A Closet Homosexual

"Well, we've gone our separate ways, got divorced a while back," Ben told Robert. "So, you're 'bachelor-ing' it," Ben said, changing the subject. "It's Friday night. Let's go get a beer and a bite to eat. You're a free man for a while. Baldwin's Pub is just down the street."

"Oh, I don't know. I'm not sure," Robert hesitated, knowing it would delay his plans of trying on his new shoes and dress.

"Come on. Wife's away. Let's go grab something," Ben pressed. Robert was not really an assertive type, so Ben's persuasiveness won out. He could put off his fetish for a while and in truth he had missed lunch only having snacks because of his thrift store shopping foray, so he relented and accepted the invitation.

"Okay. Let me call the wife and touch base. I'll meet you there in a few," Robert said.

Baldwin's Pub was a neighborhood sports bar, nothing fancy, just decent food and drink, a local hang out. Having something to eat and a few beers hit the spot, made him feel better and the beers loosened him up. He could delay his "date" with porn, lingerie and his hand till later. He still had more than a week to himself to fool around. Ben was bigger, taller, beefier than Robert, maybe 6'2" and 210. A little bit of a belly, but not much. Ben's personality was bigger too. More outgoing, more outspoken, but funny and easy going. He struck Robert as a bit lonely too, perhaps. Possibly that was why he sought Robert's company when they ran into each other, and he implored Robert to join him. It was all good, and Robert knew he was minutes away from his "special place" alone at home as they settled the tab and walked out together to the parking lot.

"Come on over for a drink if you like," Ben then pressed again.

Robert had two beers over dinner and almost ordered a third, but thought better of it. By now the luster of his crossdressing plans had worn off and he knew it would not be as fun or as dramatic as the night before. He was tired from staying up late for the crossdressing and masturbations and did not get the best night's sleep. He supposed by now another drink was OK and then he could pick up on his crossdressing and masturbation in the morning, it would be Saturday and he'd have the whole weekend to himself.

"Okay, but just one," Robert told Ben. "Just one, otherwise I might get tipsy," he went on, kidding absentmindedly.

"Great," said Ben. "Just want to clear things up, up front. Just so there is no misunderstanding. I'm gay. You know that, right?"

No, Robert did not know that. Did he miss some signs? Was he that naïve that he couldn't tell? Certainly nothing in the way Ben acted and came off or in his mannerisms seemed the least bit gay. Just an average guy. Certainly nothing Ben did the entire evening could even remotely be construed as coming on to Robert. He looked at Ben with a blank stare. Nothing in the world made him think that he might be in this situation, that after all the past few years of chronic masturbation to gay porn, that a situation like this might arise. Robert's mind was racing.

Just the stark admission from Ben that he was gay shook Robert's world. Regardless of his fascination with gay, twink and sissy porn, regardless of his freedom now to cross-dress and saturate his psyche with femininity and homosexual desires, never did he contemplate seeking a gay encounter of his own outside of his quite stable marriage to Emily.

All the porn and masturbation and now crossdressing was a fantasy obsession, but he never had any intention to act upon it. He had panties on underneath his male clothes and the high heels and dress in his car from the lunchtime shopping foray. His toes were painted red from the night before. Finding this out from Ben made everything in his mind go blank with indecision.

"I understand if not," Ben offered. "I've always wanted to get to know you, you've always seemed so nice. Didn't mean to scare you off," Ben said apologetically like he was sorry to reveal what he did. "Maybe some other time," Ben said as he turned to go to his car.

"Wait. I can use a drink. I'll follow you there," Robert replied, not really knowing what he was getting into and not thinking that anything might transpire.

A myriad of scary feelings raced through his mind as did a profound sense of stepping into a strange separate reality. As Robert got into his car to follow Ben to his place, that funky scent that permeates thrift store clothing filled the air inside. Once over at Ben's there was a tentative nervous atmosphere about them, like not knowing if the revelation Ben made about his sexuality would lead to anything. In a situation like this where one person was up front about being gay and the other person hid his gay longings from everyone, when an opportunity like this presents itself, was it more than likely something sexual would happen?

"Scotch, bourbon, vodka?" Ben inquired as they stood nervously in the kitchen.

"Bourbon," Robert answered. Ice clanked into the glasses. Ben fixed himself a Scotch after fixing a bourbon for Robert. They set their drinks on the coffee table and sat an appropriate distance apart.

"Well, this is awkward," Ben softly said after taking a sip of his drink. "Thank you for coming over. Things are pretty quiet around here most of the time," he went on, confirming Robert's sense that Ben was somewhat lonely.

Ben talked a bit about his business and how it was doing, how he got started in it. He talked about neutral subjects, just not about the elephant in the room. They finished their drinks and Ben fixed another round. Straight bourbon and straight Scotch. Both were feeling pretty mellow. After some more innocuous conversation Robert broke the ice:

"What happened with you and Linda?" he asked. "Was it because you are gay?"

Robert asked this question because of everything he felt, all his masturbations to gay porn, his sexual encounters with other boys his age before dating Emily. These things he knew were inside him were relevant being married and trying to live a straight life now talking with an acquaintance who is divorced and out as gay.

"Pretty much," Ben said, making Robert cringe inside knowing he could very well be in the same spot if he came to grips with his homosexuality and if he ever came out.

Ben went on telling Robert how he felt inside being married and knowing that he was probably gay. He told about sneaking around having affairs with other gay men, how exciting the sex was but how guilty he felt hiding it from Linda. Robert asked how he broke it to Linda or how did she find out. Robert was hard as stone when Ben relayed the details of coming out and getting divorced.

"I'm sure I'm boring you with all of this" Ben said as he finished his second drink, Robert's was already finished. "Another drink?" Ben asked, getting up to fix a third one.

"Sure," Robert said handing off his glass with each male giving the other a somewhat questioning look, like "what does this all mean about the 'here and now'?"

Ben fixed another stiff drink for both of them and sat down after handing off Robert's drink. Both took a pull on their drinks, and it was quiet in the room with no TV or music on. They both had a pretty good buzz going. They looked innocuously into each other's eyes. Ben had no idea what was going on inside of Robert who had been questioning himself if he was gay the whole time sitting with Ben. Ben liked having someone to talk to. He was wondering if he'd have to put Robert up in the spare bedroom because of all the alcohol. Just as he was about to ask Robert that, Robert spoke:

"Know what?" he asked looking straight ahead and not looking at Ben. Before Ben could answer, Robert repeated "know what?" looking shyly at Ben, who shook his head not knowing where this was leading, as Robert then looked back straight ahead away from Ben.

Robert set down his drink on the coffee table and then slipped off his shoes. Looking coyly over towards Ben, he pulled off his socks and put his feet on the coffee table. The bright red nail polish on Robert's toes glistened pretty.

"Know what? I think I'm gay too," Robert blurted out. "Pretty sure of it now."

Ben's turn to have no idea, no inkling this was about to be revealed. Robert then slid his shoes back on and stood up, the socks still in a pile on the floor.

"Be right back," he said as he went to the door and out to his car to retrieve the bag from his noontime shopping trip.

As he slipped back in, he excused himself and went into the bathroom. Disrobing, he was then in nothing but panties and he pulled them down and sat down to pee. Admittedly, he was a little drunk. Pulling the panties up, his penis hardened a bit as he then sat on the floor, curious to try on the pair of high heels. It was drunken excitement that the shoes fit, perhaps not all that well, but they fit as he stood up and wobbled around in front of the mirror. He loved the way they made him feel. He loved seeing his red toes in the high heel sandals, it gave him a newfound thrill. Being in nothing but panties gave him the sense of femininity that he had loved all his life. Now in panties and high heels, his sense of femininity soared. It gave him a new sensation of gayness.

Trying on the burgundy cocktail dress, it felt fabulous. In the past when he had the opportunity to put on a dress it always sent his spirits and libido soaring. Just the sensation of femininity wearing a dress as it fluttered about his body gave him naughty, forbidden sensations that "normal" males aren't supposed to have. Straight males do not wear dresses. But males who love being feminine for other males do. Nothing can ever compare to the sexual stimulation of presenting yourself as femme to a masculine male while wearing a dress.

The dress looked and felt incredible on Robert; he had a slender physique and boyish looks that with proper makeup and wig he could be more than passable, even with no breasts. And being in high heels wearing a dress was just about tops for any crossdressing he had ever done. As a teenager he had worn lovely dresses of his mother and pretty sister and masturbated in them when they were not around. Emily did not wear dresses that often but there were a few of hers that fit Robert quite well on the off chance he had time alone to wear one and masturbate. But something about the funky thrift store smell made him want to take it off, he did not want to spoil the mood with that lingering scent.

Robert liked being nearly naked in panties for other males earlier in life. He had done it more than a few times, many, many years ago. The high heels gave the feeling of being in panties a remarkable new sensation. As he looked in the mirror at his slender hairless body wearing the bright pink panties with the stunning orangish pink trim, he knew. He knew he was about to reveal his homosexuality to another person after it had been locked up all these years. As he turned the handle on the door and pulled it open, all his demons were chattering with excitement, clambering and pushing each other and squealing as the door to their cages swung open and they bolted to freedom.

..............

Robert's latent homosexuality was established early in his sexuality, while still in school before he dated Emily. He and his sister Beth were raised by a single mother, he had never known his father. In his life he never had a positive male role model, no uncle or stepdad or family friend, only an occasional teacher at school. His mother raised him well, he was a good kid, but she worked two jobs to make ends meet and was not around as much as she would have liked. She babied and doted over Robert as much as she could and gave a loving home to him and Beth.

His sister was one year older and pretty like her mom, Robert was 'pretty' too in a boyish feminine way. Like any teenage boy his sex drive blossomed as he grew up and was infatuated with his pretty older sister and all the hottie girls at school. Rarely, however, did the girls at school pay him any attention as all the hot girls gravitated to the macho athletic types, which Robert certainly was not.

Teenage boys always seem to have a best friend, and sometimes these friends are quite opposite in nature and appearance. Robert was a clean cut 'pretty boy' type, and his best friend Jeremy was a bit of a 'goth' emo type with black moppy hair and piercings. Robert's mother did not particularly approve of his friendship with Jeremy. She knew Jeremy's mother and father and that allayed her concerns to a certain degree.

It was not uncommon for the boys upon occasion to spend the night at each other's house on Friday or Saturday night. Nor was it uncommon for the two boys to be at some point in their underwear with each other, getting ready for bed or in the morning or even just playing video games. Jeremy wore plain "tightie whities" while Robert would wear colored briefs with designer names like Armani, DKNY or Calvin Klein. Some of these colored briefs looked very similar to girls' panties. It was late one Friday night with Robert in bright yellow briefs with a red band and Jeremy in his whites that Jeremy pulled out some girlie magazines he had snuck from his older brother. Perusing the magazines with the pictures of naked girls made both boys very hard.

That night, in the aura of heightened arousal, Jeremy pulled his penis out of his underwear and began jacking off in front of Robert. He told Robert "It's okay, go ahead. I won't tell anyone, it's our secret." Both boys masturbated to ejaculation and Jeremy got a towel for them to wipe up. It was perhaps a bit awkward afterwards, but still an exciting event in their friendship.

Late night masturbations would continue to take place at Jeremy's house when Robert had the opportunity to stay over. One night, a line was crossed when the boys were masturbating as Jeremy reached over and placed his hand on Robert's hard penis. Shortly after, he grasped Robert's hand and put it on his own penis. The whole scene was taboo, and Robert knew it was wrong, but he had never felt anything as exciting in his young life. Touching another boy's penis as the other boy grasped his own lit a fire of sexual burning he never knew could exist.

When Jeremy got up and took off all his clothes Robert followed suit without hesitation. Both boys stood naked in front of each other pulling on each other's penises. Jeremy tenderly began caressing Robert's hairless naked chest with his free hand. Robert did the same to Jeremy as this touching of each other's naked flesh led to a passionate embrace with the boys soon softly kissing each other. In this explosion of sexual discovery, the two naked boys climbed into bed together and their romancing continued unabated.

Kissing, hugging, nuzzling, pulling on the other's penis, rolling around in each other's arm the boys experienced all the tenderness of sexual embrace that they had yet to know in their lives. When Jeremy placed his mouth over Robert's penis and began sucking it, Robert had never felt anything so wonderful.... till he returned the favor and began sucking Jeremy's cock. The taste and sensation of sucking Jeremy's penis gave his own hard penis a wonderful ache. The boy's took turns sucking each other's cocks till finally each boy took turns masturbating the other to ejaculation. These climaxes were wonderful and there was no awkwardness this time, only a loving connection. As they nuzzled and kissed each other, not able to sleep, Jeremy kept whispering "it's our secret, okay?"

The boys slept little that night. The warmth and excitement of being naked with each other led to periods of deep slumber and then wakefulness with the erotic fondling of the other boy's penis. Each boy masturbated the other to ejaculation in the middle of the night. In early morning light, Robert's mouth found Jeremy's penis and the boys took turns sucking each other's cocks before masturbating cummies onto to each other's naked flesh. Then, finally, with Robert slipping into the sleeping bag beside the bed as was the usual custom of the boys spending the night at each other's house, slumber took hold and they dozed into sleep till the sounds in the household woke them. No one knew what a life-changing night had transpired between Jeremy and Robert. For Robert, as he walked home and then interacted with his mother and sister, he felt out of sorts, guilty, ashamed, unsure of what to think about what he did with Jeremy. When he saw Jeremy in school, they were friends still, but now friends with a secret.

Robert also had another secret. Living in a house with two attractive females and with his mother out of the house much of the time and his sister working part time after school at Mr. Taylor's store, Robert had ample time alone in the house. It was only natural that with women in the house and no male role model, curiosity would creep in about all the wondrous articles of female clothing that were about. Panties, bras, leggings, dresses, slips, camisoles, bikini swimsuits, shorts, tops, a myriad feminine milieu constantly surrounded the boy.

About the time when Robert and Jeremy began their mutual masturbations was when he had tried on a pair of his sister's silky bikini panties. The sensation and arousal he felt wearing them made his stiff penis ache and the ejaculations that occurred while masturbating in them were mind bending. The guilt and shame he felt wearing panties and trying on bras, swimsuits and dresses was immense. But the guilt and shame was not nearly as strong as the immense pleasure he felt wearing and masturbating in his sister's and mother's clothing. The dynamic in his relationship with Jeremy was changing too. Even in his goth persona Jeremy was somewhat more masculine than Robert and was more assertive and persuasive.

After school, with Robert's mother and sister at work, sometimes Jeremy would come over. In the past they might play video games or shoot hoops, now the boys had but one thing on their minds; their developing sexual sensations. One afternoon Jeremy was sitting on the couch at Robert's house and the sexual tension was quite high as they were alone together. Robert excused himself for a moment. When he returned, he had on a pair of his sister's simple cotton bikini panties and one of her bras. The panties had tiny little flowers on them and a pink bow and a matching bra with its own little pink bow in the center.

Jeremy smirked a little but said nothing as Robert sat next to him and began pawing at Jeremy's penis through his pants. Robert climbed onto Jeremy, and they began kissing in the passion of this new twist Robert had brought about. It was stultifying-ly erotic and Jeremy caressed and fondled Robert's penis through the panties. Robert felt possessed with lust and an incredible sensation of femininity washed over him as he threw himself on to the other boy. Jeremy pulled off his shirt as Robert opened Jeremy's pants and pulled them down about his ankles, revealing Jeremy's erect penis. Kneeling on the floor in front of the couch, Robert played with Jeremy's penis before engulfing it in his mouth.

Robert had sucked on Jeremy's cock before, as had Jeremy on Robert's. Jeremy's cock was substantially larger than Robert's with a nice mushroom head. Jeremy certainly did not mind Robert sucking on it and the pleasure and desire of a big penis being in his mouth gave Robert sensations bordering on obsessive.

"Such a pretty little cocksucker," Jeremy cooed as Robert sucked his cock.

Robert's own penis twitched and ached hard as he heard Jeremy say these words. He pulled on his penis, tenting in his sister's soft panties as he continued sucking the other boy's penis. The whole sensation of being in panties and a bra made Robert's femininity soar and sucking on a boy's cock felt like the most wonderful, most natural thing in the world to do.