Pin the Tail

A young cuckold watches his loving girlfriend pleasure other boys.

*

Young Connie was on her knees diligently working the big, hard cock with her little mouth. The other guys were watching carefully, admiring her skill and hoping they could go next. The only problem was that the cock she was sucking did not belong to her boyfriend, Ricky. He too was watching everything, but in a confused state of mixed jealousy and arousal. Pour yourself another drink and sit back while I relate a tale I managed to extract from my sexy wife about the first time she was shared with other guys. She claims not to remember much so I used my twisted imagination to fill in the details.

It was a summer after high school when everyone was young, trim, beautiful, moist and horny.

Some of the kids were having a pool party and since the parents were away, some of the guys snuck in some beer and vodka. The guys were in their tight board shorts and the girls were in their little bikinis. These were mostly the cool kids, the ones with the rich parents and the nice cars and the ones who were all going off to the fancy colleges. The boys were all hormones, hairy legs and six-packs. The girls were all skinny, pretty and care-free.

One of the girls who Connie knew invited Connie and Ricky to join her at the party. Maybe she was taking pity on one of the girls who wasn’t part of the ‘in’ crowd, or maybe she wanted a loser there to make her feel better about herself.

But Connie was no loser. She was smart and had quietly worked her way into the upper percentiles of the class ranking and under that relatively modest two-piece swimsuit was a budding beauty, her body toned into firm smoothness as she jogged and biked around town.

**************************

She and Ricky had been doing a lot of experimenting over the past few years. Their young bodies were always hot and tingling and whenever they could be alone they couldn’t keep their hands off each other. Things got much easier once Ricky started to drive and they discovered, as they say, paradise by the dashboard light.

Ricky couldn’t help himself. When they were making out in the car there was something about the way Connie responded to him that drove him crazy and filled his mind with crazy feelings. He loved the way she surrendered to his attentions and he always wanted to get her to do more. While she always tried to resist the way she knew good girls should, she couldn’t always do that and would sometimes succumb to her own inner desires. When she did finally give in and open herself to him and get all wet and slippery inside, Ricky’s head would start to buzz and he would have thoughts about her that he was almost afraid to examine.

Ricky loved Connie’s tits. They were full and firm and as she matured her nipples grew large, brown and responsive. Ricky discovered that if he could get her to let him suck those nipples they would grow hard in his mouth and she would moan and let him do almost anything. They had already fucked a few times in that awkward, fumbling way of teenagers when they first discover each other, but what Ricky really loved was getting Connie to go down on him. Connie was reluctant when Ricky first coaxed her into kissing him “down there,” but with him coaching her to do it in the ways that felt best, together they made her into something of an expert at getting him off. Connie was a girl of great conscientiousness and determination. When she started a job, her greatest desire was to finish it and that meant when she started sucking Ricky, she took him all the way to completion.

**************************

One evening they were parked in their favorite spot down by the beach. They were really getting into the heaviest of petting and once again Connie was on the verge of finishing Ricky in her mouth. Suddenly and unexpectedly there was a knock on the steamed-up window. Terrified that it was the cops, they scrambled to cover up, but it was only Deke, a kid they knew from high school.

“Shit, Deke, you scared the crap out of us!” exclaimed Ricky after he rolled the window down a crack.

“Look at you two! Who knew!? What’s going on in there?” asked Deke.

“Oh, we’re just watching the submarine races,” answered Ricky as Connie tried to cover her naked breasts with her t-shirt.

“Submarine races? It looks like someone was going down, alright! Be careful, now. Don’t do anything I wouldn’t do! Are you guys coming to the party?”

Ricky got rid of Deke as quickly as possible.

“Whew! That was close!” he exclaimed.

“Close! He saw everything!” Connie responded.

“Nah, I don’t think so, but he sure seemed interested in what you were doing.”

“You think so?” asked Connie with some embarrassment.

“Yeah, and I’m sure he wishes he had a girl that would do what you can do. Maybe you should show him some day.”

“Cut the crap, you pervert. You know I only would do that for you,” she said with a little smile as she reached over to help him open his pants again to continue where she left off.

“Oh, God,” Ricky moaned as he felt her take him in her warm, wet mouth again. “You’re so good at that. Don’t stop. You’re such a bad girl. Oh, you’re beautiful. You’re fantastic! Don’t stop! I’m going to shoot!”

She didn’t, and he did.

**********************

It turns out that the party was at Deke’s parents house. The guys were drinking the beer and somebody made a punch with the vodka for the girls. Everybody was having a good time grab-assing around, throwing the girls in the pool and having chicken fights in the water with more than one bikini top getting pulled off to the delight of the crowd. Somebody even tacked a ‘pin the tail on the donkey’ game to a tree and the kids got plenty of laughs as their drunk and blindfolded friends tried to hit the target.

As the sky darkened and the number of party-goers dwindled Deke said:

“Hey, these mosquitoes are getting bad, let’s go inside.”

Only Deke, Ricky, Connie and a couple of other guys who came without dates were left. They went down into the walk-out basement. They brought the pin the tail game and more drinks with them. One of the guys gave Connie more punch and someone taped the donkey’s ass to the wall. The guys stood around in a semi-circle to watch as everyone took a turn. When it was Connie’s turn with the blindfold she stumbled toward the target but veered off course and bumped into one of the guys. He laughed happily, took her by the shoulders and kissed her on the mouth.

“Hey! Watch it there!” she exclaimed with a giggle.

They all laughed good-naturedly. Ricky was laughing too but he was seeing this through different eyes. When he saw that boy kiss his girlfriend, he got a funny feeling and then it dawned on him that his petite girlfriend was the only girl there.

The guys each took another turn with the blindfold, stumbling and laughing and pushing each other as one boy bumped into another. When it was Connie’s turn to go again, the circle of boys seemed to tighten. Sure enough, she missed the donkey again and this time bumped into the Deke, the host.

“Ha ha! Missed again!” he bellowed as he put his big hands around her waist, pulled her to him and kissed her on the mouth as the other boy had done, only this time he held her tight against himself and the kiss lingered. This time, there was less laughter and the other boys were watching more closely. At a moment like this most guys would yell “What the fuck!?”, grab their girl and get the hell out of there, but Ricky found himself giggling nervously and saying “Hey, you two, knock it off.”

Finally, Deke released Ricky’s girlfriend and all the boys took turns pinning the tail again, but mostly seemed to be groping around looking for Connie. When it was Connie’s turn again she bumped into Mike. He grabbed her eagerly and kissed her as the other two boys had done. Then he started kissing her on the neck and reached up to slip the strap of her bathing suit down over her shoulder and caress her bare skin. Connie, feeling the vodka, just stood there and swayed unsteadily in his grasp.

“Is that you, Ricky?” she asked, unable to see who was kissing her.

“Would it be okay if it wasn’t?” asked Mike.

Connie pulled off the blindfold, pushed him away with a nervous laugh pulled the strap back up and said “Cut it out you guys.”

“Hey, hey, hey!” Deke chanted. “Mikey’s getting brave! Hey, Ricky, tell us what was going on down at the beach last weekend! I had no idea Connie was such a hottie!”

**********************

Soon the boys stopped taking turns and just urged Connie to keep trying. The paper donkey was no longer the target. Impaired by the blindfold and vodka, Connie just groped her way across the circle of boys, not knowing who she would find. The lucky fellow would kiss her and run his hands over her body.

“Hey, cut that out!” she would laugh as she pulled up the blindfold to see who was molesting her, but with every turn she took, she let the embrace linger a little longer and the kiss would get a little deeper.

When she finally bumped into Ricky again he too held her and kissed her.

“Are you okay?” he asked. “It looks like you’re enjoying this.”

She pulled him aside to whisper in his ear as the other boys took a break to get more beer.

“It looks like you’re having fun too — maybe a little too much.” she answered. “Look at you! What’s this!?” she exclaimed as she felt the front of his pants.

“I don’t know,” he mumbled. “This is kinda hot.”

“What? You like watching these boys kiss me?”

“You seem to like it and it turns me on a little to see how much all these hotshot jocks like my girlfriend. It makes me proud of you. Let’s play a little more and then I’ll take you down to the beach.”

“You want to go swimming at this hour?” she teased.

“No, silly. It’s tuning me on watching you tease these guys and I need to get you alone.”

“Well in that case. Maybe I can turn you on a little more.”

They went back to the circle of boys and Connie exclaimed: “I guess it’s my turn again!” and looked over at Ricky with a knowing grin.

“Alright!” the boys exclaimed, almost in unison.

Ricky helped her with the blindfold and whispered into her ear: “I had no idea my girlfriend was such a bad girl.”

“I like being bad for you,” she replied.

She bumped into Mike again. Emboldened by Connie’s willingness to continue, as he kissed her and felt her open her mouth for him he took her by the shoulders and pushed both her suit top straps down. He then bent to kiss her throat and chest just above her nearly-exposed heaving breasts.

“Oooo! You better stop that!” she laughed as she finally pushed him away but neglected to pull her straps back up.

There was the buzz of sexuality in the air as she prepared to go again. This time she bumped into Deke. Deke held her tight and kissed her and probed her now-welcoming and open mouth with his tongue. He then bent to kiss her chest as Mike had done but didn’t stop there. As he kissed her he used his thumbs to work the cups of her suit down to expose more and more of her smooth heaving breasts until her amazingly big, stiff, brown nipples popped into view. Surprisingly, she didn’t pull away right away and just held his head and moaned a little as he licked one of the rubbery buds.

“Oh my God! Look at these tits!” he exclaimed.

“You better cut that out!” she giggled as she finally pushed him away and took off the blindfold. “Deke! It’s you! You’re such a bad boy!” she laughed as she pushed her cups, but not the straps, back up.

***************************

At the other end of the basement behind a door that no one noticed stood Deke’s older brother, Donald. Donnie was living in the basement after he barely graduated from the local community college. With no job or friends, he spent his days on the computer playing violent video games, watching porn and writing nasty comments on erotic story websites. As he peeked through the crack in the door he diddled his little nub of a penis that was sticking out of his dirty boxer shorts below the flab of his hairy, sweaty belly. As soon as he saw Connie’s tits exposed by one of the horny boys, his spluge dribbled out of his stiff little dick and spattered on his flip-flops. He closed the door and went back to his computer.

***************************

On her next turn, Connie bumped into Ricky.

“How do you like your bad girl now?” she asked as she reached down to feel for the erection she hoped would be there. “Are you ready to go now?”

“Just a little more,” he whispered back.

“Okay, but be careful what you wish for!”

This time she bumped into Jon again. Jon was the youngest and least experienced of the group. He put his hands on her hips and kissed her tentatively. Connie stunned the group when she reached up and guided Jon’s head down to her tits and eased the top down herself. She resumed moaning as Jon nuzzled her as he had seen the other boys doing.

“Oh, shit!” he exclaimed suddenly as he put his hands down over his crotch and, red-faced, headed for the door.

“Ha ha!” laughed Deke. “I guess Jonnie doesn’t know how to handle a real woman…but I do.”

Ricky began to wonder if maybe Deke had done something like this before.

***************************

Deke stepped over to Connie who was still standing there with the blindfold on and her top down. He took up nibbling on her now-erect nipples where Jon had left off and she was soon cradling his head and moaning again. He stopped licking her long enough to unhook her top and throw it on the floor. He guided her to an old sofa that was up against the wall in a dark corner of the room and helped her to sit down. He sat next to her and, seeing what was happening, Mike sat down on her other side. Ricky was stunned, but watching silently. Sensing no resistance, Deke forged ahead. He kissed her neck as he reached down to fondle a breast and tug gently on her hard nipple.

“You’re a beautiful girl, Connie,” he whispered hoarsely. “Ricky’s a very lucky guy, and you’re a good sport.”

Not wanting to be left out, Mike moved closer to her and she jumped a little as she felt a new hand grope her other breast.

“Look at this. So beautiful, so hot. Look at these nipples,” continued Deke. “So tell me, Ricky, what was really going on in the car down at the beach?” as he kept fondling and tweaking her pert breast.

Ricky snapped out of his trance. “Oh, nothing. You know, fooling around.”

“It didn’t look like fooling around to me. It looked pretty serious. Was Connie going down on you?”

“Uh, yeah, she was,” Ricky mumbled as she watched his sweet girlfriend let these two jocks have their way with her tits.

“Does she like doing that?” he asked Ricky, but was really asking her as he moved closer and talked softly into her ear.

“Yeah, I guess so,” Ricky croaked.

“Is that true, Connie? Do you like doing that?” he asked her a little more aggressively. “Come on, you can tell me. I won’t tell anyone.” He continued gently pinching and twisting her nipple.

“Yes,” she whispered softly, the alcohol and the stimulation of her breasts making her whole body tingle.

“Is that so?” asked Deke. “Does she do a good job, Ricky?”

“Oh, yeah! She’s the best!” blurted Ricky proudly, forgetting for a moment where he was and what was happening right before his eyes.

“No kidding? Maybe she would like to demonstrate. What do you say, Connie? Would you like to show us what you can do?”

This was getting out of hand. This was way more than anything Ricky thought might happen. He was torn between wanting to rescue Connie from this situation and some twisted desire to satisfy some deep secret craving to watch his innocent little girlfriend do something very naughty. He was conflicted, knowing that all of this was outside the bounds of normal behavior, but he couldn’t help himself as she watched her sitting there blindfolded and topless letting two strong, healthy young men molest her.

“Ricky??” she pleaded and he was not sure if she was asking for help or permission.

Ricky was at the moment of truth. He could rescue her and bring a halt to this whole bizarre enterprise, or he could encourage her and see something that would feed, if not satisfy, something dark lurking inside him.

“Maybe just a little,” he mumbled. “You guys won’t tell anyone, will you?”

“Okay, just a little,” she said softly.

“That’s a good girl,” said Deke. “You ARE a good sport. What happens here stays here. Hey, I have an idea! You keep the blindfold on and we’ll all sit here. See if you can guess who is who. Here, let me help you up. Ricky, you get that pillow.”

“All of you??” she asked, incredulous.

***************************

Ricky stepped up behind her, put his arms around her and whispered. “Just a little. Okay? It will be hot. You’re so good and you know you like doing it. It’s not like it’s sex or anything. We’re just fooling around. Then, I’ll get you out of here. Here, kneel on this.”

He put the pillow on the floor in front of the middle seat and sat there with Deke on one side and Mike on the other.

“Oh, that’s good ,” said Mike. “Start with your boyfriend and that will get everyone warmed up.”

Ricky was feeling nervous for his petite girlfriend, kneeling there in her blindfold before three horny young guys and not knowing exactly what to do.

“Um, Ricky, she can’t do anything if you have your pants on.”

Ricky looked over at him and then nervously slid his swim trunks down to his knees letting his average-sized penis pop up.

“Uh-oh! Boyfriend’s got some wood there!” exclaimed Mike. “He’s getting into this!”

“Here, scoot forward,” Ricky said to Connie as he reached out to help her.

Connie put her hands out to hold his knees, feeling her way as she moved forward.

“Push these down,” she suggested helpfully as she tried to approach and get between his legs.

Ricky pushed the trunks down, kicked them off and opened his legs for her. She inched forward, taking the pillow with her. She felt her way up his thighs, took the base of his cock in her small hands and without further ado bent forward to take him in her mouth.

“Oh, shit!” Ricky inhaled as he felt her warm lips and wet mouth on his cockhead.

As Deke and Mike watched with great interest she nibbled and licked the head for a minute and then took more of him into her mouth and started slowly bobbing up and down. Ricky spread his legs further and reclined back into the sofa and watched with admiration as his girlfriend went to work. Connie increased her tempo and Ricky stretched out his legs and started to raise his hips. Soon, he was thrusting those hips in time with the bobbing of her head.

“Oh! Oh! Oh, shit!” moaned Ricky.

Just as Ricky was about to pass the point of no return, Deke intervened.

“Okay! Stop! That’s enough there, Connie. We don’t want Ricky here to get off too soon or he might snatch you away before the rest of us get a turn. Okay, we’re going to play a different game now. Musical chairs. Switch places, guys.”

***************************

Mike and Deke stood up but Ricky was reluctant to move. While he hesitated Mike and Deke shot rock-paper-scissors to see who would go next. Mike won, but with the blindfold still on, Connie had no idea who it was.

“Come on, Ricky, move over. You can get more later,” commanded Deke.

Ricky finally moved over and Mike took the middle seat and sat before the kneeling Connie. He kicked off his swimsuit as Ricky had done. He was also fully erect and his hard cock was about the same size and shape as Ricky’s. Connie leaned forward from her kneeling position on the pillow and ran her hands up his muscular thighs. One thing that was different about Mike is that he was manscaped. In those days it was not unheard of for a woman to shave down there, but apparently Mike was something of a pioneer among men. When Connie’s fingertips reached his dick she noticed the difference right away.