The original post: /r/eroticliterature by /u/SleeplessNights711 on 2024-09-20 02:18:10.
Dave was never a dominate man, standing at 5’9 around 158 lbs with most of the weight naturally going to his thighs. His wife would often joke about how it wasn’t fair that he had a better ass than her. Of course, she was blessed more than most when it came to her breasts. It had been five years since his beloved wife had passed away and he was just now getting to a place where he could see himself going out but he had decided long ago that his wife would be the last female he would ever love. He had gone on dates with other women since but they had all been a disaster. Everything they did reminded him of her. The way they brushed their air back, the way they dressed, one girl even wore the same perfume as his wife. It had all felt like he was trying to replace her with a different version, it had just felt wrong. So after a long internal struggle he had decided to explore the side of him that he had been suppressing since he was 15 and showered with the other boys after gym. He had decided to date men.
He made a profile on multiple different apps two days ago but was too worried to even look at them. “What are you doing?” Kept running through his mind. The thought “Your a 36 year old man who has only dated his high school sweetheart. Do you really think anyone would be into you?” Was a close second. He was in his office at work when he finally decided to check the apps, unable to resist any longer. His jaw dropped when he saw how many messages he had received. Apparently, the picture of him lying on his stomach in a speedo that he had taken a few years back was very popular. He did have to admit it showed off his ass and legs in a great way. He was so absorbed in replying to messages he jumped at the sound of a knock on his door.
“Working late tonight Dave?” A female coworker named Ashley said. “You alright you look a little flustered?”
Composing himself he replied “no I’m fine. I just lost track of time playing this new game on my phone.” That was a stupid lie he never played games.
The suspicion was written on Ashley’s face but luckily for him she didn’t press the matter “Well you better get out of here while you can. See you on monday.” She said over her shoulder as walked away.
Dave gave it about ten minutes before leaving the office and heading home. While driving he couldn’t help but check his replies when traffick came to crawl. He had been messaging with a few people but only one really stood out to him. OldFashion75 had been smooth talking him all day and Dave had to admit his heart speed up when reading his replies. A quick search of OldFashions profile showed he was a 49 year old 6’3 225lbs white male with short hair and a beard that was graying but still had splashes of brown in it. Where Dave seemed to carrying most of his weight around his hips/thighs OldFashion seemed to carry most of his weight in his chest and arms. From the pictures on his profile, he looked to be more muscular at 49 than Dave had been his whole life. Once he got home he rushed upstairs to take a shower, while in the shower he could hear his phone going off alerting him that there were men trying to flirt with him.
While airdrying he scrolled through the messages before finding OldFashions reply. He had sent the location of a local gay bar and asked to meet for drinks tonight. Dave’s heart was about to beat out his chest. “Are you really going to do this?” He thought “Oh calm down it’s just a conversation…with a guy you find extremely hot.” He didn’t even notice that he was fully erect at the thought of OldFashions pictures. He took a deep breath and replied. “Looks like I’m close wait for traffic to die down and meet you there say 8ish?”
He hadn’t even gotten to his dresser before he heard the phone go off. He rushed to the phone reading the reply “it’s a date.” He let out a squeal of joy. Dave spent the next hour frantically
trying on outfits. He had no idea what to wear on a date with a man. Did he dress up, dress down, did wear something that showed off his legs, did he dress more feminine, or would that turn him off. He eventually settled on a pair of black leggings and a white crop top that would only expose a slight mid-drift. He posed infront of the mirror looking at his ass wondering if this was too girly but ultimately decided he wanted to show off his best asset on the first date. He put on some deodorant and looked at himself one last time in the mirror. He examined his face making sure his facial hair wasn’t giving a 5 o’clock shadow but like normal it was pretty much non-existent. Dave put on a slight layer of lip gloss before grabbing his keys and heading out the door.
As Dave pulled into the parking lot he could tell there was a modest amount of people already in the bar. He sat in his car for 5 minutes working up the courage to go inside when his phone went off. “I got a table in the back. See you soon.” Attached was a picture of him at a table with a drink in his hand. Dave looked at the clock right at 8. He took a deep breath and went inside. As he walked in he could tell everyone was staring at him. The bar crowd were older men appearing to be from late 40’s all the way into 60’s with a few men in their 20’s scattered around. The attire seemed to be predominantly t-shirt and jeans. Dave had never wore his leggings outside his garage gym and the thought of these men staring at his ass while he walked by both excited him and made him nervous. He was about to leave when he saw Mr.OldFashion in the back waving at him with a smile. His smile was so warm and inviting that Dave completely forgot about all the eyes on him and walked to meet his date. He was wearing a button down shirt tucked into a pair of form fitting jeans with cowboy boots.
He stood up “Littlespoon08?” He asked. Dave nodded with a smile. “I’m OldFashion75 but you can call me Richard.” He said extending his hand. Dave took his hand and without thinking replied “I’ve never met a Dick i didnt like.” He dropped his head, his cheeks turning three shades redder. “I mean its nice to meet you I’m Dave.” Trying to recover. Richard couldn’t hold back his laugh " well please have a seat and lets see if I can keep your dick streak going." Dave buried his face in his hands. “Your off to a good start.” Dave said laughing. “First things first can I get you a drink?” He said pointing to the bar. Dave nodded still hiding in his right hand. “What would you like?”
“Oh um well let’s see…I like old fashions.” Dave said dropping his hand to reveal his red face.
“A man after my own heart. I’ll be right back.”
Dave looked over his shoulder watching him walk to the bar. He enjoyed the view of Richard’s butt in the jeans as he walked away. “Looks like I have some competition.” He thought playfully to himself. Richard returned holding two old fashions sitting down across from Dave. Over the next few hours and many drinks they went from sitting across from each other to next to each other with Richards hand caressing Dave’s right thigh. Dave could feel Richards hand brush against his penis a few times as he gently rubbed his thigh. This only caused it to grow in length which then led to his hand bumping into it more often, which then caused it to grow. It was a vicious circle but not one he wanted to end anytime soon. Richard wasn’t just a kind, smart man he had a sense of humor too. He had caused Dave to snort at least twice, which had of course sent him back to hiding behind his hands. “Your cute when your blushing.” Richard said before leaning in to whisper in Dave’s right ear. “I can think of a few other ways to make you blush.” He then kissed Dave on the base of the neck sending tingles all through his neck and down to his groin. Dave unconsciously tilted his head exposing his neck to Richard’s lips which were now working their way up to just below his ear lobe. Suddenly he felt Richards hand slide up his thigh cupping his now completely erect penis. Using his hand he massaged Dave’s penis as he kissed his neck forcing a moan to escape his lips. “You like that.” Richard whispered more of a statement than a question. All Dave could do was nod as he bit his lower lip trying not to bring attention to them but he could feel the pleasure building in him threatening to erupt from his mouth. Richard pulled away.
“So you really have never done anything with a man?”
“I went down on Billy Sparks in the 10th grade but after that I met my wife and never did anything else.” Dave explained. “But the urge was always there. In the back of my brain.”
“Did you ever kiss Billy?”
“What no way we werent gay or anything.” They both broke out laughing.
“My mistake.” Richard said after collecting himself. “And now? Would you like to know what its like to kiss a man?” Dave nodded again too nervous to summon the words. In one motion richard pulled Daves chair around to face him pulling it in close. You could see the surprise on Dave’s face. He was not use to being on dates with people that could man handle him like that. He had to admit though it was a huge turn on. Richard leaned in placing his hand on the back of Dave’s neck pulling him slowly to his lips, his thumb gently stroking Dave’s cheek as he stopped centimeters from him. Dave knew he was teasing him, bringing him so close and then stopping hovering at his lips. He couldnt take it anymore and leaned in pressing himself to Richards lips. The combination of his beard hair on Daves chi…
Content cut off. Read original on https://old.reddit.com/r/eroticliterature/comments/1fl1j96/first_date_m38_m49_masturbationkissingfantasy/