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Richie's Lost Bet

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Richie’s Lost Bet

In the year after I graduated from College my friends and I continued to visit with each other regularly. I had a job in the city which was about two hours from campus. So on a frequent basis my friends who were still in school would come to town and we would hang together. In between I would pack up and go back to campus and hang with them too. For me this was a really great transition from being a full-time student to working in the ‘real world’.

While I consider myself relatively tame and conservative, none of my friends are really wild party people either. But from time to time things would get really out of hand. The events of one of these wild times will remain indelibly imprinted in my memory.

I’d gone back to campus for a weekend Halloween Party. I’d almost decided not to go. I had the Fall ‘blues’ and did not really want to go back to campus only to have to leave my friends missing them even more. In the end I hopped in the car and took off. And boy am I glad I did!

Friday night on campus was typical. Lots of frats were having parties and people had started drinking long before I arrived. My friends new I was coming and was having a low-key get together in our dorm (their dorm). When I arrived there was an intense “discussion” going on about one of my friend’s sexist generalizations and comments about women. Richie was notorious for provoking the girls and riling them up but generally we all considered his remarks harmless and not indicative of his true thinking. None the less, he could get really raunchy especially when a little alcohol was involved.

To this day I really don’t know what started the argument but I arrived to know that Monica, Sue and Karen were really pissed with Richie. Usually the guys would pile on and inflame the situation but not this night. We played drinking version of Trivial Pursuit. As no surprise the game turned into a battle of the sexes with Richie, the biology major, insistent that women were just not ‘wired’ for science the way men were.

As luck would have it the girls were winning which only raised the stakes on the brewing confrontation. Finally, Sue made it to the final question to win the game and Richie was pissed! And then the bet was made. Sue bet Richie that she could answer any “science category” question asked. Richie took the bait and said no limit on the loser’s fate. Sue pressed again… Asking Richie if he was sure he wanted to place such a risky bet and guaranteed she would utterly humiliate him if she won. Richie could back out at this point and sure enough Richie asked what sounded like a really tough science question and Sue nailed the answer.

The girls were hysterical! And the taunting started immediately. Richie was red-faced and embarrassed just at having lost to the girls. As well as having been maneuvered into further shame. That’s when the discussion turned to “consequences’ for Richie and things got really interesting. There was talk of Richie cooking, cleaning and doing the girls laundry to put him in his place. There was talk of dressing him up like a girl and parading him around campus. And finally that talk turned into a plan about what Richie would wear to the Halloween costume party planned for Saturday evening.

Sue told Richie to be ready to go shopping for his costume the next morning at 11:00 a.m. sharp. Sue and Richie would go to the mall by themselves to get Richie the costume the girls had decided. With that we all decided to call it a night. I was staying with Richie and his roommate, sleeping on the floor.

As Richie, Bob and I settled in for the night we began speculating on how evil Sue was going to be. We imagined a French Maids costume, a cheerleader –short skirt, pom poms etc. Finally Bob suggested a male stripper. The more we laughed about that idea, the more Richie realized he might have gone too far. He kept saying “she wouldn’t do that to me”. WE finally said that there really would not be much need for shopping if that was her plan. But we did suggest that Richie be especially humble and apologetic in the morning because the consequences could be dire.

In the morning Bob and I avoided further speculation but Richie was clearly nervous. After breakfast together Bob and I planned a game of racquetball while Richie was headed to the mall with Sue. Over lunch Bob and I continued to imagine how ruthless Sue and company were going to be in humiliating Richie. It’s worth noting that Richie and his dealings with women were always a topic of conversation.

Richie had never had a girl-friend or even a serious date to speak of and here he was a senior in college. Bob and I wondered out loud if Richie’s demeaning talk was due to his lack of comfort being close with women or if there was something deeper. Regardless, Richie was clearly a hot topic for conversation all around and clearly inexperienced sexually. That he was 6 feet 3 inches, athletic, slim and sported very cute coppery red hair only helped to fuel the talk – guys and gals alike. I’d come out to Bob during college but not to the rest of my friends. We had both speculated out loud that Richie might be wresting with his ‘identity’. If I didn’t think it would totally traumatize him, I would have come out to him too and considered a relationship.

After lunch we were back at the dorm when Richie and Sue arrived from their trip to the mall. It was instantly clear that Sue was gloating and Richie was mortified. Sue and the girls came over to Bob and Richie’s room and there was non-stop giggling and glee that could not be missed. Finally I asked the question… “So Richie… what will you be wearing to the costume party?” When the girls lost it in fits of hysterical laughter I knew! Karen said “Go ahead and tell them Richie! They find out soon enough!’ In fact, why don’t you go and try on your costume so we can preview it before tonight.”

Richie had not said one word. But his red-faced silence spoke volumes about his impending humiliation. Finally Sue told Richie she wanted him to go and try on the “costume”. Richie protested weakly and finally left the common room to change in the sleeping room behind. It was clear that Sue had not shared the details of the costume with her girlfriends… only that her revenge would be priceless. So we waited and we speculated.

Finally Richie emerged from the bedroom. We were totally speechless at the sight of him. He was bare-chested wearing a silk purple bow-tie and silk purple boxers. His fine red hair on his pecs and legs were hot! Bob and I had seen Richie in his boxers on many occasions. But this outfit clearly hit a sexual chord! The tie highlighted his chest. The boxers highlighted his long bare legs. One could not help but imagine what lay above the bottoms of the boxers and below the waist-band.

As we laughed, Richie blushed a shade of crimson I’ve never seen before or since. Sue asked if Richie had put on everything and he replied that he had. And we were all curious since he was covered in so little. The boxers were loose but cut high and open quite a bit on the sides. As we took in this spectacle, I really have to admit I was turned on. I was worried I too was a revealing shade of red and was experiencing a stirring in my jeans that I hope was not apparent. Thank god all eyes were on Richie!

Finally Sue instructed Richie to show us the rest of the costume. After some serious hemming and hawing, Sue threatened to take matters into her own hands if Richie did not do what he was told. With that Richie hooked his thumbs in the purple boxers and time seemed to stop as I realized he was about to slide the boxers down his legs. By now I was downright hard as a rock and Bob new it. I could not peel my eyes away as Richie slid the purple boxers down his legs to reveal the tiniest black g-string I have ever seen.

Richie could not make eye-contact with any of us. And I could not take my eyes off his body. I looked up and down from his red-face to his bulging package. The g-string seemed to barely fit him. Tufts of coppery pubes popped out above. The bulging pouch seemed at risk of exploding. After a deafening silence, everyone burst into laughter…except for me. Richie and I had locked eyes while the girls and Bob were hysterical.

Then Sue went on to explain that Richie would start the evening dressed as a male stripped and that at her direction throughout the party he would slowly shed the tie, the boxers and ultimately the g-string. The harsh lesson was intended to cure Richie of his sexist stereotypes and prove that he was not superior to any woman.

Richie was silent. Bob could only observe that ‘paybacks are hell”. I said that perhaps Sue was going a bit too far and that Richie’s humiliation should be limited to our group since that’s where the damage had been done. None of that mattered to Sue. Throughout Richie remained silent. (Probably the best idea.). Finally Sue instructed him to remove the g-string. And again we were speechless. I didn’t want my good friend embarrassed this way but I could not help but want to see him thoroughly and totally embarrassed.

After what seemed like an eternity Sue approached Richie and threatened to physically remove his last bit of cover. Richie tried to beg and negotiate but Sue would have none of it. Finally Sue tweaked Richie’s nipples causing him to shift his hands up from covering his crotch and allowing her the opportunity to grab at his cock. His cock twitched and none of us could miss it. At that moment I knew.

Richie’s g-string came down in seconds and there we all were speechless and gawking.

While I had seen Richie naked and seen him with a raging boner in his undies, I’d never seen him totally boned up and totally naked at the same time. And there he was in all his glory. Richie’s erect cock was gorgeous. While he tried to cover it Sue started to tickle him and Monica and Karen joined in. Bob and I did not move to help. Finally they girls stopped leaving Richie gasping for air, totally exposed, erect and leaking pre-cum.

Unexpectedly, Sue chose this moment to leave. She announced that they would “SEE HIM” later and that Richie might want to use the time before the party to clean himself up and prepare. Sue’s final comment that Richie’s arrogance would end and it would be fitting if he were to totally lose control of himself in front of all those he had ridiculed over the years.

Bob and I were now alone with a naked, hard leaking Richie. Neither of us knew what to say. Finally I broke the ice. I said “Richie you really want to make sure you don’t go the party before you jerk-off. It would be unimaginable to have an orgasm in front of the girls and everyone at the party.” Bob was speechless and decided to leave the room. I was speechless but could not take my eyes off my naked and erect friend.

Finally I asked Richie if he wanted to be alone so he could jerk-off. When I said this it was like a cannon went off and Richie realized the total shame he was in for. Quickly Richie dressed. And then he just wanted to get out of the dorm. We went for a run together from campus to the lake to the park – as we had done many times when I was still on campus. When we stopped at the park Richie finally broke down. He shared that he was mortified to go through with his punishment and also that he knew he could not chicken out. He could not seem to find a way to avoid the situation. And he could not accept it either.

After a long time being alone together I suggested that Richie could go and beg Sue for a reprieve in the form of a private humiliation or that I could go and beg on his behalf. That Richie was always privately (as opposed to publicly) ‘abusive’ or derogatory should count for something. In the end Richie decided it was entirely up to him to try and get himself out of the mess he’d gotten into.

I knew in my heart Sue would be unrelenting! She was angry and intended on total humiliation. On top of that, as shy as Richie could be, she also knew he would never chicken out. As for me, on one hand I wanted to see my friend spared the humiliation and on the other hand I could not wait to see the Richie, naked, aroused and who know what else in public!

Suffice it to say, Richie tried to appeal to Sue, Monica and Karen. Sue refused to give in! She told Richie she loved his begging and hoped it would continue into the evening as it would only add to her enjoyment.

Finally the time came to head to the Halloween party. I had no costume. Bob went as a lame orchestra conductor. Richie… well… he was dressed in his bow-tie, boxers and a pair of flip flops when Sue and crew came to collect him. As I waited with him, I realized that he had still never ‘relieved’ himself. His bulge was unmistakable to me. In my heart I knew that Sue would not be satisfied until Richie was thoroughly and completely humiliated. That meant totally bare-ass naked and hard for all to see. I also knew it would not take much to push Richie over the edge. As much as I wanted him spared, I also wanted to see Richie brought to climax, moaning and grunting like a bitch in heat.

As the girls escorted Richie into the party the room went wild with camera phones snapping pictures right and left. Girls were cheering and beside themselves with laughter. Guys were making fun of ‘naked Richie’. Sue instructed Richie that he was forbidden from using his hands to cover himself and that if she caught him, she would have him strip naked on the spot and cuff his hands behind his back. Again, I was turned on. And Richie was redder-faced than his hair.

As they moved into the room I was shocked at how quickly the girls in the room proceeded to physically reach out and touch Richie. They were tweaking his titties and grabbing at his ass. As I watched closely, I could all of this was having a reaction and that Richie’s cock was getting firmer and firmer. His nips were totally hard and with every touch I watched his toes curl and his cock lurch.

Bob had brought Richie a drink to help calm his nerves since it was going to be a long evening for him. What none of us knew was the Bob had spiked Richie’s drink with a little Viagra to insure the evening’s excitement. Richie’s really did not need this to be totally aroused and it certainly had an effect on the events that followed.

Sue toured the room, Richie in tow. After everyone had a chance to see Richie up close and personal, Sue seemed to settle down and allowed Richie to wander around on his own. He came to hang with me. I was turned on that he found comfort in being with me and aroused standing so close to his nearly naked body – which I tried desperately to ignore standing next to him. While neither Richie nor I drank much, Bob kept us both supplied with cocktails. I was convinced my hard-on was directly related to Richie’s undress. I thought his bulge was largely due to his public exposure.

After about an hour when we all started to relax and Richie seemed to have gotten over being at a party in a bow-tie and underwear, Sue, Monica and Karen chose to act, announcing a special Halloween surprise. Asking Richie to join them at the center of the room they described how it came to be that modest Richie had forced into / out of his Halloween costume. Sue went on to explain that Richie would be shedding pieces of his costume on her orders through out the evening. The way Richie would lose or keep his outfit would be to answer “Science Questions” proving his male lack of superiority to women. Correct answers bought 15 minutes until the next questions. Incorrect answers resulted in removing an article of clothing.

Keep in mind Richie was wearing a bow-tie, flip flops, boxers and a g-string. It was clear where things were headed. The only question was how long it would take to divest Richie of his skimpy costume.

It’s no surprise the first question was impossible. Richie lost his flip flops. While it’s hard to imagine that these provided any real cover, the effect of his losing them was huge to all assembled. Fifteen minutes later, Richie lost again. This time Sue wanted the boxers! Wow! Richie was stunned and so was I. The g-string seemed to strain and pull against Richie’s hard cock. Sue let this new state of nudity sink in for a little while. Her timing was masterful.

Richie stayed close to me. But lots of people approached, grabbing a bit of ass, crotch and titties. Finally I could see pre-cum seeping through the g-string. And Sue was ready! The next question was obviously unanswerable and Sue wondered allowed if it was time for the tie or g-string. The crowd was unanimous! G-STRING had to go.

Approaching Richie from behind, Sue slipped her hands around his waist and caressed his nips. Then she instructed him to place his hands behind his neck. Uh oh! I was rock solid. Richie was almost bursting forth and oozing a lot. Slowly Sue slipped her fingers in the g-string teasing everyone. She slid the back up and down. Following suit, she slipped the front over the tip of Richie’s cock and teased us all. Richie gasped out loud at the added stimulation.

I thought he would blow right then and there! Finally the deed was done and the g-string was lowered pulling Richie’s erection out and down. It must have painful. Finally his cock sprung free, bouncing straight up and out. People screamed. I almost passed out. Bob stared mouth agape. Richie‘s cock twitched and bounced and his toes clenched. I could tell he was in serious trouble! Hands still behind his head, tie in tact, Sue stepped forward for a full frontal view. What happened next shocked me!

Karen produced a tape-measure while Sue explained that they would totally document Richie’s shame so that he would never forget. Hands still behind his head, they proceeded to measure Richie’s foot size, then his waist, onto his inseam. Finally and inevitably it was time for his straining cock. His cock was long and slim. 7.5 inches stem to stern. The more they played and fiddled with it the more Richie squirmed. I could see his face, toes, and tits. All were firing on every sensitive stroke.

Finally Sue pulled his cock straight down, stroking under his head and letting it snap up against his belly and that was all it took! I saw Richie lose it in that moment. Every muscle went rigid. His mouth gaped and finally he started to gasp and moan… “No, no. NO! Oh no! and AGHHHHHHHHHHHHHHHHHH” as he exploded on the spot. Jets of jism flew for at least 30 seconds. Richie convulsed, shuddered and lost his balance almost collapsing. After a deafening silence, the room roared with laughter.

I was speechless. And leaking copius pre-cum through my jeans. Bob was on the floor laughing. Richie stood motionless as the convulsions of his orgasm subsided. I grabbed him by the hand and lead him out of the room to wild applause.

By the time we got in the room and I had locked the door, Richie was rock hard again. All he said over snd over was “I can’t believe this!” He noticed I was sporting a boner and this brought him out of his stupor. As we stared at eachother, I realized the lust we shared in that moment. With the door locked, I stepped forward and grabbed his beautiful erection while he stated pulling me out of my clothes. I was naked a blew in less than a minute. Richie came again in my hand and once more!

We locked Bob out!

The next day it seemed surreal until pictures of Richie began surfacing around campus. From that moment, Richie was cured of demeaning women. And he realized how sexually charged and pent up he was. To this day when we talk about this story we both end up with major orgasms!


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