Pauletta's New Boyfriend

One summer Friday night it was later than usual when Paul strolled into The Purple Knight with his blonde hair combed out into soft curls and wearing a dark blue miniskirt and light blue blouse. Under those garments, as he always does in that club, he wore a pair of crotchless blue panties and a matching padded bra, because he likes to always look his best and be ready for sex when he goes out in the evening. He had watched a special televised program after showering and shaving his legs and ass, which was why he set out later than usual that night. The bar was less crowded than most Fridays, but he still expected to pick up a man who would love to fuck him where his panties lacked a crotch and/or be sucked off or maybe even two men who would join him in the rest room for a romantic interlude.

Being well-known and liked there, he was greeted by almost everybody in the club, and they addressed him as Pauletta, the name he uses while in drag. He responded in kind and stepped up to the bar to order a small glass of white wine, his usual preference. The drinks there are overpriced, but nobody minds, because they consider their cost to be similar to an admission charge to a place where sexual pleasure is easily available. As he stood by the bar, a man he knew well joined him, holding a cocktail in his hand.

"Hi, Cliff," he greeted his friend and sometimes sex partner, and his salutation was returned.

The man who had approached him was just the sort of companion Pauletta was looking for. Besides being a large, pleasant young man, he is gay and strictly a top and is blessed with a big cock, which had been inside the drag queen's ass or mouth on several enjoyable occasions. Cliff was obviously interested in some sex too because, while the two men shared an embrace and a long kiss with their lips, he reached around and patted his new companion's curvy ass before ordering another drink.

"Oh, you're a fresh guy," Pauletta responded, while smiling. "I like fresh guys." It was what he said to everybody who fondled him the way Cliff had.

"That's good, because I like you too. I mean, I really like you."

As he spoke, the young top slipped his hand under the skirt of the drag queen and inside the opening in his panties where the crotch would have been and stroked the bare skin. Pauletta favors such under garments to give men easy access to his ass, such as Cliff was enjoying then, and so he can fuck in the men's rest room without removing them. The liberties being taken were much enjoyed by both men, and the recipient of the fondling arched his back to expedite the excursion of the other man's hand.

"Do you want to go into the men's room with me?" Pauletta asked.

"What I'd really like to do is go to your apartment for some hot sex and sleep in your bed with you tonight," Cliff answered, as his fingers slipped into the cleft of the ass he found so fascinating.

That took Pauletta somewhat aback. He had come to the club expecting to go to the rest room with somebody for a quick fuck, or maybe to suck somebody off. The management goes out of their way to make it easy for their gay patrons to indulge themselves sexually, and he performs one or both sex acts almost every time he goes there. He doesn't really care very much for morning sex, and he always removes his makeup before going to bed. Those are two reasons he usually preferred not to entertain overnight sex partners or be entertained by them, but he also has more than a little aversion to surrendering too much of his privacy.

At the same time, he was aware of how much better fucking is when lying face down or kneeling on a bed, as opposed to being on his feet and leaning over an open toilet, especially when his partner is a good and patient man such as he knew Cliff to be. Pauletta always has genuine affection for his sex partners or they would never reach that status, but he has always felt a special fondness for the man who was standing beside him. Cliff was starting to slip the tip of a finger into his ass, and Pauletta knew his cock would feel much better. If the suggestion had been to go to a motel, or some place such as that, it would have been turned down flat, but he would still be in charge in his apartment.

He made up his mind. "Okay, my place it is."

Cliff removed his finger from Pauletta's ass and the men finished their drinks and strolled to the door. Some who watched them go outside, instead of to the rest room were surprised, because they know the sexy drag queen's usual preferences, but nobody said anything, except to wave goodbye. Once outside, Pauletta started to lead his friend to their destination.

The Castro in San Francisco is a rather small part of a very compact city, and every place in the district is a fairly short walk from any other. Although rather late, it was still Friday night, so many of the denizens were out and about, and the two men had an easy walk from The Purple Knight to Pauletta's residence in a brightly painted Victorian. After unlocking the front door, he held it open for his guest and they walked upstairs to his apartment in the front of the building.

"This is a really nice place," Cliff remarked as he stood in the front room after Pauletta had closed and locked the door behind them.

Although small, the apartment is clean and well furnished and has a bay window with a view of the busy street below. Pauletta is proud of the way he had decorated the place, and wanted to show his visitor around, but Cliff had other ideas. He had already expressed as much appreciation as he was going to, at least right then, and had other things on his mind. Number one among those things was the shapely little ass he had been thinking about all day and had been fondling a few minutes earlier.

Paul is a slender man, and rather short, especially since he removed his high-heeled pumps immediately after closing the door behind himself and Cliff. His partner for the night is burly and over six feet tall with broad shoulders, just the kind of physique Pauletta finds attractive. They embraced, Cliff enfolding the smaller man in a bear hug and bending down to kiss the pretty, lipsticked face turned up to meet him. While their tongues explored each other, his hands did some more exploring, raising the hem of Pauletta's mini skirt and pushing through the elastic waist band of his panties to squeeze either of the soft cheeks available to him.

When he felt the hands on his ass and his panties being pushed down, Paul ended the kiss and grinned up at the large, eager man. "Oooo, I like that, but let's go into the bedroom," he murmured.

Still embracing, the two men sidled through the door and up to the bed. Once at that goal, Pauletta took over the removal of his panties, pushing them past his hips and shaking his legs until they slid to the floor so he could step out of them. While in drag, he never wears stockings, preferring to entice partners with his smooth, hairless bare legs which they love to stroke and he loves to have caressed.

He had returned to his apartment to have naked sex in the bed, so Pauletta pulled down the zipper on Cliff's jacket and, while his visitor was shrugging out of it, went to work on the buttons of his shirt. When his visitor turned around, he pulled it free, and gently massaged the muscular bare shoulders and back and sides in front of him. During their previous sexual encounters, neither of them had removed any clothing, and Pauletta saw what he had missed.

"You've sure got nice, big muscles," he murmured. "You're a real bear."

"That's not the only thing I've got that's nice and big."

"Oooo, I know." Pauletta reached around to unfasten Cliff's belt and unzip his jeans but, before doing that, he fondled the big, stiff cock that was straining against the denim.

Eagerly, he finished unfastening the pants and started to pull them down. "Turn around," Pauletta requested and, when the big man did so, he pulled the jeans down to his mid-thighs and pushed lightly on his chest so he sat on the bed.

Pauletta quickly knelt to untie Cliff's shoelaces and pull off his shoes and socks and drop them onto the floor, followed by stripping off his pants and tossing them onto a nearby chair. He reached into the fly of his guest's jockey shorts, wanting to pull his cock through to stroke it a few times with his mouth, but it was too big and hard to fit through, so he pulled the underwear down as he had the blue jeans, making sure the object of his lust was clear of the elastic waistband. Cliff was completely naked, and Pauletta moved in closer and raised his head so it was directly over the stiff cock that was so enticing.

Slowly, he lowered his face until he could reach out with his tongue and lick the head. As always, Pauletta reveled in the texture, like warm velvet, and his tongue stroked in concentric circles until he was licking under the hard ridge. While his tongue continued with the circles, he lowered his mouth farther, loving the feel of the hard, thick roundness spreading his lips. When the tip was pressing against the back of his throat, Pauletta stopped and withdrew his mouth until just the head was nestled between his lips.

He repeated the same kind of stroke a half dozen times while unbuttoning his blouse and unzipping his skirt. Pauletta loves the feel of a big cock stuffing his mouth but, even more, he loves having his ass crammed by something like what Cliff had for him. After the preliminary strokes with his mouth, he looked up at the big man on his bed, smiled and stood up to remove his blouse and skirt, which he hung up in the closet. The pretty drag queen wears good quality clothing and takes care of it as well as he can.

Naked, except for the padded bra he would leave on, he went to the bathroom and returned with a towel and the squeeze bottle of Aqualube, which Pauletta handed to Cliff. Before lying face down on the bed with a pillow under his waist and his legs spread, he fastidiously spread the towel under where he would be lying. He expected to be cumming, probably quite a lot, and didn't want to have to either sleep in the sticky mess or take the time to change the sheet.

"Do you have a rubber?" he asked. Pauletta loves the sensation of a bare cock passing between his lips and squiring cum into his mouth, but he insists on practicing safe sex when he is being fucked in the ass.

"Right here," Cliff answered, and he went to get one out of his pants pocket and put it on. He also believes in safe sex, and keeps them ready when he expects to indulge in some.

Knowing his partner knew what to do next, Pauletta reached back to spread his ass cheeks when he felt the bed move as Cliff knelt between his legs. Seconds later, fingers and a thumb pried open his ass and he felt the tip of the squeeze bottle twisted into the tight hole being created. This was followed by a gush of cool oily liquid entering his ass and a long finger that spread the lubricant. It already felt so good Pauletta's body was squirming happily, and it felt even better when the thick, blunt head of a cock was pressed against the oily hole being offered to it.

Pauletta cooed happily when he felt the hard tip wedge its way into his ass, and his movements became more strenuous. With the next thrust, almost two more inches of Cliff's shaft drove into him, stretching his tight hole farther open and starting to massage his prostate. There was a brief pause, as his partner moved his knees closer, and Pauletta's shoulders were gripped by a pair of muscular hands. With the next thrust, almost all the rest of the hard cylinder burrowed into him, and the soft insides of his ass cheeks were being tickled by coarse pubic hair.

Cliff stayed in that position while his friend's body writhed under him, making it better for both of them. The inside of Pauletta's ass was like silk, and his cute buns were soft and smooth as pillows. As good as it was just lying there, he knew it would be even better when he was driving his cock in and out, so he slowly drew back, paused, and plowed in again, this time plunging it even more deeply. Pauletta moaned in delight as the big, hard shaft spread him open again and massaged his prostate, which he thought of as his clit. Once again, the two men remained lying closely together, until Cliff slowly drew back again.

This stroke felt even better than the first. "Oh, that's good," Pauletta murmured back to his partner. "Your dick is so big and hard."

"I'm glad you like it, because your ass is the best place it's ever been."

After those mutual compliments, the two men continued slowly and quietly fucking. There was no need to talk; their sighs and moans of bliss said it all, and the only other sound was the rhythmic squeaking of the bed under them. The lube had completely liquefied and was working perfectly. Pauletta's ass was just as snug as ever, but there was no friction, nothing but a sensation of a smooth, tight hole that massaged his cock as Cliff drove it in and out.

As great as it was for Pauletta, he knew of a way to make it better. "Let me get up on my knees, so I can fuck back to meet you," he suggested.

To Cliff, that sounded like a great idea, so he drove his cock all the way into his partner's ass and started getting to his knees, pulling him up at the same time. Pauletta pushed up from the bed and, when they were in the new position, Cliff was kneeling directly behind the pretty drag queen with his entire shaft still buried in Pauletta's ass and both hands on the succulent hips he was pressing up against. He gently fondled and stroked and squeezed his partner's thighs and, especially his ass cheeks, his hands enjoying the outside as much as his cock was enjoying the inside.

They stayed like that for a few seconds, before Cliff started to slowly pull back, until he could feel and see the head of his cock right at the entrance to the tight hole he was fucking. Still moving slowly, he drove his entire shaft back in. Pauletta felt the thick giver of joy surging into him, exquisite pleasure radiating out from its path, and fucked back to meet it. Once again, pubic hair tickled the insides of the ass cheeks of the happy young man.

That stroke had been great, and the next was even better. There was still no friction, and Pauletta's prostate was stimulated with that one too, as the long, thick shaft plunged into him and again when it was pulled back out. Cliff was getting some of the best fucking he had ever gotten too, from the internal muscles that gripped and released him as he drove his cock in and out. Both men were having a great time, and they wanted their pleasure to last as long as possible, so they moved slowly while sighing and moaning in joy.

Of course, Cliff wasn't the only one with a stiff cock. From the intense pleasure being given to his ass, Pauletta's had developed just as hard an erection as the one that was providing him with so much joy. He had been supporting himself on his knees and both hands as he fucked back to meet the thrusts into his ass, but he reached up with one hand, intending to start stroking his cock. His partner saw what he was doing, and reached out to push the hand away and start taking care of his friend's other need.

Cliff synchronized his movements, driving into his Pauletta's ass and stroking his cock at the same speed. With every thrust, all the way to his pubic hair, he pulled his hand toward his partner's body while Pauletta fucked back to meet him. When he drew his cock back, he stroked his hand forward. The erotic movements were still slow, because neither man was in a hurry to cum, but they could feel their climaxes building, and reveled in the feeling.

"Ohhh, that feels wonderful," Pauletta murmured, as bolts of pleasure rocketed all throughout his body from his cock and his ass. "The best. Keep doing that."

"I will. It feels great to me too. I just love your tight ass."

After that, neither man spoke for a long while, except for their soft sighs and murmurs of joy. Pauletta was the first to break the silence.

"Oooo, that's so good. I'm getting ready to cum."

"Me too." Cliff said nothing else that but started stroking his partner's cock and fucking his ass faster."

"Ah! Ah! AHH!" Pauletta trilled, as he felt his climax exploding. "Oh, god!" he joyfully cried as he ejaculated onto the properly-placed towel.

Cliff didn't slow down, because he knew his friend wasn't through cumming, and he hadn't even started yet. He continued plowing in his cock and stroking his hand until he felt Pauletta's body jerk and heard him cry out with pleasure two more times. His friend was through cumming, he knew, and he was no more than seconds away from his own climax. Cliff removed his hand, smeared with semen from Pauletta's sticky cock, placed it on his hip for better leverage, and began plowing harder and faster into the ass that felt so good and tight. After a few dozen more strokes, his own climax erupted, and a big burst of semen shot into his condom.

Cliff wasn't through with just one ejaculation either, and he kept fucking until another big gob spurted out, and knew he was done. He had been keeping Pauletta upright but, when they were both through climaxing, he let his friend fall forward and stayed with him, until they were lying in a heap. They stayed in that position for a long time, murmuring of what a wonderful coupling they had shared, while Cliffs cock partially softened and he carefully removed it from the place where it had given and received so much pleasure. He went to the bathroom to discard his condom and take care of other needs.

When he returned to the bedroom, Pauletta was waiting his turn, and entered the bathroom carrying the towel that had been under his body. He took longer than Cliff had, because he had to wipe all the semen from his cock and pubic area and clean off his makeup and brush his long, blonde hair and put on his nighty. Pauletta is a drag queen in bed too, and loves wearing soft, frilly, lacy women's sleepwear even when sleeping alone. When he returned to the bed, he realized he wasn't quite ready to go to sleep yet.

Cliff was naked and lying on his back and his cock, which wasn't even close to being soft, was sticking up into the air. Pauletta yearned to take it into his mouth, feel it become fully erect and suck on it until he was given a mouthful of hot cum. He hurried over to the bed, climbed on and knelt next to Cliff. One hand held the object of his lust and he leaned over to lick the head and under the ridge, relishing the flavor of the semen that still clung there.

When he had cleaned that off, Pauletta slowly lowered his face, engulfing the shaft, while his tongue laved what was in his mouth. One of his most favorite sensations is feeling a cock becoming fully erect and spreading his lips and filling his mouth. It's fun and gives him a feeling of empowerment. Cliff was no exception and, as he slowly stroked the bear's cock between his lips, he could feel it stiffening and swelling until it was as big and hard as it had been before being plunged into Pauletta's ass.

Once that had been achieved, the happy drag queen moved over so he was kneeling on the bed between the other man's legs and bobbing his head up and down while slowly stroking the rigid cock between his lips. He likes to watch his partner's face from that position, especially the way pleasure flickers across a man's face, and he knows they like it too. Cliff was certainly no exception that night, and he derived visual pleasure, as well as sexual thrills from the blow job he was getting. Nothing was as good as the tremendous pleasure Pauletta's lips and tongue were giving him as they stroked and licked his cock, but it was also a treat to watch his thick shaft moving in and out of the lovely, creamy-white face while the pretty blue eyes gazed at him.