NOTE: This is my entry in the Literotica Valentine's Day Contest, and it is a tale of loving sex between two gay men who have formed a stable relationship in San Francisco's Castro District. If stories about this kind of activity disgust or irritate you, you should probably stop reading now.
Paul Porter, known to most friends as Pauletta, loves his life as a drag queen in San Francisco's Castro District, but there have been some aspects of it that were less than perfect. Although he has enjoyed many great sexual escapades with a variety of men over the last few years, some of them several times, until this year, he had never received any token of affection on Valentine's Day from even one of those men.
It wasn't that he had gotten a lot of romantic attention from people while he still lived in his home town. None of the girls of his acquaintance had ever been physically attracted to him or thought of him as a love interest, although he had several close female friends. "Paul is sweet, but just not my type," was generally the attitude of the girls he knew then, regardless of what the "type" of one of them might have been.
He had never sent or delivered to any of them a valentine or made any other special gesture of affection either, because none of the girls interested him sexually or romantically. Some of the boys did, but he learned early in his life to keep that fact from them and the girls and everybody else, or suffer dire, possibly even fatal consequences. Therefore, throughout his youth, he had never received a valentine from anybody except older female relatives, nor had he ever given one.
This year, he expected things to be different. Instead of carousing with a variety of sex partners, he has a steady man sharing his apartment and bed. Pauletta really likes Cliff, a large, affectionate man of the type usually thought of as a bear, besides immensely enjoying the sexual activities they share, and he was hoping that would be the year he received his first valentine ever.
On Tuesday, February 14, they got out of bed at the usual time and began their preparations for the day. There was no sex, outside of some kissing and fondling, because they both knew they had to get ready for work. After eating a healthy breakfast of fruit and toast and coffee, Pauletta showered and shaved and dressed himself in the khaki pants and one of the sport shirts he usually wears to work. He bound his long blonde hair in a ponytail and left for his job at the high tech company where he works on the order desk. Cliff is due to arrive at his job later in the morning, so he completed his preparations, personal and otherwise, after his partner left.
Just as Pauline was hoping to finally receive a valentine that year, he was also looking forward to giving one. On his way home, he stopped off at a shop that specializes in gay and lesbian valentines and picked out one specially designed to give to a gay man such as Cliff. It portrayed a large, hairy grizzly bear with a friendly smile and with his arms spread to wrap somebody in a big, affectionate bear hug. To Pauletta, it was the perfect valentine for his lover, and he hurried home with it, eager to present the card to its intended recipient.
He was surprised to see Cliff had gotten home earlier, and met him at the door to their apartment. As they usually did, the two men shared an embrace and a kiss, before the big man made an offer Pauletta could not refuse.
"I have dinner reservations for us at Frances. We can drive there and stop at The Purple Knight for a drink on the way back here. You already know what'll happen after we leave The Knight and come back here."
Pauletta did know, and he quivered in anticipation. "Do you want me to get dressed?" he asked, grinning because he already knew the answer.
"Yeah, go ahead. You know I like it when you're dressed. Of course, we'll get nekkid after we come back here."
The young blonde grinned lewdly at that indecent proposal and, after removing his shoes, went into the bedroom to change his clothing to the feminine attire he favors when he was in drag. Pauletta had been surprised at seeing his lover in the apartment when he got there, but he was amazed when he beheld what Cliff had done before that arrival. A fastidious housekeeper, he had made the bed before leaving that morning, but it had later been remade in a particularly enticing fashion.
Instead of the usual white sheets, the mattress was covered with a pink fitted sheet, obviously new, and the top sheet, also pink was folded down to make the bed ready for them to use. Leaning against the headboard were two pillows in brand new crimson satin cases, either of them embroidered with a pair of white hearts connected with a white arrow that pierced them both. His name was embroidered under the hearts on one of the pillows, and "Cliff" was in the same place on the other. The dear, sweet man responsible for the surprise came up behind the recipient and put his arm around Pauletta's shoulders.
"Happy Valentine's Day, Sweetheart. I hope you like it."
"Like it? I LOVE it. It's the nicest and the sweetest thing anybody has ever done for me." He threw his arms around Cliff and planted a big, wet kiss on his lips.
"I got a valentine for you too. It's not much, compared to this, but here it is." Pauletta took the envelope containing the card out of the plastic bag he had been carrying and handed it to the man who had just given him the most wonderful valentine he had ever seen or even ever heard of.
Cliff opened it and smiled at the sight of the cartoonish bear. He grinned and spread his arms in imitation, and Pauletta stepped into the embrace to share another kiss. This time, their tongues also greeted each other, and he could feel his cock stiffening and his ass twitching in anticipation of what they would be doing on top of the elaborate valentine he had received from Cliff.
"Do you want to try out the bed?" Pauletta asked.
"Of course, but not until we get back from dinner. There's no real hurry, but they won't hold our reservation open forever."
He had to agree that was so, but Pauletta decided to give Cliff a preview of what would be his in a few hours. He turned his back on the big bear, not as a snub but so he could put on a little show. It began with Pauletta unbuttoning his shirt and tossing it aside, showing off his slim build and fair white skin, well aware that was something the big man liked to look at. Next, he went to the closet and picked out a matching panty and padded bra set, one of those he buys from Fredericks of Hollywood. He turned to Cliff then.
"Hey, Big Boy, do you want to hook my bra for me?"
Pauletta could have done that by himself, but he knows Cliff likes to do little things like that for him. He turned his back again and held the bra cups in place while the bear hooked the catch in the back. The show resumed when he unbuckled his belt and shimmied his hips to let his pants slide down his smooth white legs until they formed a puddle around his ankles. Pauletta's red jockey shorts quickly followed, helped on their way down by a slow bump and grind of his hips.
Cliff was almost mesmerized by the cute naked white ass in front of him. He had seen it many times, but could never get enough of the sight of its smooth skin and succulent curves. The view got even better when Pauletta bent over and pulled his socks off, putting on even better display the place where Cliff's cock, which was fully erect by that time, would be in a few hours. He couldn't hold himself back; the bear stepped up to the sexy display, placed his hands on Pauletta's soft hips and pulled the object of his lust against his crotch.
"Oooo, you're a fresh guy," Pauletta teased him. "I like fresh guys."
"Vixen! You know you're driving me wild, don't you?" As he spoke, Cliff rubbed the soft white ass against his crotch, letting Pauletta feel the stiff result of his coquettishness.
The teasing man reveled in the attention as he finished removing his socks and lifted his feet to finish pulling off the rest of his clothing and toss it aside. Bare naked, except for his bra, he straightened up and reached back to fondle Cliff's hard cock through his pants.
"Oooo, I really like fresh guys who have what you've got here," he murmured, turning around to flash his most lascivious smile at the man he had just aroused.
The show was over, at least until the encore performance that would occur when the two men returned to the bedroom, but Cliff watched as Pauletta stepped into the panties which, he knew, were crotchless. Next, he selected a sheer blouse, soft pink in honor of the occasion, which he would put on after applying his makeup. With his face ready, he donned the blouse, followed by stepping into a red miniskirt. The walk to where Cliff parks his car was a short one, but the mid-February night was cold, so he would need to wear the warm gray and black and white wool coat which was also in the closet. Just before leaving, Pauletta picked up his red purse and put on the matching red leather pumps he had placed next to the door. He prefers to go without stockings, and all the men he has had sex with, including Cliff, prefer his legs to be bare too.
Cliff works in a bank downtown, and he would continue to wear the charcoal gray business suit he had worn there.
Like most places in The Castro, Frances is not far from the apartment where they live, but the evening was already cold, and Pauletta doesn't like to walk very far in heels if he can avoid it. The drive took no more than ten minutes, and the wait to be seated was only another few minutes. They saw friends and acquaintances, and some of them waved, while others greeted them in passing, but nobody sought to join them. Being Valentine's Day, it was accepted they were a couple there for a romantic dinner, and not to be pestered by unwanted company. Those who did not know them left the lovers alone, for the same reason.
Pauletta enjoyed the Gulf Snapper with a glass of white wine, and Cliff ordered steak and a bottle of beer. Neither is a heavy drinker, because they enjoy life and each other too much to want to blur their perceptions. They both enjoyed their meal, partly because the food was good and partly because they were allowed to be together, which was what they wanted. After paying the bill, including a generous tip, Cliff helped Pauletta with his coat again, and they went to The Purple Knight to see and greet more of their friends and to show off each other.
"Hi, Pauletta. Hi Cliff," were the greetings they received when they entered the club. As he had been at Frances, Cliff was the recipient of many looks of envy because of the beautiful drag queen on his arm, and everybody there knew the two men were an item.
They didn't stay very long at The Purple Knight, because they both had to work the next day, and they were both hot for each other and eager to get home and to bed. Pauletta had a single glass of white wine and Cliff limited himself to one bottle of beer before they left the club, got into their car and drove home. His usual habit would have been to drive to the garage where he paid monthly for a parking space, but Cliff was so anxious to get home, he left the car on Castro Street, just down the block from the brightly-painted Victorian where the two men share the apartment. Pauletta's hand fondling his cock was another good reason for his being in a hurry to get home.
After Cliff had locked the car, the two lovers hurried to the place where they hoped to spend the next few hours doing what was natural. Pauletta had his keys out of his purse and in his hand by the time they reached the top of the front doorstep, and they wasted no time in closing the door behind themselves. In his heels, he had to be careful climbing the stairs, but they were the first things he removed once they were inside their love nest. Cliff took a little longer to sit down and remove his socks and black oxfords.
Barefoot, Pauletta stood in the doorway gazing wistfully at the bed which had been transformed into his lovely valentine. "It's so beautiful," he murmured, "and so thoughtful of you," he said to Cliff. "I hate take it apart. But I'd hate even more not using the bed."
"I know. Me too. That's why I took a lot of pictures with the digital camera."
On hearing that, Pauletta turned and hugged the big bear. He unbuttoned his coat and, while Cliff was shrugging out of that, removed his necktie. Although eager to get into bed together, both men took care of the clothing that needed care, with Cliff hanging up his suit and Pauletta making sure his wool coat was hanging on the back of the bedroom door, which was its usual place during the winter. With those things taken care of, they embraced beside the pink and white and crimson valentine bed and began removing the rest of each other's clothing.
Cliff finished with the blouse buttons first, and Pauletta turned around to let that garment be pulled off his shoulders and his bra be unhooked. Bare above the waist, he finished with his lover's shirt and pulled the undershirt off over his head, leaving the bear's muscular torso equally nude. Before removing any more of his lover's clothing, Pauletta moved in close and kissed the bulging muscles under their smattering of dark, curly hair. He loves the way the big man is built, and has no aversion to showing it.
Cliff was demonstrating his affection too, as well as his lust, reaching under Pauletta's skirt and fondling his succulent ass cheeks through the smooth fabric of his panties. Cliff's hands didn't remain on the outside very long, because he stuffed them through the waistband of the silky garment to fondle the bare skin, which was even smoother. With his hands still inside, he pushed the skimpy garment down and around the perfect ass it was covering, and Pauletta felt it sliding down his smooth, white legs. He wiggled his hips to help the panties on their journey. After kicking them out of the way, he unsnapped the boxer shorts before him and let them fall down to the floor, leaving Cliff naked, with his big, hard cock pressing against the man who was undressing him.
That man knew what to do about such a prodigious erection and, as the big man was stepping out of his shorts, he knelt on the floor and started licking the head of that cock. He loves the velvety texture under his tongue, and he licked all around, including the slit in the end and under the ridge. It was fun, but it was really just foreplay that night. Although Pauletta sometimes sucks off Cliff and masturbates while he does, he much prefers lying on the bed and getting his ass crammed. The other member of the couple feels the same way, and even likes to stroke his lover's cock during their fucking so they can both cum at the same time.
Wearing nothing but his miniskirt, Pauletta got to his feet and turned his back on Cliff, for the same reason he had done so before they went out. This time the show was over more quickly, because he just did a few slow bumps and grinds before his skirt slipped down his legs to the floor. He slowly bent over to pick it up, Providing Cliff with a good, long look at the ass he would be fucking in a few seconds, before hanging the garment over the back of a chair. Completely naked, or nekkid, he bent over again and, holding his ass cheeks spread, he walked over to the bed with the bear right behind, equally naked and sporting an even bigger erection than he's had a few minutes earlier.
They were so hot for each other no more foreplay was needed, but preparation of Pauletta's ass would be necessary. The sexy drag queen pulled the top sheet and all the blankets from the bed and knelt there on the mattress, which was covered just by the bottom sheet, hugging one of the heart-shaped pillows. He waited eagerly while Cliff went to the bathroom to get a small towel and a large one, and to the dresser to get condoms and the plastic bottle of Aqualube. Both men are tested regularly for AIDS and are otherwise confident of each other's health but, for aesthetic and sanitary reasons, they never go bareback. After Pauletta's ass has been fucked, he likes to suck the cum from his partner's cock, and disposing of a used condom is much easier than always showering right after sex and/or changing the sheets every day.
With Cliff crouching on the bed and his cock encased in latex, Pauletta reached back and spread his ass cheeks. Turning to his partner, he said "Hurry up. I've been looking forward to this all day."
"So have I, but we have to do this right."
He handed the large towel to Pauletta, who spread it on the bed where it would catch his semen when he reached his climax and ejaculated.
To Cliff, "Doing it right" also meant leaning forward and planting a big kiss on either of Pauletta's smooth white ass cheeks, followed by reaching between the lovely mounds and prying his cute, pink rosebud open with the fingers and thumb of one hand. The other hand held the bottle of lubricant, and he gently inserted the tip in the tiny hole he was creating and squeezed in a big dollop of the Aqualube. The man in front of him quivered in delight when he felt the cool, oily liquid gush into his most private area. Cliff set the bottle out of the way and continued with his preparations, which were as much fun for both of them as any other kind of foreplay would have been.
The next step in the process was especially delightful for Pauletta, and his ass squirmed in anticipation when Cliff inserted a middle finger all the way to his knuckle and spread the Aqualube evenly inside his partner's ass, massaging his prostate as he did. Pauletta cooed happily, as he always does at that point, and turned to his partner.
"Oooo, Cliffie, I really love it when you do that. But there's something I love even more, and you know what it is."
He did, indeed, know and, with the preparations of Pauletta's ass complete, he covered his cock with the lube and moved in closer. Still using the fingers and thumb of the same hand to hold open the lovely hole he was about to start fucking, he guided his cock with the other hand, until the tip was pressed against his target. After moving the tip up and down to begin the penetration, he thrust forward, sighing happily when he felt his cock wedge into the place he lusted for.
"Ooooo, yeah," Pauletta responded, and he writhed in bliss as a gusher of pure pleasure washed over his body. "Give it to me good," he urged his partner.
The urging was not necessary, because Cliff wanted nothing more than to give it to his lover as well as possible. He moved his knees slightly, and his next thrust forward drove almost an inch of his hard cock into Pauletta's eager ass, eliciting another murmur of joy. A few seconds later, almost two more inches burrowed its way into the tight, oily hole and was greeted with an even louder exclamation of happiness, because it was massaging Pauletta's prostate gland. There was enough of his cock inside that Cliff no longer needed to guide it, so he checked between his shaft and the opening that was stretched snugly around it to check for loose skin or any other possible problems. Finding none, he used the small towel to wipe the Aqualube from his hands and placed them gently on the soft hips of the man he was fucking.
Pauletta felt the hands and knew he was about to get his ass crammed, which was what he wanted. To present a better target, he bowed his back, raising his hips and lowering his face, which he pressed against the embroidered pillow he was hugging. The next time he felt the hard cylinder surging into his ass, he pushed back from his elbows and forearms and met the thrust. Most of the rest of the bear's big cock burrowed its way into him and, with a few more strokes like that one, he could feel Cliff's curly pubic hair against the sensitive insides of his ass cheeks.