Bobby in the Bar

Bobby Timble was excited for a change. People said college was a place where you could reinvent yourself, be anyone you wanted to be and Bobby was ready for that challenge. Growing up Bobby was always the nerd. His best friend Nick and him would sit at their lunch table alone; they were never invited to a party, never went to a dance, never kissed a girl. Bobby and Nick were both short and lean lacking the physique and coordination to be good at sports. They were both young and somewhat effeminate looking which did little to help endear them to their peers. But Bobby and Nick had taken advantage of their intellect and were now starting their first year at a prestigious university both believed that now was finally their time to shine.

Bobby and Nick had requested to live together in the dorms. Their request had been granted and the two boys would be sharing a triple in a large freshman dormitory. The third roommate was a boy name Jake. He was also on the petite and effeminate side though more toned, and certainly more confident than the two other boys. Bobby was glad that the three of them had quickly become friends.

It was only a few days after the year had begun when Jake came rushing into the room to tell Bobby and Nick that he had been invited to a party...by a GIRL. Even better he could bring Bobby and Nick. At first the boys were all excited but then Bobby's nerves began to get the better of him. He had never been to a real party. Certainly there would be alcohol at a college party and he had never had a sip; wouldn't he look like a fool. As he voiced his concerns he was glad to see that Nick and Jake seemed to share them. Still nerves or not how could they not jump on this chance to change their social situation.

The next day Jake suggested, "Why don't we got to a bar? Then we could drink and get drunk before the party so we would know what it's like and not seem like total losers at the party." The other boys agreed but being 18 and without a fake ID or any idea where to get one it seemed impossible for them to get into a bar.

"Well...I know this might seem kind of weird...see my brother's gay...that's not the weird part...but he's been to this gay bar Lancaster's and says—well you know how girls can get into bars even if their underage because it brings the guys in, well he says this bar is kind of the same way only with 'bottom boys,'" said Jake.

"What are bottom boys?" asked Bobby.

"Well, technically they're like the ones that get, well fucked, but my brother says this bar tends to cater to men who like their bottom boys young and pretty, kinda like us. So we could get into this bar probably...We wouldn't have to do anything right. A bar's a bar we could just go have drinks, right?"

The boys thought about it and it seemed reasonable. "What's the worst thing that could happen a guy hits on us," said Jake kind of laughing. So the boys agreed to head to the bar that night.

Jake had a car and drove them to the bar, which was about 20 minutes away from campus and in a pretty isolated part of town. When they arrived at the bar and headed to the entrance a big sign on the front said "Lingerie Night!" "What does that mean," asked Bobby pointing to the sign. Jake shrugged.

When they got to the entrance there were two lines one labeled "Tops" and one labeled "Bottoms." There were two large bouncers at the entrance letting people in, checking IDs, and handing out wristbands.

Bobby felt extremely nervous, he was sure that someone would realize they were frauds. "They're checking IDs," he whispered to his two friends.

"Not everyone's though," said Jake. "We just have to fit in; we'll be fine."

The boys approached the entrance and headed to the line marked "Bottoms." Bobby could see what Jake was talking about most of the boys did seem a little older than them but they were definitely physically the same type. He also noted that as each boy got to the front of the line they opened their coats to show the bouncer what they were wearing underneath. Bobby hoped he was dressed okay. He tried to wear what he considered "going-out" clothes but he didn't have anything that was much like that or very fashionable, certainly not clothes he would imagine someone would wear to a gay bar.

When they reached the front of the line the three boys approached the bouncer together. He looked them up and down in a very sexual manner that made Bobby uncomfortable. The boys opened their jackets. "It's Lingerie Night tonight boys," the bouncer said pointing to the sign. Bobby tried to think of something to say that would make him appear knowledgeable but all he could do was stare dumbly at the bouncer which seemed to be the same reaction his friends were having.

"It's a new thing were trying. So far everyone seems to like it. The bottom boys have to wear lingerie. Trust me it's pretty hot."

"We don't have lingerie," said Jake. Bobby was sure that this plan was going to turn out to be a disaster.

"Don't worry," said the bouncer leering at the three boys. "Tani will fix you up; my boss would never forgive me if I turned three boys as cute as you away." He led the boys into the hallway that led to the main part of the door and pulled them through another door before they go into the main part of the bar. "This is Tani she'll take care of you," said the bouncer before he left and shut the door behind them.

In the room was what appeared to be a girl putting on make-up at a dressing table. She turned around when she was introduced. "Take off your coats boys," she said as she went over to take the coats from the three boys. Her voice was somewhat deep for a girl, but Bobby was too naïve to pick up on the signs that Tani was not a real girl. "Any preferences? Teddies, tap pants, corsets, thongs? Colors, fabric, styles?" none of the boys replied to her. "Well I guess I'll have to use my best judgment. Have any of you dolls worn lingerie before?" The boys all shook their heads no.

Bobby felt like running. He didn't know much about lingerie but he knew it was skimpy and feminine. He didn't think he could bear putting it on and walking out into a bar, but his friends were not running and he didn't want to seem the only coward.

"You boys are absolutely adorable so whatever I put you in the men will be waiting in line to get into your pants, or perhaps more accurately panties." She thought for a moment. "I have three matching teddy and panties sets that will be just perfect on you." She turned around excitedly and rummaged through a drawer pulling out several pastel colored lacey confections. She handed a set to each of three boys and ushered them each into a dressing room.

Bobby stood motionless in the dressing room until he heard Tani prodding him from outside. He slowly took off his clothes and stood starring at the lacey pieces of clothing. "Hurry up darlings, Jake is already out and he looks just smashing."

Bobby slipped on the panties. They were blue and lacey and worst of all they were a thong. He then slipped on the semi-sheer blue lacey teddy that ended just bellow his bottom. He wasn't sure if he wished there was a mirror in the dressing room or not. He did want to see how he looked, though, he was pretty sure if he did he would never be able to get himself to leave the safety of the dressing room. Slowly he emerged to see Nick and Jake standing in provocative ensembles.

Before Bobby could wrap his head around the fact that he must look as scandalous in his outfit as Nick and Jake looked in theirs, Tani had pushed the boys into the bar and locked the door behind her. There was no going back.

The three boys headed to the bar to do what they came for. Bobby didn't notice the many sets of eyes that followed him on his path. The boys sat at the bar. Jake ordered them drinks, as Nick and Bobby had no idea what to order.

The bartender returned taking $12 from each boy plus tip for the drinks. "You boys are too cute to be paying for your own drinks. Those men over in the corner haven't taken their eyes off you since you sat down. I bet they would be happy to buy you your next one and trust me you can just tell by looking at them that they are big spenders."

Bobby looked over in the corner at the secluded booth. There sat three men who were much older than Bobby, looking to be in their early forties. They were muscular, manly, black, and were wearing what looked like expensive suits. One of the men caught Bobby starring at them and winked. Bobby blushed and quickly turned away.

Bobby and Nick were not comfortable at first with the idea of getting men to buy them drinks. But the drinks were expensive and they couldn't really afford to continue to buy them. After some prodding Jake convinced them to let the men buy them drinks.

Finally, Jake took the lead and led them over to the men in the corner. "Hey sexy," said one of the men pulling Jake into his lap the other men followed suit and soon Bobby and Nick found themselves each sitting in a man's lap. The men introduced themselves. Bobby was in Paul's lap, Nick was in Jerome's, and Jake was in Jamal's. The men ordered the boys another round of drinks and before Bobby even knew it he seemed to be nursing on his second beverage.

The more he drank the more he understood why people liked to drink. He felt more relaxed, more at ease with himself, everything seemed funnier...it was nice. Paul was clearly flirting with him and though he was not at all interested it wasn't the worst thing in the world for someone to be interested in him. He had never really had anyone think he was sexy before and it was nice for someone to feel that way about him, even if that person was a man. A compliment was a compliment, right?

As the drinks kept flowing and the night wore on Paul's flirtations grew. Suddenly the older man's lips were on his and he was being kissed. Paul's firm grip on him meant Bobby couldn't pull away even if he wanted to. But Bobby wasn't sure he did want to. It seemed incredibly embarrassing that he got his first kiss from a older black man but at this point that was an unchangeable fact, and besides drinking if all went well he would hope kissing would also be a part of the upcoming party. At least this was practice and would let him know what to do. Though, a small part of him was saying that this was very much a man's kiss, no woman would kiss him with such possessive dominance. Paul's hands wandered down to Bobby's ass and kneaded as the kiss continued. Then the kiss was over and Bobby was left panting, breathless, and embarrassingly a little hard. He looked over and it seemed Nick and Jake had suffered a similar fate.

The night continued and Paul kept telling Bobby how sexy he thought he was. It seemed all the things he hated about himself, his short stature, thin frame, and feminine features, were the things that Paul found so desirable. Though, Paul did seem fixed on Bobby's behind, which if Paul was to be believed, was especially round, firm, shapely, and appealing.

Before Bobby knew it he was being drawn into another kiss, though this one was longer, wetter, and deeper, and if possible, more dominant and possessive. Once again Paul's hands sneaked down to Bobby's behind, but this time one finger pulled the back part of his thong aside while another slipped between Bobby's cheeks and began stroking his puckered rosette. This strange feeling on such a private part of Bobby's physique caused Bobby to jump, and if Paul hadn't had a strong hold on Bobby, Bobby would have jumped right out of his lap. Paul removed his finger and Bobby breathed a sigh of relief believing his reaction had stopped Paul from continuing, but he was wrong. A moment later Paul's finger returned this time wet and slick and began to slowly slip into Bobby's ass. Bobby squirmed trying to escape the finger but Paul was too strong and persistent. He couldn't protest because Paul's tongue was deep in his mouth. The stretching of his hole hurt slightly and was embarrassing, but there was nothing Bobby could do about it, and it seemed that Paul did not notice or did not care about Bobby's struggles. The finger continued burrowing in and soon the whole finger was inside Bobby. The finger felt so big inside Bobby, and for a few moments it just sat there unmoving. Then it started to move. At first it didn't feel like much to Bobby, just strange. It didn't hurt anymore but all of a sudden it hit something, something that felt so good Bobby moaned into Paul's mouth and once again almost unseated himself from Paul's lap. Bobby felt an answering chuckle in his mouth.

Paul continued to finger him seeming to hit that spot with every thrust. It felt oh so good to Bobby. Each time felt better and better. Bobby was gasping into the kiss, his penis was hard as a rock, and without intending to he could feel his ass slowing moving back to fuck itself on Paul's finger. Bobby couldn't think straight it felt so good, and before he knew it his head fell back, he let out a long moan, and came hard into his panties.

After a few moments Bobby recovered and looked over at both of his friends similarly engaged with their men. Bobby's face was bright red and was glad his friends had not seen how much he was enjoying himself. It was good Bobby didn't turn around because he would have seen the group of men behind him who were clearly enjoying the show.

"You're such a little slut," Paul whispered into Bobby's ear and if possible Bobby blushed even more. "Look you're so wet from my finger in your pussy." Bobby looked down and could see a tell tale wet spot at the front of his panties. "When you stand up everyone is going to see that you jizzed yourself from being played with by a big black man." Bobby didn't know what to do. He didn't want everyone to know that he liked being played with by a man.

"Why don't you come upstairs with me? Maybe I can find something for you to change into. You can tell your friends you need to use the bathroom." Without even thinking Bobby agreed. His friends seemed to buy the story and decided to join them upstairs. Bobby was thankful that Paul walked upstairs with him in a way so that no one could see his incriminating spot.