Tom Loses a Bet

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Tom has to strip for Jane and her friends after being set-up.
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hondo53
hondo53
29 Followers

I'm an exhibitionist and love to be seen naked by women and especially love to be seen with a hard-on. I've always slept naked since I was in high school and one May day in my early twenties I woke up early with a hard-on, not unusual for me. I went into the back bedroom that we used as an office, turned on the light and began to putter around not even really thinking about my nakedness or that we had a fairly large window with no drapes or blinds on it. After about 5 minutes of this I was walking directly toward the window when I looked up directly into the eyes of my neighbor a woman of about 25 who was standing on her balcony watching me. Our eyes met briefly, no more than a second or two and she abruptly turned and walked into her apartment. At first I was worried about what she would think, but as I remembered how long I had been walking around with my boner bouncing in front of me I realized that I really enjoyed having been watched by her. I don't know when my desire to become an exhibitionist started but it may have had something to do with an experience I had earlier.

September of 1971 I left to start my freshman year at the University of Maine in Orono, Maine. Jane a friend of mine since grade school attended a private school in Massachusetts. Looking back on things I realize that I was kind of like Jane's puppy dog. I always wanted to be more than just her friend and so I'd hang out with her in the vain hope that some day I'd be more than a friend. During the fall of my junior year after the soccer season had ended I got out on the highway and hitchhiked down to visit her at her sorority. The weekend turned out to be pretty quiet without much happening on campus and we were talking about what to do when Jane suddenly asked,

"Oh. Do you want to play some pool? We bought a pool table at the beginning of the school year and I'm starting to get pretty good."

I had played a little pool and always enjoyed it so I said, "Sure. Why not."

We headed down to the basement where the pool table was. It was in a pretty big room that was really nicely furnished. There was a fireplace at one end with a couch, a love seat and some really nice overstuffed chairs. A couple of girls were sitting by the fire and said hi to us as we came in. The pool table was at the other end of the room and was really nice. Not like a pool table that you'd find in a fraternity at all. The felt was in perfect condition with no tears and really clean too.

When we came in there were two girls playing. Jane and I watched for a bit. One of the girls was terrible. She could barely even hit the cue ball with her cue. Every time she shot she and her friend would both giggle, as it was as likely that the cue ball would miss all the balls. The other girl though wasn't too bad. You could tell that she had played more and was pretty good at lining shots up and reading the table.

I didn't mind watching because both girls were good looking. Lynn who was the better player was wearing a skirt and a low cut blouse. The skirt was short so that I got a good look at her long legs when she bent over to take a shot but not so short that I could see her ass. And she was really good looking too. Her blouse was tight and really showed off her nice tits. Andrea was pretty cute too and was wearing a pair of tight jeans which really showed off her ass when she bent over to take a shot and a knit shirt that hugged all of her curves. She had nice tits and her nipples were very prominent.

They were drinking beer while they played and offered us a couple, and also told us that they were almost done and then we could play. Although there weren't many balls on the table it took them a while to finish the game and I was on to my third beer. After they had finished they offered to let us have the table but Jane said no let's just all play. So we did. Jane and I played against Lynn and Andrea. Jane was pretty bad too and I was a little better than Lynn so we won the first couple of games.

I'd had more beer than I'd realized and noticed that I was not playing quite as well as I had been, but we still managed to win the third game.

"Hey, let's make this more interesting and play for something," Jane said after the third game.

Andrea said, "Okay, but what do you want to play for?"

"Not, money," Lynn said and got an interesting grin on her face. "How about we play strip pool? If Andrea and I win Tom has to strip for us."

A picture of Lynn and Andrea naked went through my head, but I figured it wouldn't be a good idea to suggest that in front of Jane, so I didn't say anything.

"What if we win?" Jane said. "Seeing you or Andrea strip isn't much of a prize for me."

Andrea said, "Well, okay. What if Lynn strips for Tom and I get Jason to strip for you later?"

Apparently Jason was a friend of Andrea's though not really her boyfriend.

Jane thought for a minute and finally said, "Well, I'm not sure how much I like the idea of Tom seeing Lynn naked, but okay."

I was still fantasizing about seeing Lynn naked and could feel my cock starting to press against my jeans.

Jane looked over at me and said, "It looks like Tom likes the idea. Are you willing to strip for them if we loose?"

I hadn't thought about losing and being somewhat drunk I was not thinking at all about loosing and so I said with more bravado then I should have, "I'll strip for all the girls in the room."

So we started. We decided that Andrea would break then Jane would go followed by Lynn and then me. Little did I know that I wouldn't get to take a shot? Andrea managed to hit the cue ball and direct it into the balls. Jane almost sank the nine ball. But then Lynn proceeded to clear all the stripped balls off the table and sink the 8 ball without missing. About half way through I noticed that Lynn was now shooting with her right hand not her left, as she had been when we first started. After sinking the 8 ball she set her cue on the table looked at me and grinned a big grin.

Andrea looked across the room and called, "Hey girls. Jane's friend is going to strip for us," as she did I could feel my face getting hot.

Lynn noticed and said, "Oh bashful too. I like that."

Turning and looking to the other end of the room I noticed that some other girls had come in while we were playing and now there were about 10 of them. At the same time the door opened and 4 girls walked in, one of them saying, "Did I hear that there's going to be a stripper?"

I heard some one else say, "Alright! Let's do this right. Pull the table over this way."

The girls by the fireplace turned their chairs so they were facing away from the fire place and out into the room while a couple of other girls dragged a round coffee table over in front of the chairs. Other girls were moving the sofa over. Jane and Lynn moved over to stand one on either side of me and started to direct me over to the other end of the room, while Andrea took the cue from me. As we got to the table Lynn put one hand on my back and saying, "Get up there," they pushed me forward till I stood up on the table. Some one had turned on some music and now the girls were starting to hoot and I heard girls saying, "Alright," "Take it off." I also noticed that some of the girls had cups and were drinking. The door opened again and several more girls came in carrying several bottles of wine with them.

I looked over at Jane standing between the couch and one of the chairs and she just smiled at me and shrugged.

I thought to myself, "What the Hell have I gotten myself into? Then I thought to myself that I'd just strip down to my underwear and stop there."

I crossed my arms at my waist, grabbed the sides of my t-shirt and pulled it up over my head making sure that I raised my arms nice and high and pausing for just an instant with my shirt covering my face. There was more hooting and someone whistled. Then I pulled the shirt off and tossed it over to Jane. She caught it and smiled at me. Next I turned to face away from most of the girls, spreading my legs a bit and bent forward at the waist. I untied my shoe, slipped it and my sock off, and stuffed the sock into the shoe. Standing up I turned and tossed that to Jane too. I turned again this time having my back toward a different group. Again I bent forward at the waist and removed the left shoe.

Turning to face the main crowd I spread my legs a bit and put my hands to my waist. I pulled the end of my belt free with my right hand holding it against my palm and slowly pulling. With my left hand I released the buckle and pulled the buckle slowly separating the two ends of the belt and holding them with my hands spread. Turning slightly to the right I slipped my thumbs behind the waistband of my jeans with my fingers over the front. And pulled the waist forward and down a little. Sliding the fingers of my hands to the middle I unbuttoned my jeans and pulled the two flaps forward and down. My jeans were low and this revealed the top of my white underwear. I was wearing a pair of white cotton g-string underwear that Jane had gotten for me and asked me to wear today.

I moved a bit and turned again trying to be a tease. The girls continued to hoot and whistle. I tried dancing around a bit on the table trying to tease the women. Using the index finger of my right hand I flicked the tab of my zipper up and slowly pulled my right and left hand apart and down opening the front of my jeans and revealing my underwear with my hardening cock straining against them. I pivoted on my right foot and faced with my back to the crowd and my legs spread at the same time moving my hands along the waist of my jeans until they were at my sides. Bending forward I pushed the jeans down until they were at my ankles, there was a loud cheer, some whistling and more hooting. I stood up, lifted my left foot and pulled it free of the jeans at the same time making a half turn to the right. Then I lifted my right foot and kicked out in Jane's direction. My pants flew off and landed on the floor in front of her. The girls clapped and cheered.

As I turned to face them someone yelled, "Wet underwear."

Next thing I knew Lynn was standing in front of me with a small pitcher. She was smiling at me and using her index finger beckoned me. As I moved toward the front of the table she reached forward with her left hand, slipped her index finger into my underwear and pulled them forward. My cock was completely on display for her and she glanced up at me and smiled an even bigger smile then she slowly poured the water directing onto my lower abdomen, my cock and around my underwear. She released my underwear and then cupped her left hand under my balls, poured some water into her hand and then rubbed it onto my underwear. She did this about three more times until she was satisfied that my underwear were really soaked. As she stepped away there was a loud cheer and clapping, and I looked down to see that my underwear were now completely see through.

As I turned to show the rest of the crowd one of the girls stepped onto the table and started to dance with me. She was wearing a short jean skirt that showed off a lot of her legs and she moved in really close to me straddling my right leg with her legs. As she danced she moved down until she was squatting in front of me with her legs spread. This pushed her skirt up and revealed a pair of colorful stripped panties. As she moved up again she lost her balance a bit and fell against me pushing on my cock with her hip and waist. I grabbed her arms to steady her and she grabbed me by the waist and started to gyrate her hips humping against my hard cock. While I was enjoying the feeling of her pressed against my cock I felt some hands on my back and looked over my shoulder to see Lynn behind me dancing too. She put her hands on my hips and pulled her self in against my ass and rubbed her crotch against me. Eventually Lynn moved around to my left, with her right hand on my back and her left hand on my chest she humped my side for a bit. The other girl had taken a similar position on my right. We danced like this for a bit and then as if on a signal both stepped back, took hold of my thong and pulled it down past my knees. I made a grab for it but was too slow. Lynn made me step out of my thong and held it up over her head as the women cheered and hooted and my cock bounced in front of me. Then she threw it into the crowd. There was a brief scramble and then Andrea stood up and held my thong over her head while the women cheered and laughed some more.

As the women cheered some of them moved toward the table and started to grab my cock and my ass. I tried to push the hands away but there were too many of them and some grabbed my arms and held them to my sides.

I heard some one yell, "Beat him off."

And some else yelled, "Yeah. Let's see him shoot his load."

Next thing I knew someone was stroking my cock.

Girls started yelling that they couldn't see and others yelled for people to sit down.

Girls started to return to their seats but two of them stayed there and got up onto the table with me. The girl standing to my left had her left hand around my cock and was pumping me. The girl on my right had her right hand on my ass and had slipped her finger into my ass and was rubbing my prostate while she squeezed my balls with her right hand.

Andrea stepped in front of us and said, "Here, use this," as she held out some lotion. The girl who was stroking my cock stopped and held her hand out for Andrea to put some lotion on. Then she took my cock in her hand again and started to stroke up and down with long strokes. After about a minute I could tell I was about to come and I involuntarily arched my back thrusting my hips and cock forward. The girl sped up her stroking. My head rolled back and I grunted and shot a glob of come high into the air followed by another and another. It was perhaps one of the most intense orgasms I've ever had and all the girls started to clap, cheer and laugh. Andrea came back over with a washcloth and a towel and cleaned me off. I felt drained after such a powerful orgasm and had my head down with my eyes closed while Andrea spent more time than was needed to wash off my cock and balls.

She said that she enjoyed the show and was glad that Jane and I had lost. I looked over to where Jane had been but she was no longer there. I looked around the room but couldn't see her anywhere.

Andrea held her hand up to me and I took it stepped down off the table. I was starting to recover from my orgasm and realizing that I had just let someone beat me off while a room full of girls watched and that I was still naked. I was thinking that I should get dressed and get out of there, but I felt like I was still in a daze and just let Andrea lead me wherever. The other girls were milling about and several came by and said, "Nice show," or "That was great," and as they did they would grab my ass or put their hand on my chest. A couple even grabbed my cock or squeezed my balls. One girl who looked pretty drunk came up to me and leaned against me pushing her tits against me and putting her right hand around my waist to the back she rubbed my back and ass. Her right hand she put on my chest and rubbed my chest and even pinched my right nipple between her fingernails. While she put her right hand on my ass she moved her left hand down to my stomach and paused there and then moved it down to my abdomen and paused and finally moved down and grabbed my cock and balls. Then she leaned her head forward and sucked my left nipple into her mouth while she gave my cock a few strokes.

Andrea took my right hand and pulled me away. The girl moved her head forward and sucked until my nipple was pulled from her mouth and finally my cock was pulled from her hand. She smiled as I moved away and said," See you later."

"Let's go find Jane," Andrea said as she led me still naked from the room.

hondo53
hondo53
29 Followers
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4 Comments
AnonymousAnonymousover 10 years ago
Just say "No"

End of silly story before it starts.

AnonymousAnonymousover 13 years ago
Wow

Lucky Tom

AnonymousAnonymousabout 15 years ago
Not enough suspense

The outcome was obvious from the start.

<br /><br />

Some reluctance would make a story like this more entertaining and stimulating. Some penalty stripping by both teams would have been good, even if the protagonist was the only one who ended up nude.

AnonymousAnonymousalmost 16 years ago
Great Story

A great cfnm story I look forward to reading the next part

Thanks for a great read!

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