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Jerry opened the door to see Sam standing there wearing a huge smile that quickly changed to a look of surprise and fascination. Stunned into silence, the man came in as Jerry moved back inviting him forward. Jerry closed the door behind the man and welcomed him to his home. “Sam, I was expecting a delivery man; I’m very happy to see you. Come in, make yourself comfortable.”
Sam hadn’t said a word yet, his mind was processing what he was seeing. Jerry was standing there wearing a skirt and top, and he had breasts, and hair. Sam knew Jerry was a crossdresser from conversations with both Jerry and Kay, Jerry’s wife. What he hadn’t expected was for Jerry to answer the door, dressed in women’s clothes. He couldn’t help it his eyes scanned the womanly dressed man before him and took it all in. Jerry was wearing a pair of pantyhose, his skirt, a light colored flowery, material that seemed to flow as he moved, came down just above his knees. His top, a soft light pink sweater, was just snug enough to highlight the fact that Jerry had breasts. And the hair; Jerry was bald, but now sported a long red mane of hair. It took a moment, maybe too long of a moment, but Sam regained his composure and thought, this is not a bad thing. He remembered why he had come over in the first place, and his smile returned.
“I was driving by the neighborhood, I saw your car and thought I’d drop by and say hello.” Sam was excited. Jerry welcomed him into the house. “I just put a fresh pot of coffee on, should be ready in a few minutes,” offered the host. The pair sat on the sofa until the coffee was ready.
Jerry was no fool. Sam lived at least an hour and a half’s drive away, on a good day. Jerry knew that Sam didn’t know anyone else in this town, he said so himself when they moved here. Sam had never, to Jerry’s knowledge, even been to this town before, and now, suddenly, he’s ‘in the neighborhood’. Jerry knew what was on Sam’s mind, but he played it cool, letting the man make the first move.
“Where’s Kay?” Casually asking about Jerry’s wife, Sam was obviously anxious.
“She’s working today”, answered Jerry.
“On a Saturday?”
“Yea, her shifts are so sporadic. She left this morning at 5, and likely won’t be back until 5 or 6 tonight. We never really know when her shift will end, it depends on the number of people that show up, and the actual work they need to do.”
Remembering the coffee, Jerry stood up and went to the kitchen. Sam was intrigued by the skirt and how if flowed as the man walked into the kitchen. Sam followed shortly after and arrived as Jerry was pouring the coffee.
Sam fixed his coffee; there was an uncertainty in his expression, he was anxious, and Jerry knew he was struggling with what he wanted to say. Jerry leaned against the counter sipping his coffee as Sam fought the internal struggle of whether or not to admit why he was really there.
After a pause, Sam took a sip, mustered his courage, and said, “Look, I was hoping … maybe, we … you, could do that thing again”. Jerry found the hesitation in his voice cute. He certainly was having a hard time trying to come out and say what really brought him to the house. Jerry, as much as he wanted to tease the man and ask, ‘what thing?’, he decided the man had nervously suffered enough. It was time to take over the conversation. Setting his cup on the counter, Jerry moved close to the man laying his hands on Sam’s chest.
Slowly, Jerry let one hand drift down over Sam’s abs and rested on the waistband of his jeans. With a slight twist of his wrist, his fingers were under the waistband and drifting slowly into Sam’s pants. Soon, Jerry, still quietly smiling at Sam, held the man’s hard cock through his boxers.
“Would you like me to give you a blow job, Sam. It seems you could use some assistance here.” At that he gave the man’s cock a gentle squeeze.
Sam smiled broadly, nodding, “yes”. His soft and low voice still betrayed his nervous state. The man’s mind wandered back to the first time Jerry had sucked his cock. It was spur of the moment and as much as he enjoyed it, he was fairly certain they wouldn’t get caught. Today, however, was a different . Jerry had commented that Kay could be home anytime.
Insightful, and realizing what Sam was thinking, Jerry said, “Remember I told you that Kay and I are very open and honest with each other?”, Sam nodded, “Well, on the drive home that night, I told her all about me sucking you off. She was very intrigued and asked a lot of questions. She’s going to be over the moon when I tell her you dropped by today for another one.”
Sam’s face lit up with relief, his body relaxed. Jerry squeezed the hard member once more and began to slowly massage it through the material. Sam turned to put his cup down on the counter, as he turned back, Jerry’s free hand moved from the man’s chest up to his face. Cupping his cheek, bringing their faces closer together, Jerry asked, “is that all you want Sam?” The man’s eyes betrayed him, Jerry knew there was something else and he made his move to prove it. With a slight turn of his head, Jerry placed his lips over Sam’s and kissed him.
It was only a moment before Jerry felt Sam kissing him back. It was tentative, and brief, but it was there; Jerry felt it, a passion, buried and suppressed. Sam pulled his head back, but stayed close, Jerry’s hand still massaging his cock. Sam’s mind racing with conflicting feelings.
Sam had several girlfriends over the years, and even a few after he married Betty over 26 years ago. He didn’t run around on her a lot, but he enjoyed some spice in his life, and over the past few years especially, he and Betty had settled into a routine. It is why he had been looking for someone else to play with just a month ago. That tryst fell through, partly because of him, and partly because of the other woman. It was in the telling of that to Jerry one evening soon after that saw Jerry kneeling and sucking his cock. His mind raced that night too, but it was different then, he needed relief, and Jerry provided it without cost or need for reciprocation. But, that night in bed, next to his wife, he fell asleep wondering what it would be like.
Sam’s face was inches from Jerry’s smiling bright eyes, his cock being held by him, softly squeezed, and gently massaged. He loved the man’s touch, and he had to admit to himself that he liked the kiss. He struggled with the fact that he didn’t ‘like’ men.
Glancing up, he saw the wig Jerry was wearing, the soft red hair looked real, and like it belonged right there. He recalled the clothes Jerry was wearing, the detail still fresh in his mind. Jerry was presenting himself as a woman, and one that Sam knew he had begun to want. Would he really be kissing another man, or the woman he saw before him. His justification was tenuous, but enough for him to move in and accept another kiss.
This time, the kiss lasted longer. Sam enjoyed it even more than the first. Still his mind played back his fears. When the kiss broke, he felt a small bit of relief, and a large measure of regret. Before he could move back in for another kiss, Jerry was sliding down to his knees. Sam realized that Jerry was no longer holding his cock but was now opening his jeans and sliding them down his legs. He let the host undress him. Very soon, he was naked from the waist down except for his socks. His cock being held again in the gentle grip of Jerry’s hand as it slid along the shaft.
Jerry kissed the tip of Sam’s cock, licking the precum that had accumulated there. He moaned as he savored the taste. His mouth opened and engulfed the other man’s cock, taking it in slowly, letting his tongue lick the underside as it passed. It was Sam’s turn to moan.
He began a slow motion of his mouth along Sam’s hard member, softly sucking as he moved, tickling the underside of the man’s cock with his tongue. Sam’s moans became louder and more frequent. It didn’t take long before Sam’s cock swelled in Jerry’s mouth and began to spurt his load. Jerry swallowed the first spurt, and then let the rest pool in his mouth until the man was spent. Sucking to clean his shaft as he pulled away, Jerry let the semierect cock slip from his lips without losing any of the accumulated cum.
Sam looked down at the smiling face of Jerry staring back at him. Jerry’s mouth opened to show Sam the cum. Sam smiled as he watched Jerry swallow the rest of the cum.
Standing again, the pair were close once more. Jerry’s one hand cradling the softening cock, while the other caressed Sam’s cheek. Jerry waited.
Sam wanted another kiss, he knew it and he also knew that he may very well taste his own cum on Jerry’s lips. The struggle inside of him was real, and at any moment he wasn’t sure which side was winning. All the while, Jerry stood there holding and caressing him, smiling, waiting patiently for him to decide. Sam felt no pressure to do anything other than the pressure he was putting on himself. He knew he could pull back just as easily as move into a kiss, and was confident that Jerry would not care which choice he made. He felt the man’s empathy for his predicament, and began to feel something more, something he hadn’t felt in a long while. A desire.
It was like a wiper blade sliding across the windshield, the worry, the doubt, the anxiety, the fear, the trepidation, all wiped away in an instant, replaced by the clarity of desire.
Sam moved slowly, but deliberately towards Jerry, seeing the man’s smile grow every brighter. Their lips met and a warmth ran through Sam as he gave himself over to the passion he was receiving from Jerry. Their kiss was long and slow and filled with meaning. Sam’s thoughts had become a jumble trying to interpret the feelings he had at that moment, but he let himself get absorbed by them rather than trying to figure them out. It was a while before he recognized that Jerry’s arms were around his neck, holding him into the kiss, the man’s hand caressing his hair. What surprised Sam the most though was his own hands were around Jerry’s back, holding him close just as much as he was being held, if not more. Their heads turned together, the shape of the kiss changing, but their lips never parting. Their tongues tasting and teasing each other.
When their kiss finally broke, Sam gasped, catching his breath, then said, “That was fantastic. I’ve never …” then his demeanor changed, and he tried to pull back from Jerry’s loosened embrace.
“Shhh…It’s alright.” Jerry said, holding the man softly, but prepared to let him go. He spoke softly, calmly, as a mother calming a crying child. Sam felt the positive and supportive energy in his words and stayed tucked into the shared embrace.
“It’s a difficult thing to figure out sometimes, the desire takes over, but the mind has to rationalize all the feelings and the conflicts. It’s going to be alright Sam, you’re still you. Kissing a man, letting a man suck your cock, even doing more than that doesn’t change who you are, it only releases more of who you are.”
Jerry bent over and gathered Sam’s clothes. Taking his hand, they went back to the living room and sat next to each other on the sofa. Jerry put his arm around Sam and cuddled his head into his shoulder. He continued, “We grew up in an age where we weren’t allowed to be ourselves, forced to suppress the feelings that were considered unnatural. That was wrong. We needed to have those feelings so that we could understand them and how they mattered to us. I thought I was happy for years, married to my first wife, having children, and just living. I always felt something was missing. When she passed, I began to explore things, and realized I was biual, and more so, that I loved the way I felt wearing women’s clothes. Sure, I borrowed my mother’s panties when I was a young, but the need to be normal kept me from enjoying and pursuing it any further. I felt a new freedom until I met my second wife. She was too set in her ways that I needed to present as normal. She knew I liked to cross dress, but it still had to be a secret that I couldn’t even share with my grown children. When she and I divorced I met Kay, and never again felt I needed to hide anything. Now all our children are grown, and they all know about my biuality and my cross dressing. They have even seen me dressed, and what is more important is that they all support and love me.”
After a pause, “I know it will be hard for Betty and your children to understand you this way, but take comfort in knowing that Kay and I do, and if this is the only place you can fully express yourself, then so be it, we will be your outlet, you need an outlet.”
Sam sobbed softly into Jerry’s shoulder.
A few minutes later, Sam spoke, “I admit, I’ve been conditioned to think being with another was wrong. But I’ve always had a curiosity, one that I would never allow myself to explore. When you sucked me off that night, I felt something that I hadn’t felt before, and it brought back that curiosity. That was part of the reason I came here today. Certainly, I wanted another blow job, but secretly, I wanted to see how it would make me feel otherwise.”
“So, you weren’t just passing by?” Jerry quipped. He laughed.
“Saw through that did you?” he said, sitting back up. “I’m happy I did though.”
“Are you on a time schedule or can we talk some more, maybe actually drink our coffee?” Jerry asked laughingly.
“I’d like that.” He looked down to see his naked legs and exposed cock. Following his gaze, Jerry saw that his cock had begun to harden again. Without comment, he leaned over and took the hardening member back into his mouth, bringing him back to full strength and continued to suck and tease.
Sam’s hand drifted to Jerry’s crotch. Tentatively sliding over the bulge. Jerry shifted himself so that Sam could get a better feel without releasing the man’s cock from his mouth. Sam spoke, “I’d like to see it.” The words were soft and almost hidden in his breath, but Jerry heard them and slowly released the man’s cock and sat up.
Without a word, he stood and slid the skirt down and off, tossing it over the chair where Sam’s jeans were laid. Sam stared at the pantyhose covered bulge, the sheer tan material did little to hide the pink thong that Jerry was wearing underneath. Jerry reached his hand into the pantyhose and without removing them, slid his cock free from the panty material. All that stood in the way was the sheer pantyhose. Sam had seen other men’s cocks before, he was big into sports at an early age and shared many a locker room. This was different though, this was a cock he wanted to see, and he admired how it was presented for him encased in the tight hose. Jerry stood still as Sam reached out and glided a finger along the shaft. Soon he was rubbing it through the pantyhose.
“If you want, I can lay down and you can get a better feel.” He did that without waiting for an answer, Sam moving off the sofa and kneeling on his thighs on the floor next to him. His hand back on Jerry’s cock, sliding, squeeing, rubbing, the firm member.
Sam stopped his movements, and looked up at Jerry’s face, “I don’t think I can …” he trailed off.
“You don’t have to suck it if you’re not ready, just play with it like you’re doing now, have fun with it. If you continue what you’re doing, I’ll cum in my pantyhose.” Jerry paused, “Or do you want me to take it out for you?” Sam gripped the cock and was able to stretch the material so he could get his fingers around the shaft. He began to masturbate Jerry in earnest. Soon Jerry’s head went back, and he began to moan. Sam knew it wouldn’t be long and continued to manipulate the member, rubbing and softly twisting his hand as he did. The material of the pantyhose made it so much easier, he didn’t require any lubrication. Soon Jerry’s breathing changed and he moaned louder. Sam felt the pulsations and continued to stroke the cock as the cum spewed through the mesh material and onto his hand.
He kept going until Jerry had stopped spurting cum. Sam lifted his hand and looked at the cum that was coating it. He had never tasted cum, not even his own, and he wasn’t sure if he wanted to then either. Jerry sat up, took Sam’s hand and licked the cum from it. Sam stared in amazement.
When Jerry took Sam into another kiss, Sam was surprised that he liked the taste of Jerry’s cum. They kissed sharing it between them.
Minutes later, the pair were sitting back on the sofa, both of them naked from the waist down, Jerry having removed the cumstained pantyhose and thong. They drank their coffee and talked about things other than what they just shared. Old friends, catching up as if nothing had happened.
For the first time since he could remember, Sam was actually comfortable talking to another man about something other than sports.
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