight, gay or tranny porn, he asked. Gay I said. He popped in a movie and we sat back. After about 2 minutes I gave in. "Eddie, will you please fuck me tonight?" "I was hoping you would ask me that." We quickly undressed and then he started kissing me and playing with my dick and my ass. He laid me on my stomach, lifted my ass in the air and started finger fucking me. It felt incredible. I was tingling and shivering from pleasure. Just when I thought I couldn't feel any better, he put the tip of his cock inside my ass and slowly pushed deeper inside me. I had never felt such a feeling, it was better than I could ever imagine.
I remember moaning and screaming with my head in the pillow. I remember telling him I loved him and his dick. I told him that he can fuck me anytime he wants. After 15 minutes, I could feel his dick getting bigger. "Im going to cum" he said, as my moaning started getting more intense. He started fucking me harder and harder until he pulled out and shot his cum all over my ass. I didn't move. I just laid there, shivering and quaking, staring at this naked man and his beautiful cock.
After I gained some energy, we started talking about fantasies. He told me he likes fem-boys. He likes crossdressing, submissive sissies. He likes being the sugar daddy and spoiling his girls with clothes and sex. I already liked crossdressing so and older guys. It was a nice match. I was still naked, with my head on his naked chest when he told me he had a massage appt in almost an hour and that I could go into the bedroom till he was finished, or stay on his bed if it was okay with his client. The client was okay with me watching the massage from the bed.
When the massage was over, Eddie walked his client downstairs. When he came back, he told me the client would pay twice as much if I helped with the massage. He said he had a few massages scheduled for the next day, including an early morning one. Would I be interested in helping with the massages, maybe even giving hand jobs and/or blow jobs. I eagerly said yes. With my new cock addiction, the thought of it was so exciting. He fucked me one more time then we went to sleep. When I woke up, Eddie said his client was almost there. He suggested I stay naked because the client would be more likely to get the upgraded massage.
I have no experience giving massages but Eddies client didn't seem to care. He was laying on the table, with a rock hard dick before I started. After about 2 minutes he asked Eddie how much for everything as he was staring at me like I was a cheap slut. I will never forget how awesome it felt knowing this guy saw me as a nice piece of ass and that he would pay to spread my legs open and get inside of me. I was brimming with confidence. After they settled on the price, I immediately started rubbing the clients cock, eventually kissing and sucking it. I was brimming with confidence and ready to let this complete stranger have his way with me. I grabbed his hand and suggested we move to the bed as I started leading him in that direction. After I worshipped his cock for a few minutes, he put me on all 4s and fucked me from behind. Eddie watched from his massage table. His client came real fast but it was still very hot. When he was done, he paid Eddie then slipped me an extra 20 before he left. He even wrote his phone number down on the 20 before giving it to me.
When he left, Eddie told me we had a few hours before his next client and suggested I nap and shower because I slept little the night before. I woke up to Eddie giving me a bag of clothes. "My next client likes sissies so you might want to be in panties when he gets here. When his client arrived, I was wearing a little school girl outfit. Red, and black checkered skirt, I small white top with pink panties and a pink bra underneath. We took him to the massage table and got him undressed. Before I could start massaging him, he already had one hand up my skirt. We decided to skip the massage and go straight to the bed. This client fucked me the whole hour. When his time was up, he paid for another hour because he wasn't finished with my ass. After he paid Eddie, I got another tip, and another phone number.
I knew I liked guys at an early age but I never knew I would fall in love with cock this much. I never expected to turn into a sissy whore but I wouldn't change a thing even if I could, except I would have started getting fucked earlier in life.
Myra
- 12.05.2020
- 6
- 0
