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, Part 4: The story of a young married man who discovers sex with another man. After losing his anal virginity in Part 1 and discovering new feelings while preparing himself to take Glen more comfortably in Parts 2 and 3, the young man is now ready to give himself to Glen.
Personal note: It’s a longer read, but hopefully worth it! This is last in this series about my true story of my budding sexual relationship with Glen. After this, there will be more stories on exploring and fun with Glen, in chronological order. Also, the activities, objects, and feelings are true, but not the names, times, and exact places.
This stands on its own pretty well, but if you want the story of how it all got here, please read parts 1 – 3.
I was ready for Glen. It had been a couple weeks of my own solo anal play and a few nights of sex with my wife. At 21, I was continually horny so every day seemed filled with some type of sex.
In the weeks since I lost my anal virginity to Glen, and got a dildo, I learned my ass and my brain needed to be on the same page to enjoy newfound arousal. I discovered two fingers wiggling, thumping, and caressing my inner walls was almost better than jacking off, but also didn’t lead to orgasm. I also found the fullness of riding and grinding on my dildo while masturbating brought about a new level of orgasm I wanted more often.
Then, there were times I might rush insertions which caused a little blood and pain. I also discovered there were times I shouldn’t play due to, well … waste in my lower colon. I wasn’t familiar with enemas at the time but would later learn about them. Generally, my ass play over those weeks became a normal part of my solo sexual routine.
Before continuing with the sexy parts of my story, my relationship with my wife was great; she was none the wiser about my anal play. I know I was disrespectful with my thoughts and actions from my secret life but felt I could do no wrong at the time.
The weekend was finally upon me where I planned, but didn’t exactly plan, to have anal sex with Glen. After a few days off from solo playing, I felt horny as hell and badly wanted Glen in all sorts of ways.
Friday at the bar was typical between Glen and I, grabbing and teasing the entire night. I planned for Saturday night to get him alone as I could have the usual excuse for coming home late from an after-bar party. I hinted to Glen about Saturday that there might be a surprise for him. He kept asking, “Really? What is it?” while poking me in the ribs. I told him to be ready for whatever it is.
We did our usual clean up after the bar closed on Friday but I made sure to flirt with him more than usual. As we left, I made sure to push my pants down enough to show him a little of my ass. Glen laughed, “Nice ass! You’re trouble. Do I have to wait for my surprise?” I gave a “Mm, hmm,” pulled my pants back up and drove home thinking about Saturday night.
Saturday went by in a haze of chores and errands. By the time I was on my way to the bar I couldn’t wait to be with Glen. The anticipation also gave me higher expectations than I should have.
The entire night, Glen was asking, “What’s my surprise?” or “Are you sure I’m getting my surprise tonight?” I kept responding, “You’ll know,” and “What do you think” with teasing touches.
Closing time came and I asked Glen, “Are you still going to the after-bar party?”
“Yeah, aren’t you? You owe me a surprise!”
“Sure. But can we make our own party? You got beer at your place?” It was ballsy of me to invite myself to his place, but I knew we needed to be alone.
Glen grinning said, “I may have some, but only if you tell me why we need to go to my place. Carl may be there.” Carl lived with Glen, but I never thought much of it as they were never a “couple.” Nor did I care they lived together. They always told people they were brothers, but weren’t, and I always thought Carl was straight. He was one of Glen’s friends that hung out at the bar almost every night Glen was there, and he was part of the group that would come to Green’s Café, my former workplace. He was quiet and tended to stay in the background, so that’s why I haven’t mentioned him until now.
“If Carl is going to be there, maybe we’ll wait,” not fully aware of Carl’s attitude towards me, or me with Glen for that matter.
Glen quickly lowered his voice to be more enticing, “He already left for the party. He won’t bother us if we’re there…”
“Well, okay. Fine,” I said jokingly. We closed the bar, and we went to his place.
I gave myself a tour of Glen’s home. It was small, comfortable, and a bit run down, but it was on its own private land. Glen’s bedroom was the master as it had a bathroom in it and was on one side of the home, ankara travesti Carl’s was on the other side with the living room and kitchen in the middle. Glen broke out a beer for each of us and we chatted while playing darts for shots.
Glen seemed to be losing on purpose, and after two games, three shots and a few beers, we started groping each other more than playing darts. A grind here, a grab there, and finally a few reaches inside pants to check if the other person was ready for the “surprise.” After a short pause in darts, Glen needed a bathroom break and I told him I had to get something out of the car. It was the KY.
I came back in and started towards his bedroom and bumped into Glen in the dark hallway as he came out of the main bathroom. “Where are you going?” he asked.
“I was going to check out your bedroom. I didn’t get a good look at it before.” I made my way to the bedroom and flopped on his unmade bed. It smelled of Glen, a bit like cologne, and a bit natural like my own scent. I sighed and pretended, “I’m tired. I suppose you forgot about your surprise. We should sleep.”
Glen scooted up onto the bed next to me with his head propped up on his hand looking at me. “Well, if you don’t want to surprise me, I can surprise you.” As he said it, his hand started to softly palm the front of my pants where my cock was growing intense. I returned the petting to his full staff and closed my eyes while I mewed to signal my approval of his touch.
Our petting got bolder as he reached under my balls to caress near my hole. I grabbed his butt and pull him closer to me. I leaned back to lay on my back and freed up my right arm so both hands could knead his ass. Glen, partially on my upper body, began nuzzling my neck with soft kisses while his hand made its way under my jeans. I was already slightly sweaty from the earlier arousal which helped Glen’s fingers slide easily back and forth between my balls and bud. I never really thought of being fingered before, but it was heaven.
In a somewhat uncomfortable position, my cock jumped at his bare-handed grab of my dick. I gasp, “Ohhh… ahh.. Glen … ” My groin instinctively thrust into the air at the feeling of his warm hand taking hold of me. His other hand undid my jeans and he let go of my member to push my jeans and boxers down enough to release my balls. I was rock hard when Glen started pumping my dick with a sensual slow rhythm.
My hands worked under his shirt rubbing and massaging his back while he began pushing up my shirt. As he pushed my shirt up to my neck Glen kissed up my arm making his way to my chest. He began kissing and tongue-flicking my chest and down to my belly. I started to shake and get cold again like the first time we were together a few weeks before.
“Maybe I should warm up,” I told Glen through heavy breaths. “I don’t know why I get this way. I want you so badly.”
“I’ll take care of you. You don’t need to surprise me. You already do. Let me put a blanket over us.” Glen grabbed an extra blanket nearby to throw over us and we adjusted to a more normal, yet cozy, position on the bed. He put my shirt back down and rested his head on my chest. I tilted my head towards his and could smell the lingering bar, restaurant, and hint of his shampoo. I also smelled something familiar, a scent like my own, manly without being musky or funky. I was comforted by it, but in a different way than my wife’s hair, which always had only a fruity scent.
As we lay there, my right arm wrapped around his back while he rested his right hand on my lower belly, just above my now flaccid penis. “Wow, I can hear your heart beating fast. Just don’t worry. You don’t need to rush.” I smiled and gave a little grunted smirk staring at the ceiling, wondering a thousand things: should I leave; this seems all wrong or all right; I should go for it and ignore my betraying physical feelings.
I calmed down after a few minutes and was warm again. I asked, with a gentle grab of his butt cheek, “Are you still awake?”
“Of course. It seems you calmed down a bit,” Glen looked up at me with half-closed eyes.
“I think I’m warmed up now and ready to give you your surprise.” I leaned over so we were facing each other on our sides. I leaned in and started kissing and sucking on his neck. Glen moaned an erotic sigh, and my left hand went right underneath his pants to grab his dick. He quickly rose to my touching, and he undid his pants for better access.
With the blanket still over us, Glen took the initiative and lifted my shirt and started kissing and licking my chest. Then down to my belly. His right hand found my now half-hard cock and started to palm it gently while his fingers tickled and rolled my balls. Glen’s mouth and tongue were starting to drive me wild. Both my hands started to run through his hair like a relaxing massage. I resisted pushing him towards my cock as I wanted to enjoy every moment of foreplay.
He loosely encircled the base of my cock with his hand and made small rotating and stroking motions I never thought to do. ankara travestileri He alternated with reaching his fingers out to roll my balls, and every few moments he’d reach a finger down to caress my bud. His kisses were getting lower, below my belly button, over to my hips and down to my pubic hair. I felt the warmth under the blanket and Glen’s breathing became heavy with arousal.
I flopped my left arm over my head, while my right found its way to Glen’s shoulders. I surrendered myself and let him enjoy me as he wanted.
I was experiencing another man’s touch and felt a rush of arousal wash over me. Glen planted kisses around the base of my cock, on my balls and even took one into his mouth to softly roll it on his tongue. He was teasing me as much as he could. I felt his head raise and a lift of my penis and then … his hot mouth enclosed on just the tip of my head with a wet kiss and a sweep of his tongue across the head. My dick twitched hard, and my pelvis thrust upward at this new erotic feeling, but he released quickly. I gasped, “Oh, God,” needing more of those feelings. He gave a couple light strokes of my cock and pushed the blanket off us.
“Are you okay?” Glen whispered.
“Oh yeah! Keep going.” Glen moaned and laughed his signature “mm, hm,” and then went down encircling my cock with one downward thrust of his head. He got most in as he started a nice slow rhythmic up and down on the shaft while his hand cupped and fondled my balls. His focus on my shaft and not the head was the difference between what he knew to do and what Susie didn’t understand about blow jobs.
My hands went back to caressing his head while I looked down to see my cock disappearing into his mouth. It hit me suddenly, this blowjob by a man was far better than any woman that gave me one. Although Glen had briefly blown me the first time we were together I was too focused on adjusting my position and getting him in me. This time it was sensual, sexy, and in full-realization I wanted him in every way. I giggled from joy from my new internal eroticism.
I was writhing and started thrusting my cock to meet Glen’s willing mouth. But, after just a couple minutes it was enough. I wasn’t big on getting blowjobs, so it became a bit boring as the initial feelings dropped off. Hell, if I didn’t want him in other ways, I would have let him finish me if he wanted to. When I stopped him, he said, “You can cum you know, you don’t have to worry about it.”
“But I want to do other stuff. Maybe I’ll try you,” I got up to move Glen around onto his back. I pulled his pants and bright blue briefs down to his thighs, exposing his cock. Wow, I was up close and personal with his dick, never seeing any man’s dick this close before. His 5.5 inches was hard, hovering over his belly and pointing towards his head. I knelt beside him and started stroking his smooth member, instantly feeling the heat of his cock in my palm. While I knew the feeling of a cock in my hand, I felt the difference in sexiness with someone else cock in my hand and the position of it.
I admired his compact bush, his hairless belly and chest, and the smoothness of his legs while stroking him. My free hand started gliding across his thighs and balls and sometimes underneath. I mimicked what he had done to me by kissing his belly and chest, down to his thighs and just above his pubic hair. His male scent wasn’t off-putting, nor erotic, but it was like I was smelling something that, again, was familiar. I was at ease with it. A woman’s scent, like my wife’s, was so foreign and different to my own that it was mostly something I just accepted as different; although there were times I really liked it too!
My hand job was a bit rough, and I felt bad when Glen started to go a bit soft. I should have realized that Glen might not like the way I masturbate, as I was applying my own technique to him. I noted it for future times since I got self-conscious and wanted to move on to getting his cock in my mouth. It was a goal, but also a deflection to get him excited again after my poor first-time hand job.
I never sucked a dick in my life and didn’t even think about how it might be. I didn’t think about taste or feel of his cum, or what I would do when he did cum. I just wanted him in my mouth. I never felt this way, just succumbing to my feelings for the pleasure of another. I never thought, “I want that woman’s vagina in my mouth,” but if the time was right I would do it too.
Grabbing the base of his penis, I glided my mouth all the way down his cock. I loved it! The feeling of his warm, smooth flesh in the moist confines of my mouth and on my tongue made my own cock tighten. The way the head and glans of his circumcised cock going across the insides of my lips and the tickle of his pubic hair on my nose was nothing I thought could feel so sexy and arousing. How could I get more turned on? But then, the learning curve happened.
“Careful of your teeth,” Glen whispered through a soft voice. Knowing it was my first time giving a blowjob, it was sloppy, and I felt bad travesti ankara if I had hurt him. I apologized and went slower with more mouth flesh to his cock.
I wanted to make him cum, to taste him. Since I had no practice, I just thought going up and down on a cock would feel great. After a few minutes I was getting tired and felt that Glen was getting bored. So, I forced myself down the entire length of his cock to spice it up, but it made me gag a little. Glen wasn’t going to cum in my mouth this time, or any time for that matter. My poor blowjob skills were causing Glen to lose interest, again. I felt like a terrible partner.
Now that I think about it, Glen never produced pre-cum, or maybe he did, and I ignored it. I only mention it since a few years later I realized how hot and sexy tasting my own pre-cum is and missed out on Glen’s.
I gave up on the blowjob as Glen was losing interest. I started taking off my pants and boxer shorts completely — leaving my shirt on. I reached back to finger myself a bit and went back to kissing Glen’s belly and chest. I stroked him back to full hardness as I moved my body into a 69 position with him. He took me into his mouth while I only stroked and kissed his cock and pubic area. After some time, with both of us at full hardness, I said, “Time for your surprise.”
“Oh really. What’s that?” Glen sexily asked as he grabbed my butt cheeks and pulled my cock into his mouth as deep as it would go.
“Ahh, Let me show you.” With that I got up, grabbed the KY from my jeans, and knelt on the bed near Glen’s lower legs. I squeeze KY onto my fingers and spread it on my hole pushing and twisting a finger inside to get me lubricated. I noticed I was tight but made sure to pull open my hole a bit to stretch it. I scooted up to straddle Glen’s thighs and started to lightly caress his cock. I said, “Your surprise is that you’re going to get me pregnant!” My voice had gone up an octave.
“And how am I going to do that?” Glen was playfully full of questions. “Are you sure you can handle it?”
“Well, let’s see if this fits,” I said as I wiggled his penis. “But first, let’s get these off.” I shimmied back down his legs and pulled his pants and briefs completely off. I went back up to straddle his cock and reaching behind me I grabbed hold of it and said, “I want you inside me. I want to make you feel good.” I placed his cock at my entrance and felt the head slightly push against my tightened hole.
“You already make me feel good.” As he finished talking, I started lowering myself onto Glen’s dick. I felt the slickness of the KY while his cockhead entered me. But there was too much pressure. I raised up to grab him and wiggled his head across my bud a few times feeling all the tingles and nerves in the area, and wedged it back in. The stretching was a bit more bearable with some slight pain. I was rushing and didn’t care — I wanted to feel him inside me as quickly as possible. Lowering an inch to get through the stretch I started to push out to open my entrance more, but there wasn’t a lot of movement. I then started to piston on Glen’s dick with the inch I was able to take. The feeling was sensational with his cock head popping in and out. Glen was trying to relax me by stroking his fingertips on my thighs.
I released Glen and felt stickiness coming on from the drying lube. I put more KY on my hole and this time put some on Glen’s dick. I said, “Maybe this will help,” as I began stroking his cock with slippery delight. Glen started to moan which was my cue to guide his cock back into me. His very lubed cock went in easily past the first ring. I moaned a bit and started moving up and down slowly, knowing I could go further. I wanted to fully sit down on him except I felt constricted by my inner ring. Slowly I moved in a rocking horse way listening to the sucking sounds of my canal on his cock. I looked down to see my cock pointing straight out, harder than ever, bobbing and pulsing with my movements.
I felt Glen’s cock squeeze past my inner ring. There was progress and the pain started to subside! With determination and a small groan, I slowly lowered and engulfed Glen’s cock all the way in. I felt his pubic hair tickle my balls. I gave a short ecstatic laugh as my dream of taking him in a sensual way was fulfilled, I stopped to enjoy the feeling. “How is that?” I asked as I started to make small gyrations with my ass.
“You feel good. How are you?” Glen was the every-so-caring guy. I wanted to do anything that would make him want me.
“You feel really good. I’ve wanted you inside me for so long,” as I said with increased breathing. I felt my insides wanting to push out the invader, but all that did was open my hole to accommodate Glen better. I started grinding on Glen a bit faster. Glen responded with pelvic thrusts helping me forget about the little hurt that was left. I lifted and hovered over him so he could thrust into me. I was feeling an increasing need for Glen to cum in me. I wanted his seed and wanted Glen to really start fucking me, but I had trouble finding the sensual feelings I had at home. I felt warm and full with Glen in me, but I think my forced insertion turned my wonderful feelings into something non-descript. I figured it was me trying too hard. I no longer cared, I wanted Glen to do whatever he wanted with me.