My first time with another man was when I was 18 back in the late 80’s. My girlfriend was a virgin and the farthest we went was kissing and rubbing together with our clothes on.
I would take my dirty magazines out behind where we lived in the woods and take off all my clothes and masturbate. I was out there every day there was nice weather masturbating and cumming on myself. I would sit nude on a log and stroke myself until I would cum on my stomach and then I would lick the cum off my fingers wishing it was my girlfriend doing it. I heard a branch break and turned around to see Josh, our neighbor’s son home from college.
He laughed and told me to grab my clothes and I better come with him or he would tell everyone including my girlfriend what he saw. I put on my clothes and we walked down to his parent’s house and went inside. He then told me that since I must like cum that that he wanted me to shut all of the blinds and then suck him off. He was a geek who never really had a girlfriend.
I said no way but he reminded me of what he saw and he could ruin my relationship with Marissa before I ever got to fuck her. He left for a minute and then came back and handed me a wig. I said what is this for and he told me that he wasn’t gay and was going to be sucked by a woman. He peeled off his clothes pushed me down on my knees.
I touched him tentatively and felt him harden. I started to stroke as he pushed my head down. I started sucking, very awkward at first. He had a 7 1/2″ cock and I started down further and further with the help of his hand pushing on my head. It wasn’t but 2 minutes and he blew a huge load of cum in mouth and I gagged. He told me I had to swallow it all and lick him clean. I did and then got dressed. He told me thanks as I walked out.
I thought that was all until he called 2 days later and told me to come over. I arrived and he had a dress in his hand and nylons. He had me strip off my clothes and put on the nylons, dress and wig. The dress was his Mom’s and luckily I was really skinny but it was still tight. I came out and he put lipstick on me and then he kissed me with his tongue. He then took Polaroid’s of me. I tried to push him away but he held me tight. It was weird but I got hard while kissing him. He was naked and pushed me down on my knees. I started sucking but he told me he wanted it slow this time. I took my time licking him, licking his balls and then he told me to lick his ass. I had given up resisting anything at this point and licked his asshole. He then pushed my head towards his cock and I worked up and down without his hand this time and after about 15 minutes he filled my mouth with another huge load of cum. I swallowed it all and licked him clean. He then pulled me up to kiss him calling me his bitch.
3 days later I went back to his house. He once again had me put on a dress, nylons and a wig. He had me down on my knees sucking his cock and licking his balls when someone else walked in. It was a friend of his named Greg whom he invited over for some fun. Greg stripped and I was soon sucking back and forth between them. I was on my knees sucking Josh when I felt Greg behind me. He ripped a hole in the nylons and I felt a slimy Vaseline covered finger probe my hole. I tried to pull away but Josh kept my head down while Greg inserted his cock in my virgin ass. It really hurt at first but after he got all the way in and started moving in and out, I loved it. As Greg started fucking me Josh pulled away and took some Polaroid’s. After what seemed like an hour Greg pulled out and came all over my face. I was so sore and turned on that I didn’t pay attention when he shoved his cock into my mouth to lick clean.
I then felt Josh behind me and his cock penetrated easily. He fucked me like there was no tomorrow and after just a couple of minutes filled my ass with his cum. He then asked Greg what he thought of his little whore. Greg laughed and said he can’t wait for more. Just then Greg put his hardening cock back in my mouth and I licked his ass, balls and deep throated him until I swallowed his cum.
This went on for a couple of weeks. Sometimes just Josh and sometimes both of them. One day they had me shave my balls, cock underarms and legs smooth. Most of the rest of my body was fairly smooth. One other time they let me cum on the coffee table but I had to lick it all up while they took a few more pictures. I was told to keep it like that or my pictures would be all over the school and neighborhood.
On a Saturday I showed up and Josh had me shower. Then I get out and there is Greg’s sister. Jane is a bigger girl but still fairly attractive. She was talked into helping them make me a sissy. Although they didn’t tell her why except that it was a prank. She shaved me all over, taped my cock down and had me put on some panties, a padded bra, a mini skirt and a blouse. She then helped me put on the wig and expertly applied makeup. I really looked like a fairly sexy woman. She left after they gave her some alcohol to pay her off.
I then had my picture taken by Greg and Josh before I was told to suck them off. I was helping them get out alcohol and mixer and soon people started showing up. It was a bunch of guys (7 in all) and I was to be their entertainment. They all were told who I was and that I was their girl for the night. They had me give them dances, I was kissing each of them and feeling them get hard. After they all had several drinks, they started undressing. I couldn’t believe how exciting it was to be their girl. After they were each undressed, I took turns sucking on each of them. It was so much fun being able to play with 7 different cocks that were all different sizes. Nobody was huge but there was a guy who was 7″ and thick as a beer can. As I was sucking on 2 guys I felt the mini skirt being lifted and my panties were pulled to one side. I felt the lube worked into my ass and then a cock about 6″ being pushed in. He pounded away at my ass for 15 minutes while I sucked 3 or 4 guys. One guy came on my face while the guy in my ass pulled out and came on my face and in my mouth. Over the course of that drunken evening each of them came twice and some 3 times. I had 5 or 6 loads in my ass and the rest was on my face or in my mouth.