My first blowjob
I was 18 and had been crossdressing about 6 years. Mostly in my sister's stuff especially her prom dresses but I was slowly accumulating some female clothes of my own through trips to thrift stores. In those days I'd get incredibly nervous, heart racing, and walk around the store with my treasure until the line went down and I got the guts to purchase my girly things.
Mostly I would wear them at home and masturbate to guys and girls I went to school with. I really wanted to wear the cheerleading outfits, the gymnast leotards, and the heavenly formal dance dresses the hot girls wore. I still cherish the memory of the purple strapless dress I bought and wore that looked just like one Kim wore to ring dance. The more I dressed up and masturbated the more my mind wandered to going further, to playing the girl role in the bedroom, specifically to sucking a real hard cock and making it cum.
These gay urges got stronger every day and my orgasms to them more intense. I finally answered an ad from an older guy who also dressed up. You can't imagine how nervous and terrified, probably some of you gay sissies can, as I called him up and arranged to meet up at his place. My knees were trembling as I got out of the car and under my guy clothes were some little red silky panties with bows and a matching bra. I knocked on the door and an older gentleman answered. He was in a tight leotard and hose, my eyes immediately zeroed in on the bulge in his crotch.
Still shaking I went in and enthusiastically ripped off my shirt and jeans to expose myself in my lingerie. He laid on the bed and I crawled to him and started rubbing his cock underneath his leoatard. His moaning and the growing of his turgid shaft encouraged me and soon I freed up his penis from underneath the leotard and hose. Staring me in the face was another man's hard dick. My mind was flooded with thoughts of girls from school sucking off their boyfriends, sexy cheerleaders like Karen and Julie, and I wanted to be just like them. I kissed his hard penis then took the head inside my mouth. I was completely lost in the moment, any pretense of being a straight male was gone, and my body was in ecstasy being Brandi and being a cocksucker. My mind was flooded and my cock rock fucking hard in my silky panties as I bobbed up and down on his cockmeat. His moans encouraged me not to stop, and I didn't want to. I was lost in being a sissy cocksucker and it felt so electric.
Eventually he told me to stop and he instructed me to jack him off with baby oil. Seeing his hard cock throb and seeing him convulse as I stroked his beautiful penis slowly than faster, I knew I loved this so much. As he climaxed I fixared on the gorgeous stream of jizm that spurted out of his mushroom head onto his leotard.
Buzzed and dazed, I left. I don't think I even jacked myself off there and I had moments of disgust and guilt as I drove home. By the time I got home though I was unbelievably hard and horny and immediately went to my bedroom and masturbated in my panties three times in a row with some of the most intense orgasms I had ever felt in my young life.
I never saw the old man in the leotard again. I called him the next day from school begging to suck his dick in my "Kim" dress, the strapless purple formal dress, that I had stashed in the trunk of my car. He said he was busy and couldn't meet up and that was it. To this day I can't even tell you his name, but I can always sit back, close my eyes, and think about that first pretty taste of hard cock and that fountain of cum erupting out of his penis and tell you how glad and lucky I am to be a gay sissy cocksucker.
Happy cumming!
Branbran
Mostly I would wear them at home and masturbate to guys and girls I went to school with. I really wanted to wear the cheerleading outfits, the gymnast leotards, and the heavenly formal dance dresses the hot girls wore. I still cherish the memory of the purple strapless dress I bought and wore that looked just like one Kim wore to ring dance. The more I dressed up and masturbated the more my mind wandered to going further, to playing the girl role in the bedroom, specifically to sucking a real hard cock and making it cum.
These gay urges got stronger every day and my orgasms to them more intense. I finally answered an ad from an older guy who also dressed up. You can't imagine how nervous and terrified, probably some of you gay sissies can, as I called him up and arranged to meet up at his place. My knees were trembling as I got out of the car and under my guy clothes were some little red silky panties with bows and a matching bra. I knocked on the door and an older gentleman answered. He was in a tight leotard and hose, my eyes immediately zeroed in on the bulge in his crotch.
Still shaking I went in and enthusiastically ripped off my shirt and jeans to expose myself in my lingerie. He laid on the bed and I crawled to him and started rubbing his cock underneath his leoatard. His moaning and the growing of his turgid shaft encouraged me and soon I freed up his penis from underneath the leotard and hose. Staring me in the face was another man's hard dick. My mind was flooded with thoughts of girls from school sucking off their boyfriends, sexy cheerleaders like Karen and Julie, and I wanted to be just like them. I kissed his hard penis then took the head inside my mouth. I was completely lost in the moment, any pretense of being a straight male was gone, and my body was in ecstasy being Brandi and being a cocksucker. My mind was flooded and my cock rock fucking hard in my silky panties as I bobbed up and down on his cockmeat. His moans encouraged me not to stop, and I didn't want to. I was lost in being a sissy cocksucker and it felt so electric.
Eventually he told me to stop and he instructed me to jack him off with baby oil. Seeing his hard cock throb and seeing him convulse as I stroked his beautiful penis slowly than faster, I knew I loved this so much. As he climaxed I fixared on the gorgeous stream of jizm that spurted out of his mushroom head onto his leotard.
Buzzed and dazed, I left. I don't think I even jacked myself off there and I had moments of disgust and guilt as I drove home. By the time I got home though I was unbelievably hard and horny and immediately went to my bedroom and masturbated in my panties three times in a row with some of the most intense orgasms I had ever felt in my young life.
I never saw the old man in the leotard again. I called him the next day from school begging to suck his dick in my "Kim" dress, the strapless purple formal dress, that I had stashed in the trunk of my car. He said he was busy and couldn't meet up and that was it. To this day I can't even tell you his name, but I can always sit back, close my eyes, and think about that first pretty taste of hard cock and that fountain of cum erupting out of his penis and tell you how glad and lucky I am to be a gay sissy cocksucker.
Happy cumming!
Branbran
10 years ago