First Time
This is another in a long of line of true stories about my crossdressing experiences. This encounter happened back in the 90s.
It was Saturday night and I was on the road to the Queen Mary in Studio City. For those of you who were into the scene back then, you know what a happening place the Mary was. I was completely made up and was dressed in my favorite black, form-fitting dress. Underneath I had black panties and pantyhose. I had on great pair of 4 inch black hi heels. It was a long drive and just about 25 miles from my exit off the freeway, one of my tires had a blowout.
So here I was on the Ventura freeway pulling over to the side of the road. I got everything out to change the tire and had just begun loosening the lug nuts when a white van pulled up behind me. Two Hispanic guys got out of the van and approached me. I thought “fuck” I’m going to get ****d and/or killed. I was kneeling on the ground when one of the men asked if I needed any help. In my best girly voice, I told him no, that I was almost done. I had worn a long brown wig that night and it was really blowing in the wind. He said you sure? We would be happy to help you. I said thank you, but I got it handled. With that, they got back in their van and drove off.
Having dodged that bullet, I finished up and drove the remaining 20 minutes to the club. Entering the club I got a drink as fast as I could and related my experience to a couple of regulars I knew. I had a great time drinking and dancing with the other girls and a couple of guys. Towards the end of the night, the gurl that organized the parties at the Mary asked if I wanted to get a room with her and this guy named Roy. She said he really wants to be with you. I said sure. At this point in my life I had only been with a man a couple of times and never had anyone cum in my mouth. Well, that was going to change on this night.
We all left the club and hooked up at a nearby hotel. Once in the room we got down to business. I soon realized I was going to be the center of attention. Standing by the bed, Roy came up behind me, putting his arms around me and cupping my breasts and kissing my neck. OMG! That got me hot and hard in my panties. The other gurl who just call her ML got down on her knees in front of me. She slid her hands up my thighs under my dress. Reaching the waist band of my pantyhose she pulled the hose and my panties down to my ankles. My clitty was rock hard and staring her right in the face. She didn’t waste any time and started giving me head. Roy stopped kissing my neck and came around in front of me and gently pushed me onto the bed. With my cock still in ML’s mouth I lay back on the bed with Roy leaning down and kissing me. After a few minutes of hot kissing, I told Roy I really wanted him to face fuck me. He straddled my head and said open your mouth you little slut. I did as I was told and he shoved his beautiful cock all the way to the back of my throat. He reached down and grabbed my head in his hands and started fucking my face. I was licking the head every time he thrust into my mouth, loving the taste of his cock. A couple times he pulled his cock from my mouth and slapped my face with it. He asked, do like my cock fucking your face you little slut. I said oh God yes. Tell me what you are he said. I replied I am a cocksucker and I love cock.
All this time ML was still going down on me. I just kept my mouth open as Roy’s cock punished the back of my throat. He said you are a great cocksucker Jennifer. I want to cum in your mouth. Up till this night I had never had anyone come in my mouth. I had only sucked two cocks in my entire life. I said get on your back. With him on his back I got in a 69 position sliding my cock into his waiting mouth and dropping my cocksucking lips around his swollen cock. So as not to choke him to death I fucked his face with slow short strokes. I was bobbing up and down on his throbbing cock. ML came over and put her hand on my head and shoved my face down until my nose was buried in Roy’s pubic hair. She said suck his cum out you dirty slut. I started sucking really hard as my lips kept sliding up and down his cock.
It was getting really difficult to control my thrusts into Roy’s mouth and I heard him gag a couple of times. I felt his come filled balls and could tell he was getting close. I told myself to get every drop. He began thrusting up into my cocksucking mouth faster and faster. I was fucking his face just as hard. The moans coming for each of was really loud. Finally, I felt the first burst of semen into my mouth. OMG, that made me cum instantly. Every time another burst hit my tongue, my clitty would shoot into his mouth. After 5 or six shots, we were done. I had so much cum in my mouth that when I began to swallow it, some dripped down the corners of my mouth. ML came over and using her fingers, pushed the remaining cum into my mouth to swallow.
As I stated at the beginning of this story, this was the first but definitely not the last time that cum would shoot into this sissy faggot’s mouth.
It was Saturday night and I was on the road to the Queen Mary in Studio City. For those of you who were into the scene back then, you know what a happening place the Mary was. I was completely made up and was dressed in my favorite black, form-fitting dress. Underneath I had black panties and pantyhose. I had on great pair of 4 inch black hi heels. It was a long drive and just about 25 miles from my exit off the freeway, one of my tires had a blowout.
So here I was on the Ventura freeway pulling over to the side of the road. I got everything out to change the tire and had just begun loosening the lug nuts when a white van pulled up behind me. Two Hispanic guys got out of the van and approached me. I thought “fuck” I’m going to get ****d and/or killed. I was kneeling on the ground when one of the men asked if I needed any help. In my best girly voice, I told him no, that I was almost done. I had worn a long brown wig that night and it was really blowing in the wind. He said you sure? We would be happy to help you. I said thank you, but I got it handled. With that, they got back in their van and drove off.
Having dodged that bullet, I finished up and drove the remaining 20 minutes to the club. Entering the club I got a drink as fast as I could and related my experience to a couple of regulars I knew. I had a great time drinking and dancing with the other girls and a couple of guys. Towards the end of the night, the gurl that organized the parties at the Mary asked if I wanted to get a room with her and this guy named Roy. She said he really wants to be with you. I said sure. At this point in my life I had only been with a man a couple of times and never had anyone cum in my mouth. Well, that was going to change on this night.
We all left the club and hooked up at a nearby hotel. Once in the room we got down to business. I soon realized I was going to be the center of attention. Standing by the bed, Roy came up behind me, putting his arms around me and cupping my breasts and kissing my neck. OMG! That got me hot and hard in my panties. The other gurl who just call her ML got down on her knees in front of me. She slid her hands up my thighs under my dress. Reaching the waist band of my pantyhose she pulled the hose and my panties down to my ankles. My clitty was rock hard and staring her right in the face. She didn’t waste any time and started giving me head. Roy stopped kissing my neck and came around in front of me and gently pushed me onto the bed. With my cock still in ML’s mouth I lay back on the bed with Roy leaning down and kissing me. After a few minutes of hot kissing, I told Roy I really wanted him to face fuck me. He straddled my head and said open your mouth you little slut. I did as I was told and he shoved his beautiful cock all the way to the back of my throat. He reached down and grabbed my head in his hands and started fucking my face. I was licking the head every time he thrust into my mouth, loving the taste of his cock. A couple times he pulled his cock from my mouth and slapped my face with it. He asked, do like my cock fucking your face you little slut. I said oh God yes. Tell me what you are he said. I replied I am a cocksucker and I love cock.
All this time ML was still going down on me. I just kept my mouth open as Roy’s cock punished the back of my throat. He said you are a great cocksucker Jennifer. I want to cum in your mouth. Up till this night I had never had anyone come in my mouth. I had only sucked two cocks in my entire life. I said get on your back. With him on his back I got in a 69 position sliding my cock into his waiting mouth and dropping my cocksucking lips around his swollen cock. So as not to choke him to death I fucked his face with slow short strokes. I was bobbing up and down on his throbbing cock. ML came over and put her hand on my head and shoved my face down until my nose was buried in Roy’s pubic hair. She said suck his cum out you dirty slut. I started sucking really hard as my lips kept sliding up and down his cock.
It was getting really difficult to control my thrusts into Roy’s mouth and I heard him gag a couple of times. I felt his come filled balls and could tell he was getting close. I told myself to get every drop. He began thrusting up into my cocksucking mouth faster and faster. I was fucking his face just as hard. The moans coming for each of was really loud. Finally, I felt the first burst of semen into my mouth. OMG, that made me cum instantly. Every time another burst hit my tongue, my clitty would shoot into his mouth. After 5 or six shots, we were done. I had so much cum in my mouth that when I began to swallow it, some dripped down the corners of my mouth. ML came over and using her fingers, pushed the remaining cum into my mouth to swallow.
As I stated at the beginning of this story, this was the first but definitely not the last time that cum would shoot into this sissy faggot’s mouth.
1 year ago
