The Bet

Let me first setup the situation, I have been friends with this guy for about the last 10 to 12 years. His girlfriend, Tyler, had this friend named Jen. I was totally in awe of Jen, she was so beautiful. I am not exactly good with the ladies, so when I finally asked her to go out, she gave me an emphatic "NO!!" So now she knew that I liked her, she took full advantage of it. She would dick tease me all the time, she would take her shirt off and walk around in a bra, and she knew that I couldn't stand it.

So after about a month of this teasing, I finally told her that she was only doing it because she knew that I wanted to fuck her. So she said, "Okay, well how about this, I'll make a bet with you." She went on and told me that we could each write down 4 things on a piece of paper. She went on to tell me that the loser of the bet had to do the 4 things that the winner wrote down on the piece of paper. I agreed and started to write down the things I wanted her to do. Number one was that Jen had to fuck me, number two was that Jen had to give me a blow-job, number three was that I got to eat Jen's pussy, and number four was that Jen had to go skinny dipping at my house at least five times during the summer.

The bet was that Jen could make me cum in less than 3 minutes, I liked her, but I didn't think that she could do it. We both got all set-up, I sat down in a chair and took off my pants. I already had a hard-on, she slid a condom on my stiff dick and started to lower herself on my dick. Before she got to my pee-pee, I had a huge orgasm. Jen and Tyler both laughed their ass off at me. I had lost the bet and felt dejected.

Minutes after my knee-shaking orgasm, Jen handed me the piece of paper that she wrote her demands on. I unfolded the piece of paper and started to read, number one was that I had to eat my cum anytime Jen wanted me to, number two was that I had to take a gang facial from 15 of Jen's buddies whenever she wanted me to, number three was that I had to suck any guy's dick that she wanted me to, and number four was that anytime I was around Jen, I had to wear a bra and a pair of panties.

Immediately after I read the demands, she told me to stand up so that she could take the condom off, she did and handed it to me and told me, "Eat your cum, pussy!!" I did as I was told and dumped the cum into my mouth and swallowed it down. She then looked at me and said, "Let's go to Wal-Mart and get you some bras and panties, you faggot!!" Then she laughed and said, "and also, you have the smallest pee-pee I have ever seen, I think I am going to call you Stubby-Dick from now on." Tyler and Jen had a good laugh at that too. The sad thing was that she was right, I do have a tiny little pee-pee. My pee-pee is only 3" long when hard and 1 ½" in girth when hard.

We headed to Wal-Mart and when we got there she asked me, "have you ever worn bras and panties, and TELL ME THE TRUTH!!" I lowered my head and replied, "yes, I have worn them before." She then said, "well what size bra and what size panties do you wear?" I meekly replied, "I wear size 8 in panties and a 38B bra." She looked at me and said, "you are such a little pussy, most guys would have to wear like a size 14 panties, not you, you still wear panties that other girls can wear, just because your pee-pee is so pathetic!!!" I lowered my head and sighed.

We got into Wal-Mart and headed to the Intimate section. She started looking at panties and picked out a pair of pink satin string bikinis with little red hearts on them. She picked up about four pairs of them and said, "we are going to get quite a few, so that you aren't always wearing the same ones, Stubby-Dick." She headed towards the bras and found three bras that perfectly matched my panties. The bras she picked out were very padded, I read the sticker on the cup of the bra and it said, "GIVES YOU A 3 CUP BOOST!!" I knew immediately that Jen was going to pick those bras, just because it would actually look like I had D-cup breasts. Jen headed towards the desk and quietly talked to the lady watching over the Intimate section. They both started giggling and Jen waived me over and told me to go in the dressing rooms and try on the bras. I did and put my shirt back on and headed out, Jen looked at me and said that will do. I looked down and saw my chest sticking out, it actually looked like I had breasts.

As we headed towards the register, Jen said, "I am going to tell the lady that these bras and panties are for you to wear." She immediately started laughing and then added, "Oh cheer up Stubby-Dick, you deserve to wear bras and panties, because you sure as hell ain't no man with that tiny little thing you call a penis!!" She started laughing hysterically at me. We got to the check-out and Jen looked at the girl working and said, "these bras and panties are for him, he has to wear them because he has a 3" pee-pee." Jen and the girl working both had a good chuckle at my expense. We checked out and headed towards the car.

As soon as we reached the car, she told me, "put your bra and panties on right now!!" I started to undress and quickly put my bra and panties on.

Jen started dialing her phone and started talking to some guy. She said, "Hey, get the guys together, I got a dude here that has to take a gang facial whenever I want him to, we are on our way right now." She hung up the phone and told me to head towards her old school. I told her okay and started driving towards the school she used to attend.

She directed me towards the house we were going to and I drove right there. I was actually kind of excited, I had always wondered what it would be like to have a gang facial. We got there and she told me to get out of the car and we headed towards the front door. We walked in and I saw 15 guys standing there, all naked with big cocks swinging in the wind. Jen demanded me to take off my shirt and pants and get on my knees in the middle of the circle that the guys there had formed. I did as I was told and got on my knees, one guy stepped forward and slapped me in the cheek with his 8" cock. Everyone started laughing and this guy proceeded to shove his cock in my mouth. He started to pump his cock in and out of my mouth and I actually got a big hard-on. Jen started yelling at me and said, "YOUR FUCKING ENJOYING THIS, YOU FAGGOT!!"

The rest of the guys started to step forward and shove their cocks in my mouth. After I had taken 4 cocks in my mouth, I heard a guy towards the back say, "I am going to cum, GET OUT OF THE WAY!!" He stepped forward and started to jack-off in my face. Jen told me to open wide and I opened my mouth and stuck my tongue out. After about one minute of jacking-off, his balls started to retract and he shot a huge load of steaming hot cum all over my tongue and some even went in my eyes. I closed my eyes so that the cum wouldn't start burning them. That is the last I saw of the 15 guys until they cleaned me up. All I remember was I took about 20 cumshots all over my tongue and face. When I opened my eyes, all the guys were standing around smoking a cigarette. Jen looked at me and laughingly said, "you better get used to that, we will be back here quite a few times!!" I lowered my head and got dressed, and Jen and I headed to the car.

Jen told me she would drive, so I handed her the keys. We hopped in the car and headed off. As we were driving down the road, I looked at Jen and asked, "Jen, can I masturbate?" She looked at me and nodded her head in approval. I reached down and unzipped my fly and pulled out my tiny little pecker. I quickly started beating off and within about 2 minutes, I was cumming in a glass that Jen had handed me. After I milked my cock for all the cum it had, Jen looked at me and said, "Go ahead stubby-dick, suck down that cum!" I lifted the glass to my mouth and tilted it back and let the cum run into my mouth. I swished the sperm around in my mouth for a while and then swallowed it. Jen looked at me and started laughing and said, "you are such a little sissy!!"

We drove to a party about ten minutes away from the house that we were just at. When we got there Jen immediately started talking to a guy that she knew. She grabbed his hand and walked right up to me. She introduced him as Johnny. I shook his hand and asked him how he was doing. He replied, "I am doing great now that you are going to suck my cock, you little faggot!" Jen led me upstairs and took me into a room and turned on the light. Johnny followed us and shut the door behind us. Jen sat down on the bed and told me to get on my knees. I did as I was told, and then took off my shirt. Johnny dropped his pants and moved towards me.

His cock was at least 9 inches long and really thick. He slapped me in the face with his cock and yelled, "open your mouth you little sissy faggot!!" I opened my mouth and Johnny slowly slid his monster cock in my mouth. Much to my surprise, I was able to get the whole cock in my mouth. I started to slowly move up and down on his giant member. He was moaning and groaning and I could tell that he was getting close to cumming.

Sure enough he started to yell, "II-MM CUU-MMMIINNG!!!!!" I felt his cock start to pulsate and soon felt him shoot his cum straight down my throat. Johnny shot six streams of hot cum down my throat. His cock fell out of my mouth with a plop and he collapsed on the bed. He looked at me and said, "GOD DAMN, that was the best fucking blow-job I have ever had you sissy little bitch!!"

Jen looked at me and said, "Stubby-Dick, thank Johnny for letting you suck his cock, and thank him for his precious cum." I looked at Johnny and said, "Johnny, thank you so much for letting me suck your gigantic cock and thank you for letting me eat your delicious cum." Johnny just nodded and added, "my pleasure sissy fag!" Jen looked at me and said, "I can tell that we will definitely be back here!"

I have been getting gang facials and sucking dick for the last 8 months. Jen and I have since decided to date so that it won't look suspicious when we are together all the time. I visit Johnny about twice a week and I get a gang facial about once a week. I eat my cum about four times a day and get to eat Jen's cunt at least once a day. I have since started wearing panties all the time. I have replaced my entire underwear wardrobe with all satin string bikinis. I still wear bras, but not very often, Jen doesn't want anyone to know that she dates a guy that wears bras. Jen and I very happy with our lives and are thinking about getting married so that we can do this for the rest of our lives. To this day, Jen and I still haven't had sex. She always tells me that there is no reason for us to have sex, she won't even be able to feel my pee-pee in her pussy.