Teen is Forced to Crossdressbyfun4all6969©
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.
The last part of the entertainment of the night was for me to put my cock over my mouth and try to suck it. I am very flexible and was able to get 2 inches of my 7" cock into my mouth. I kept sucking for only about a minute before I filled my mouth with a 2 week load of cum. They all cheered as I licked it all up. As the night ended and they all left, I was completely exhausted and felt very used. Greg pulled me up to show me the collection of Polaroid's they had of me during the course of the night. He told me they wanted to make sure I continued to take care of all of their friends at the upcoming parties they planned.
Through all of this, I still managed to keep my relationship with my hot girlfriend Marissa. I was getting further with her each time and the night after my gang bang I was able to get my hand down her pants and into her pussy. I also was able to lick and suck her perky little breasts. I was in heaven and I knew soon I would be getting further. She even squeezed my cock through my pants a couple of times and she remarked that she may consider giving me a hand job on the next date.
Later that week I was out with her again and she gave me the hand job after hours of petting and kissing. Oh my, I was so turned on. It only took a couple of minutes of stroking and I shot a huge load up my stomach and onto my pulled up shirt. She was very shocked as this was the first time she had ever seen a guy cum. Afterwards, I fingered her until she had her own orgasm and then we kissed goodnight.
The next day I was due at Greg's house for another party. I loved the excitement of the party but felt very guilty afterwards. I was wishing they would go back to school and leave me to have fun with Marissa. Even as I thought that, I was pained to think of no longer being fucked and eating their cum.
I showed up at Greg's and as his sister, Jane was getting me ready for my second gang bang. I commented to her about how great things were going with Marissa. She said that she was happy for me but what would happen if she would find out my whoring ways. I froze and begged her not to tell and she didn't say anything. I asked how she knew what I was doing here and she said her brother told her.
I walked out after getting dressed up and there were 10 guys there. Jane walked out and sat next to the guys. She was there to watch and help keep and get the guys hard to fuck me. I was immediately bent over the couch and Jane was told to lube up my ass. From that point on, I don't remember much other than the guys just were always there. One in my ass and one in my mouth. It felt like it lasted for 24 hours but it was really 6. Every guy fucked me in the ass and mouth 3 times or more. Some came on me, some in my mouth and some in my ass. I looked over several times to see Jane sucking a guy hard again so he could come over a fuck me again. They were all different sizes and flavors. There were 2 Asians, 1 Black, 2 Hispanic and the rest white. There were cocks from about 5 inches to 9 inches.
There was one guy who was about 7" and he could fuck for 20+ minutes each time and then the 9" guy only lasted about a minute. I know that the 5" guy tried to fuck me after an 8" and thick guy and he gave up and put it in my mouth because my ass was stretched wide. I came 3 times myself, twice on the floor and once on my stomach without touching myself. Each time Jane made sure that I cleaned it up with my tongue. In the early evening the outing was over and I showered and dressed to go home and Jane told me that I better always do what she wants or she will tell Marissa.
About 2 weeks went by without hearing from Jane but I had been over to pleasure Josh and Greg and a couple of friends just about every other day. I had actually got to lick Marissa to orgasm about 2 days after the last party and she had masturbated me to a big cum on my stomach. It was very tempting to lick it up but I stopped myself before my fingers got to my mouth.
Jane called me up on a Thursday and asked for me to come over to Greg's house. I went over and she was the only one there. She told me that it was time for me to earn her being quiet. She had 4 friends coming over and she had told them about me and my girly slutty ways. One of her friends was bringing over a dildo she found in the back of her Mom's closet. I protested but she said she would tell Marissa the minute I left and she had some great pictures to share.
I quickly agreed and she dressed me as her slutty friend. Her 4 friends showed up and they brought alcohol. I served them for an hour or so until they loosened up enough to order me around. 2 of the girls were from our school. They had me dance for them and strip down. I was hard and one girl kicked me in the balls. My cock softened as all of them laughed. I was bent over and each girl took a turn with the 8" hard vibrator that they had. They fucked my ass hard and it hurt more than any guy because it didn't bend at all.
They each kept drinking, verbally abusing me and fucking my ass until Greg showed up. Jane wanted Greg to fuck me and have me eat his cum for the girls. Greg undressed and let each of the girls touch him and then he proceeds to fuck me for a good 15 minutes. All the while the girls are gasping and cheering him on. He pulls out and puts his cock in my mouth. The girls can't believe I just took a cock that was in my ass right into my mouth. He pulls out and cums on my face and into my open mouth. I eat it for all the girls to see. As the girls were getting up to leave, they each took turns coming over and kicking me in the balls with their bare feet. I lay on the ground naked for 30 minutes before I could walk.
A week later Jane calls as I am leaving for a date. This is not just any date but one where I know I will get lucky. She wants me to come over and be the entertainment for her 4 friends and 3 new ones. I tell her no way because I have a date and she tells me this will be my last date with Marissa if I don't come over. I am scared but so much want to have sex with a woman.
Marissa and I go to her house because her parents are gone for the night. We both kiss and grope for an hour on her couch. I nibble and touch everywhere on her perfect body. I even lick her asshole and she almost cums on the spot. We then head up to her room. We kiss, I fondle and kiss her breasts and then lick her to orgasm. She sucks on me briefly and even kisses me with her juices on my face. She tells me that she wants me inside her and I ask whether I should go get my condoms. She said that she just got on the pill a month before because she was waiting for this night and she wants me to orgasm inside her. I put my cock inside her and realized I wasn't going to last long. We started moving together and she was moaning and within 2 minutes I was grunting and filling her with my cum. I felt so bad for not lasting longer on her first time that I dove between her legs after my soft cock slipped from her pussy. She tried to stop but I insisted. I licked her to another orgasm as I cleaned my cum from her pussy.
By this time, I am hard again and I push back inside for a 5 or 6 minutes session before I cum again. We collapse together until morning. In the morning I am hard and she feels my cock against her. We start kissing and I nibble my way down her body. I stop to suck on both of her breasts before continuing down her stomach to her wet pussy. I lick her to orgasm and then she tells me she wants me inside her. I push in slowly and she moans. We move back and forth together until I cum deep inside for a third time.
3 days later I get a phone call to meet at Greg's house for a day party. I head over there and Jane meets me with one of her friends and takes me to the bedroom to dress me. She is very quiet while dressing me and applying makeup and then she snickers as she sends me out 30 minutes later. I walk out and there are 20 or more guys in the room.
Jane and 4 of her friends were there as well. The guys were naked and the girls were taking their clothes off. It looked like it was to be a big orgy except for they were going to tie me up and fuck me. Greg, Josh and Jane tied me up to the ottoman and for the next 4 hours there was a guy in my ass and one in my mouth at all times. About half way through there was a break and I looked around and noticed Marissa come in. Jane went over to her and made sure to point me out. There I was tied down, dressed as a woman with a cock in my ass and covered in cum.
Marissa pulled the guy off of me and kicked me in the balls and said that was for fucking her and cumming in her with my gay dick. She then kicked me twice more in my balls and as I was screaming out and a guy put his cock in my mouth to silence me.
Marissa then went over and undressed right in front of me as Jane grabbed 3 guys to fuck my girlfriend while I watched. They each took turns with her and she must've cum 5 times. They each came over to me when they were ready to cum and flooded my mouth. All this time the other guys were still taking turns with my ass and covering me and my dress with cum.
Marissa went and showered; when she came out she returned to me and kicked me in the balls again. Jane then handed her the vibrator so Marissa could fuck my ass. She rammed the hard dildo into me and I was screaming it hurt so badly. She then left as several guys came over to take their turns at my ass and mouth.
As I was getting ready to leave Jane stopped me and said now that I was free of Marissa, I would be coming over to her house every possible day and night or else. I left there wondering what was up but accepting of the position I put myself in.
Jane calls me the next morning and asks me to come over. I wonder what is up and I am still hurting emotionally and physically from the day before.
I arrive at her house a little after 10am and she tells me to get naked. I comply and she tells me that I am now her boyfriend and slave. I am to undress her lick her entire body and fill her with my cum. I undress her and lick her large breasts, lick her oversized ass and her juicy pussy. She came 3 times and then had me push my hard 7" cock in. It was so nice to fuck a girl again. I filled her pussy with my cum and then she ordered me down to lick her clean.
She made sure as I was dressing that I was hers and I had better come over anytime she wanted. If Greg or Josh still wanted me for their parties she would be present and make sure the guys wore condoms when fucking my ass. I was to come back over later for a little more fun.
I went home a shaved myself smooth as I was told and at 6pm I arrived and there were 3 girls there. They sat me down and stripped me. Jane then got out some clothes she purchased. Thong panties, mini skirt, low heels, bra, silicone breasts, top and wig. They plucked my eyebrows and got me ready to go. By 8pm we were on our way out with fake id's to a local bar. I couldn't believe how much I looked like a tall, shapely hot woman. Jane took me out on the dance floor and we were 2 girls bumping and grinding away. 2 guys quickly came over and one asked Jane for a dance and the other asked me. We were dancing and making out on the dance floor for the next 2 hours. All 5 of us met up with these 2 guys and went back to their place. The guys started having the girls strip and Jane let them know that I wouldn't be stripping but I loved to give head and swallow.
The guys went ands pulled out a box of condoms and Jane grabbed one and jumped on one of the guy's cocks. She had me come over and lick her pussy, his cock, balls and ass while they were fucking. After about 10 minutes he was ready to blow his load. I pulled him out, pulled off the condom and started sucking until he filled my mouth. This went on while each of the girls got fucked and each time I took a load. We were all still drinking heavily and around midnight another guy shows up. He is drunk and sees the sex and naked bodies everywhere. He pulls his clothes off and grabs a condom and me. Jane tells him to leave my clothes on but he can fuck my ass. I quickly reach down and adjust my taped cock forward and pull my panties to one side. He spits on his cock and glides it in my ass. He fucks me for about 10 minutes, grunts and fills his condom before he passes out.
We leave there and head home. We all go back to Jane's house to sleep since her parents are gone and she pulls my cock out the front of my mini and jumps on. She is kissing my lips and commenting how much she loves her new girlfriend with the nice cock while her friends watch. I fill her with cum quickly and she climbs onto my face and lets me lick her clean. We all pass out together and sleep until morning. I get up and make coffee and then come back to lick each girl to orgasm. After coffee and donuts the others leave and we take a shower.
She decides that we should head down to the local adult bookstore to do a little shopping. We arrive about 3pm and the place has a fair amount of guys around. We shop for a while looking at dildo's and strapons. We decide on a strapon that is 7" and we head to the video booths. We slide into one booth; put some money in, lock the door and I strip off my clothes. I hook the strapon around her, put some lube on it and sit down on top of it. I feel it slide deep in my ass and I start bouncing up and down. Within a minute I notice someone in the next booth. Jane whispers through the hole for him to put his cock through. He puts it through and I lean forward to take it in my mouth. I am still moving up and down on the dildo while I am sucking and he fills my mouth with cum. I suck him dry and he pulls out of the hole and quickly leaves the booth. Within a minute there is another cock. I continue sucking on and off for the next 30 minutes taking 5 loads in my mouth. Jane and I kiss after each time and head home. We get to her house and she is so horny, we rip each others clothes off and fucked 3 times.