Budding Sexuality with Glen

Disclaimer:

This story is a work of fiction. I, as the author, do not condone any act or activity in the story. All characters in this story are 18+ years old. Any resemblance to any persons, living or dead, and any resemblance of places current or past, are purely coincidental.

Inside Jacket Synopsis: It's a mostly true story about the budding sexuality of a young man who just graduated high school and discovers porn mags and new ways of self-pleasure. He meets Glen and they build a friendship over time. But, this man's desire for a perfect life with a new girlfriend, later his wife, will not stand in the way of his sexual exploration. Is he becoming attracted to Glen, or the attention his friend gives him? Does he pursue a physical situation? It's responsible not to explore while he's engaged and then married, but wanting something his body succumbs to is different.

Personal note: My first story. The backstory is a bit long, but is key to the feeling that builds to the climax in the latter half of the story. If you want the "good" stuff, go about halfway down. I'm open to feedback.

I cringe when I read all the "first time" stories glorifying how easy, non-painful, and fun anal sex was when it finally happened. Sure, I wished my partner had a plan, or there was a bed, or there was lube available. However, none of those occurred and my first time with a man was just forbidden, naughty fun with a little pain and a lot of nervousness. It is not the sexiest, most arousing romantic story, but I can't wait to tell you about my first time with a man. In a nutshell, it happened in a restaurant/bar after it closed for the night. The activities are true, the rest is not. Let's start at the beginning...

The late 90s, 18, and freshly graduated from high school. I was too immature for college, but all my friends weren't and they all planned to leave for school in the fall. My parents, completely unhelpful to get me to college, provided me a cheap place to live. Those first few months after high school I made habits of working, getting high and drunk, and buying porn magazines. (Penthouse Letters was my go-to). I had a carefree life with the occasional girl coming along as a friend-with-benefits to satiate my teenage hormones.

As expected, the entirety of my friends left town for college in the fall, and I continued to work at Green's Cafe, a greasy-spoon restaurant open from 6:00am to 3:30am. Working the late-night shift was great since I could run the place like my own, but also gave me the freedom to get high with the cooks a couple nights a week. The restaurant was surrounded by a few bars within a half mile which created a bar rush crowd until 3:00am with drunk, hungry and horny people hoping for a last-minute hookup with other drunk patrons. As it would happen, I started to get after-bar regulars certain nights of the week.

Weeknights was when I noticed a regular group of guys showing up a couple times after bars closed. They were always drunk and would sometimes flirt with me, which tipped me off they were gay. I wasn't gay, nor attracted to any of them, but liked the flirting regardless of gender. I considered the flirting part of the job. I didn't know of a gay bar in the area but, I thought it was cool they could feel comfortable going wherever they wanted (it was the late 90s and Iowa wasn't all gay-friendly at the time in our college town).

One of the guys from the group, Glen, seemed nicer to me than the others. Apparently, they came in during the week since Glen worked weekends at a restaurant and bar that was farther away. Many nights, after the majority of the bar-rush crowd left and his friends took off, Glen would stick around to chat with me until I closed the restaurant for the night.

I never knew Glen's real age but guessed he was in his early 20's and was about 5 feet 10 inches with a slightly soft body - not overweight, but proportional. He was one of those lucky guys who never had to shave, and seemed smooth on all the exposed areas I could see. He had a slightly darker skin tone, which I found out later came from his mixed Asian/Euro ancestry. While I didn't find Glen attractive, that would change as I got to know him more.

At 18, I was naive and certainly didn't know a lot about sex and relationships. Through Penthouse Letters I learned about threesomes and butt play and even tried some things with my summertime girlfriend. Of course, there were no letters ever published with man-on-man activities, and I never really thought I'd want to 'go there' with guy anyway. On the other hand, and maybe out of boredom from masturbating, I started exploring my own personal butt play that summer after high school. I had starting putting things in me like carrots, handles, and my fingers, while I got myself off. (Fun story for another time!) I seemed to be looking for a feeling, but couldn't find it. I just knew that it made my orgasms a bit more intense and liked the feeling.

Winter descended upon Iowa and the restaurant business slowed down. But parties still went on around the town until the wee hours, and it was one of those parties that I met my new girlfriend, Susie, who'd become my future wife. She was smart, stable, with a seemingly perfect life and we hit it off right away. She inspired me to go to the local college and I soon attended as a full-time student while working the restaurant. Since all my free time was with her there was no longer time for partying or exploring. Though I did occasionally explore myself when I was alone.

While Susie and I dated, I would talk incessantly about her to Glen. I even talked to him about proposing to her. He was obviously annoyed because he and his friends stopped coming in after the bars closed. When they did show up, they kept me at a distance. Though after some time had passed, we became friendly again.

About 18 months later, a few months before I got married, Glen suggested I work at the restaurant/bar he worked at during the weekend. It wasn't a gay bar, just a local restaurant that was a bar at night. He said it was more money than what I was making, free drinks and food most of the time, and that he had put a good word in for me with the manager. It sounded great!

I met the manager the next weekend and he gave me the job on the spot. The job was only on weekends, which solved my school schedule issues, and I found that I could make more money in one weekend than working six days at the restaurant. The job was a dream since my fiancée could party a bit when I worked and partake in the free food and drinks.

Glen became a really good friend of mine after I started, and when I had a free night from homework, I'd head to the bar to hang out. I also noticed he didn't really attempt a friendship with my fiancée. To his credit, after the first few weeks on the job he developed a habit of putting more tip money in my pockets at the end of the night because, he'd say, "You earned it."

I was married a few months later and we decided to wait on a honeymoon. So, I was right back at work the next weekend and Glen was the same person as the week before and also really happy for me. But, as the weeks went on, he started getting very touchy with me, especially as my wife wasn't showing up much anymore. I still ignored Glen's flirtations as I did when he'd come into the previous job I worked at. However, the more I accepted the flirting, the more drinks and extra cash came my way.

Glen's flirting began to include some 'accidental' touching and became more frequent. He started putting his hands into my pockets with extra tip money and would look directly into my eyes and say it was for doing a great job. One time this happened, his hand lingered a bit longer and I realized there was a stirring in my crotch - I liked his hand in my pocket! To not overplay my semi-aroused state, I told him, "Stop it, someone might see." I wasn't being serious; I was just playing along. He then kept his gaze on me, smiled, and slowly pulled his hand from my pocket with a short tug of it.

I still didn't think of him as sexy, and I was married anyway (!), but I started to be flirtier just to feel his hand on me. His touch made me confused whether I really liked it, or if I just liked the forbidden touch from someone that wasn't my wife. My hormones ran wild over my responsible adult thinking. Wasn't I supposed to be responsible because I got married? From that one moment of Glen's pocket tug, I started liking his attention in a real way and not for free drinks and money.

Susie stopped coming to the bar as she had enough of the same old weekends, so I started going to the after-bar parties instead of going home. The parties were mostly regulars from the bar, and it's where I could hang with Glen a little longer.

At the parties, I mostly talked with Glen and flirted a few times, and he continued real touches of me. At times we'd get too noticeable and people would joke about Glen liking me. I liked the attention, but felt the jokes were too dangerous and I returned to being "straight and married" the rest of the night. I didn't act gay and everyone knew I was married, so everything seemed okay.

The touching by Glen during work became more frequent. He knew I'd become comfortable with it when no one was around. I loved it when he'd brush my ass with his hand, or touch my arm to tell me something. I also got used to touching him with fake shoves, back tickles, hip checking him (causing him to express some sexual double entendre like, "It must be getting slippery in here because you keep bumping into me.") I loved the secret flirting and I started to wonder where this might go, and do I want to go there?

Over the next couple weekends, I got bolder near the end of the night as the drinks loosened me up. I would fully grab his butt or his inner thigh, in private of course. I loved the feeling that I was turning him on and started to see Glen sprouting a bit in the pants. Glen started getting bolder as well, doing similar things and matching my touches. I moved on to the occasional light crotch squeeze when I saw him getting a little excited, which he'd respond softly, "What are you doing?" I'd usually smile and walk away to work again.

One time after my first crotch grab of the night while we were in a darker section of the bar cleaning tables I said, "Let me make sure you don't like it" and of course found he was semi-hard. My first actual grab of another man's cock, although through his jeans, immediately made me hard! This surprised the hell out of me and made my hormones spike. Playing it cool I said, "Oh, so you do like that?"

With a touch of sexiness in his voice, "Well, what do you expect? You get me hard more often than you think." Glen stepped toward me with sort of a side nudge as he grabbed back and said, "Let's see if you like it. You do!" I immediately left the area smiling at him, and adjusting my crotch, with an extra sway of my hips and a super horniness I will never forget. I had to jack off in the bathroom stall a few minutes later to stop my raging hard on. I pulled my pants down, sat on the toilet and stroked no more than 10 times before I shot so hard that I completely missed the tissue I held in front to catch my cum. My cock didn't go down right away, but eventually went down to a semi hard for the rest of the night. In my haste and horny state, I forgot to wipe off the cum from the stall door. Glen cleaned the bathroom that night and pulled me in to show me "something." I'm not sure he saw the embarrassed look on my face when he showed me the dripping cum and said, "Apparently someone was horny enough tonight! This is the first time I've seen this." I'm not sure Glen suspected me, but he certainly wanted to react which I did with a 'wow' and a 'that's interesting' and then left right away. Yep, he probably thought it was me.

The whole next week I kept thinking about him and how we could continue the fun. This kept me horny the entire week, and even two extra nights of sex with my wife didn't help! I didn't know what I should do with Glen, but decided I'd go all-in with him and figure it out when it happens.

My next weekends at the bar now had me semi-hard all night due to the anticipation, along with a needed jackoff session in the stall. Glen's and my secret grabs started to be longer with a quick rub when it came to the front of our pants. I began slipping my hand from his thigh up his crack knowing I'd get the same treatment back at some point. I loved that whatever I did, Glen would do back to me.

One of the next weekends the nights seemed typical, but with a few more tequila shots floating around. Close to bar closing Glen and many regulars planned to go to an after-bar party. Like other nights, the manager asked Glen to clean and close the bar. I told Glen I'd stay behind to help with the light cleaning. Glen didn't make the connection that we'd be alone, or he ignored it on purpose. As we rushed to get done I'd steal a few touches and grabs since no one was around, but he wasn't reciprocating. Weird, I thought, and just kept going.

When we finished cleaning we were in the maintenance room. Glen was washing his hands and I was behind him so I grabbed his ass saying, "Ooo, look at this!" being playful and very drunk. I felt bold and was semi-hard of course so I pushed my crotch against his backside for the first time. Even after jacking off nightly in the stall the past few weeks I still had tons of spare hormones.

Glen laughed a little and said playfully, "What are you doing? You want to get to the party don't you?"

I said, "Sure. Is that what you want to do?" The game was now on...

Glen, with a quiet voice asked, "Did you want to do something else?"

After he finished washing his hands I scooted past him to wash mine. "I don't know," I shrugged. "Maybe."

Glen was now behind me and started moving his hands on my ass and towards the front. Glen went into his sexy voice, "Well, what does that mean?"

I got so hard I was going to bust out of my jeans. My voice cracked a bit high, "Let me wash up and then decide."

As I did so, Glen reached around and massaged my cock through my jeans like he's never done before. He stepped forward and I felt his covered cock against my ass. I instinctively started moving my ass around on him as it felt great. "Well, we can stay here," Glen said. His earlier aloofness of was gone.

I finished drying my hands and turned to face him not knowing what to do. He wrapped his arms around my sides to rub and caress my back, butt and thighs and brought our jean-covered bulges as close together as our 3" height difference allowed. He was breathing heavily and kissing my neck (he was as tall as my nose). He tried to suck and bite my neck but I broke away for a moment and said, "No kissing and no marks." I didn't want my wife to notice my passionate indiscretion. As his hands kept exploring me, I momentarily became catatonic and just stood there with my arms at my sides feeling all at once excitement, curiosity, arousal, embarrassment, sadness, and nervousness.

I started shaking uncontrollably and Glen asked soothingly, "Are you okay?"

I swallowed with a dry mouth and said, "Yeah. Just... nervous... and cold. But I feel good and you do too." And with those words I wrapped my shaky arms around him to do what he was doing to me. Nibbling and kissing his neck seemed to arouse me even more and helped me calm down. My body responded instinctively by wrapping one leg around his ass and legs while I leaned against the sink.

I let my leg go from around Glen and backed myself up to the chest freezer. Glen followed, reached under my shirt and started to rub my slightly downy chest. He then went down to the waistband of my jeans. I undid the top button of my jeans and his hand as far down as he could get it. He barely touched my cock, and it brought about a gasp from me. I quickly undid the rest of my jeans and let them fall to my ankles. Glen said, "Mmm, that's better," and brought my cock out through the fly in my boxers to gently stoke it. "You're big!" I could hear the smile in his voice.

I said, "Thanks, but I think I'm average." I'm not large, I'm actually 6.5" and a bit narrow, but liked his compliment. I realized I was only massaging Glen's ass, so I started massaging his cock through his jeans. That was another huge turn for me. By what I could feel, Glen's penis was smaller than mine. Glen stopped softly kissing my neck and I kissed his for a moment before he looked down and bent over to take me into his mouth. Another "wow" left my throat along with consistent moans. I instinctively started slow thrusts at his mouth and he could only fit about 4 inches of me. Watching his head bob up and down and feeling his warm, soft mouth on my hard and ready-to-cum cock was so hot I forced him to stop because I wanted more of him in a different way. Back then I wasn't into getting blowjobs, and I'm still not (except one time, but that's another future story). The sexiness and newness of what we were doing was very stimulating so I removed his face from my dick before I came. I said to myself, I want his dick in me.

As Glen came back up I undid his jeans as fast as I could and reached inside his boxers. My first skin to skin touch of cock! It was hot, smooth and super hard and Glen had a compact light bush of hair above it. I noticed my hand almost covered his whole cock (he was about 5.25 inches). I had no judgment about his size, just that it was hot and sexy. I didn't feel like giving him a blowjob at the time, but wanting more, I asked, "What now?"

Glen commanded softly, "Here," and guided me to sit on the freezer with my pants still around my ankles. Glen moved forward and pulled the front of my boxers down and went right back to sucking my cock while my splayed legs were still connected to my jeans at my ankles. Not getting enough access, he pulled my boxers down to my ankles and came back to sucking my cock and began massaging my balls, something my wife didn't do. He licked my cock up and down a couple times before moving to my balls, licking them all around before nudging them with his nose to lick underneath. I started jerking myself out of necessity and realized if I didn't stop I was going to cum. And then, the night of surprises continued...

Glen flicked, licked, and sucked lower and lower until his tongue touched my asshole. A strong involuntary shiver went through me and I gasped as my hole instinctively constricted. My mind was blown with all kinds of thoughts, but I couldn't resist the feeling of his tongue licking and caressing my hole and throated loudly, "OH, GOD, OH GOD!" I tried to thrust my ass to meet his tongue like my wife would do when I licked her pussy, but my position didn't allow that movement. I even laughed a bit at my embarrassment and the feelings I was having while my legs were spread in mid-air. I thought it couldn't get any better, but then he hardened his tongue and poked it into my very tight hole as far as it would go. He wiggled it around just inside me with his face against the insides of my cheeks. His mouth and tongue were magic on my hole by sucking, twirling, poking and thrusting. It felt so good as he slathered my opening bud with his saliva that I grabbed his head to keep his tongue in me and brought my legs in to surround the sides of his head. I was so confused about loving it as I felt at once how a woman may feel, but also manly because he found an erogenous zone that maybe only a man knew what to do with it. I got into a nice moaning rhythm with a higher pitch I never knew existed from me.

With my hands on his head while he ate me out my mind finally focused on the new feelings. I relaxed once again and Glen must have sensed it and immediately took charge. When he came up, he said, "You taste good" in his sexy, giggling voice. He pulled off my shoes, took my jeans and boxers off, and shoved his boxers down to his thighs. He got in between my legs and tried to connect his cock to my hole. I was breathing heavily and felt the need to spread my cheeks while I stared at what was about to happen. I wanted to see his cock go in me. I was up too high for his cock so I scooted my ass to the edge to angle my hole closer to him, and he was able to connect his cock to my hole. I thought, "Just put it in!" as my arms reached around to force him in. I didn't want to be a virgin and I wanted him to fuck me. The moment of truth came as he pushed forward, but I was way too tight and dry. Even though he had eaten me out for a few minutes I was too dry and tense.