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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, Part 2: The continuing story of a young married man who discovers sex with another man. After losing his anal virginity the previous night, the young man decides he wants to please and fully receive his friend Glen and discovers new ways to pleasure himself while he explores his own body. His young hormones rage higher once he finds his prep for Glen alights new pleasures he’s never dreamed of, not to mention increasing his sex life with his wife. The goal wasn’t to please his wife through secret solo anal masturbation, but to eventually feel Glen inside him with the maximum amount of comfort and pleasure.
Personal note: This is the continuing true story of my budding sexual relationship with Glen and picks up where the first story left off. It’s about my self-exploration of anal masturbation, but there’s a scene of sex with my wife. Sorry, I still put it under the Gay Male category since that’s the direction the story is going. There is also some trial and error, which I’m hoping is not unique to me. This is a bridge to Part 3 which is more self-exploration via a new dildo! I will get back to Glen and me in part 4. Also, the activities, objects, and feelings are true, but not the names and exact places.
Previously from Part 1 …
I got home about the usual time as if I had gone to a party and went to the bathroom to get ready for bed. My increasingly hard dick wouldn’t go down and had sprouted full again. So, I jacked off with one hand and circled my ass hole, that was hot and had self-lubricated, with my fingers while replaying the night I just had. I came into the sink within a minute! As I orgasmed, I felt these wonderful contractions of my asshole on my finger and wanted Glen’s dick back there. I think I was hooked. It was the first time in my adult life I came twice in an hour and realized that with a little bit of Glen’s cum still in me that my ass had also self-lubricated! I cleaned up and waited a few minutes before I could crawl into bed without a hard on.
I snuggled up to my wife, who was in a deep sleep, and drifted off to sleep with thoughts about what Glen and I could do next and a flood of guilt for waiting until after I was married to sexually explore.
Part 2
After waking up early next to a still sleeping Susie, I was surprised to find my morning wood still greeted me. My morning erections were never associated with horniness, but this one was. Apparently, the hours-long, intensely aroused state I was in the previous night, not to mention cumming twice, caused a new stimulating morning surprise. I started smiling as head-swirling thoughts of my first anal sex the previous night flowed through my head and veins.
Beyond the erection, my backside was a little sore yet slightly pleasurable as I felt my heartbeat tingle my ass hole. I lay in bed a few more minutes thinking when I could again be with Glen. With some effort, I ignored my morning wood by getting out of bed and starting my day.
After Susie and I had breakfast and chatted about our nights, we got our day started with errands and chores. Of course, I left out of the conversation what really happened the previous night and replaced it with what became the usual lie, going to the after-bar party, chatting with people, and sometimes going out for a late breakfast. I felt bad about what I did but also chalked it up to just random exploration that would go eventually go away. I thought I could resist it happening again but knew I didn’t want to resist just yet.
In the late afternoon when I took my afternoon bathroom (“library”) break, I had an itch just inside my anus that seemed to tickle at the same time as I had my BM. I started to think about the sex I had with Glen and whether I damaged something or caught an STD. Little did I know at that time it would have been too early to have STD symptoms the day after, but such was my worry and ignorance. (And, lucky me, I never caught istanbul travesti an STD). I had also asked Glen before our consummation if he was clean, and he said he was and didn’t just screw around with random guys. Regardless of my concerns, there I was sitting on the toilet, hard as a rock.
I ignored my aroused state, finished, and got on with the day. My dick stayed chubby as my wife and I finished the laundry in the bedroom. But, out of a now-urgent need, I started flirting with her and she was equally reciprocating. This led to making out and somehow making our way to the walk-in closet.
We went down to the floor, partially over our shoes, as my wife took hold of my cock and I mashed my hand over her puffy pussy lips. She pumped me a few more times before I asked if she was ready. She said, “Oh yeah!” I quickly stripped off her shorts and licked and kissed her soft, milky thighs while she got my shorts down just enough to spring my cock free. I went back up to her face and we kissed deeply and sloppily as my fingers parted her slick lips and I quickly entered her with one thrust. With great, unbridled sex amongst our shoes, we laughed about how uncomfortable we were and how it didn’t matter. Susie had sparse, soft pubic hair that didn’t cover her inner lips, so the thrusting was smooth and sexy. I should have admired her pussy much more and took for granted how great it was. My thrusting was much longer than other times in bed and she was loving it, and so was I! I needed more access and lifted one of her legs over my shoulder to go deeper, which started my orgasm. At the same time, I felt her pussy tense up indicating her orgasm was on the way, so I tried to hold off a few more seconds by pulling out almost all the way. Suddenly, I felt the first jolt and rammed back in as my breathing halted. Susie’s pussy started to vibrate around me and my cum finally exploded into her. Her orgasm started full on as I felt her pussy tighten while a flood of juice surrounded my engulfed cock as I pumped more cum into her than I thought possible.
“Oh, Christ! Where’d that come from?” Susie breathed out.
“Just thought we’d do something different other than at night and in bed. Was it good?”
“Yeah, but I think the shoes got dripped on,” as she rolled away laughing.
The rest of the night was typical, but flirtier before we settled into bed. I wasn’t one for daytime sex, but Susie enjoyed my newfound interest to fool around in the middle of the day. I felt a bit superhuman with three massive orgasms in 24 hours, but I was spent. Still, I couldn’t get the night with Glen out of my head the rest of the night, and really the rest of the week.
About midweek my libido recovered, and I planned some time for myself at home between classes. Susie worked full time during the day so I knew I’d have blocks of time for some self-exploration. This time I got the dumb idea to make my fingers slipperier with a sandwich bag and some Vaseline. Even though I already knew what worked for me – spit and objects, or Vaseline and fingers – I thought I could make entrances to my anus better with plastic. This was not a great idea and made me bleed a bit with the bunched-up plastic being forced into me. However, it allowed me to explore a different way with two of my fingers without too much mess. (I don’t recommend this method!) After a few uncomfortable minutes, and because I seemed to be forcing myself to play, I gave up for the week.
The weekend finally came and went without much happening at the bar. My wife had come with me both nights since we felt “closer,” but that didn’t stop Glen and I from sneaking touches when we could. Him and I didn’t talk about the previous weekend, but we knew it was our secret. The work nights were filled with suggestive talk, teasing, and flirting with me from both Glen and my wife, each without knowing the other side of the situation. Susie and I had sex after one of my work nights and it was great, but normal.
That whole weekend I felt odd about how I loved my wife and yet still could have a connection with Glen. I sort of figured that I could explain it away if Susie ever found out. And how could she ever find out when it was happening in front of istanbul travestileri her? It was only later in my marriage that the remorse and disrespect hit me hard. I feel bad for her to this day.
I returned to doing more self-exploration during the next week as I was determined to give more of myself to Glen and wanted more of what he had to give. My stashed condom, from my single days, was in my older wallet and the idea hit me to use it instead of plastic bags or unwrapped fingers and vegetables.
I got home from school, dropped my backpack, and checked that Susie wasn’t around. I grabbed two carrots, instead of one I knew I could insert, from the fridge and went into the bathroom. I got the condom and my heart started to race as I stripped off my clothes. I unwrapped the condom over the two carrots and lubed them with some spit. I sat down in my usual position for anal play by leaning against the outside of the tub and used more spit to lube my hole. My 21-year-old dick anticipated the fun by becoming mostly hard. I lined up the carrots to my hole and started to push them in. They hurt a little since they were pointy, and I wasn’t used to two of them going in. They went in only an inch since due to my tightness. I pulled them out and removed one carrot from the condom and added more saliva my hole and began to push the carrot back in. Whoa! The single carrot almost slid in too easily with the condom. I wondered why I didn’t think of this before! The carrot felt so good as I kept pushing it, and it felt as if it was partially being sucked in after the first couple inches! I felt the usual stopping point about 5″ inside, and as I started pulling out, I felt a whole new sensation as the unevenness of the carrot glided across my sensitive rectum.
Adding more spit, the carrot-carrying condom went more smoothly in, and I started to stroke it in and out of my hole feeling every nub and curve of the intruding vegetable. I loved watching it disappear into me and got used to the feeling. Hell, I was loving the feeling and wanted more!
I felt my anus finally relax, removed the carrot and was able to get my middle finger in with no problem. I also noticed that my ass was way slicker than the saliva I added. I knew I got a bit slick with previous anal play, but now it seemed to be producing its own lube at a faster rate and much more than ever. This encouraged me further as my hole seemed more accommodating than any other time, so I was able to insert my first finger alongside my middle one! It was tight and I couldn’t get more than a couple inches inside before the stretching became uncomfortable. I was excited because there was no actual pain.
(Side note: my anal lube production made me think, stupidly at the time, whether I had some internal parts like a woman’s natural lube mechanism. I knew a couple years later (with regular internet access) it was natural for your colon to produce some “lube” to pass stool, especially when you’re younger. Eventually my ass started to anticipate something being in my lower colon, including increased sweating outside my hole, and in just a few months I actually didn’t need a lot of lube for a couple years. I’ll save that for a future story.)
After a couple minutes of my fingers pumping and probing, I put the carrot back in. My cock, completely forgotten at this point, was going through agony so I started jacking it as I stroke my phallic veg in and out at a medium pace. A thought hit me – I wanted the carrot thicker since I wanted to accommodate Glen, so I picked up the second carrot and slipped it into the condom with the other carrot still in me. The other carrot had to come out a bit more to be as thick as my two fingers. I felt the second carrot going in easily until the stretching became taut. I started pushing them in and out slowly, going about 3″ deep. Another revelation occurred when I took a big breath that dilated my anus, I could push the carrots in further! Holy shit, they went in to 5 inches easily but then my ass clamped down tight. At once I felt the carrot tips poking me inside and my hole starting to hurt from clamping down. But the excitement and feel of 1.5 inches of thickness inside me allowed my anus to finally open travesti istanbul up more comfortably.
My cock got super hard, and I started jacking it furiously while pumping the carrots in my ass. I started a throaty whisper, “Oh, oh, Glen. Fuck me Glen, fuck me. Uggghhhhhh.” It took only a few seconds before my orgasm started, and it started without cum shooting out. What the heck?! My dick looked like it tried cumming on its first three twitches, but then I felt my cum rise up the length of my penis to shoot out forcefully two times onto my sparsely hairy chest. Then my cum flowed at a lava pace at each orgasmic pulse of my cock the rest of the time. I didn’t know what to think but figured this odd cum event must’ve been due to my anus not being able to close. My orgasms back then were very dick oriented, I only felt them in my dick and not in my whole groin and lower abs area as I do now.
Once I regained my breath, I pulled the carrots out and felt a small amount of liquid come out of my ass with them. I checked it for blood and there was none. Phew! My hole immediately closed shut, but then opened and closed like it was begging for more. With cum drying on my chest and matted in my pubic hair, I cleaned up and thought of the new milestone I reached.
As I retired to the couch to do some homework, my dick was still inflated. My studies were disrupted by thoughts of why my dick was still semi-hard: was my body just reacting to pent up horniness that still wanted more, or was I thinking about Glen and what my new milestone would mean to taking him into me?
Getting distracted reading my homework, I had to change positions on the couch and put one leg under me. This had an odd effect of pushing on my sensitive hole and really got me thinking about what I just did and how good it felt. I seemed to develop a new sensitivity inside as I felt the entirety of the carrots and where they had prodded for the first time. I felt a new, and better, feeling at my entrance I hadn’t felt before. I enjoyed the thought of the new amount of natural lube I produced. It was then I got up to shut the curtains so others couldn’t see me and returned to the couch. I quickly shoved my hand down the front of my pants to my hole and, surprised by the heat and sweatiness, I started to rub my bud in circles.
I had never fingered myself this way before, so I laid back on the couch to enjoy it. I undid my pants for easier access, pushed my hand down further and easily inserted my middle finger in my ass when my knees instinctually raised. Wow, I was still wet inside and a little came out when I started flicking and pumping my finger. The sloppy squishing sound was just like fingering my wife but doing it to myself was very arousing. My dick rose to full staff quickly, and I had to get myself off. I jumped off the couch and ran to the bathroom.
There I was, back in the bathroom where I was just a few minutes before and stroked myself to another orgasm right over the toilet. The stroking lasted longer and the amount of cum was smaller, but it was like I hadn’t fully satisfied my sexual hunger from before. Maybe my dick needed to be inserted into something before the horniness went away? After that second orgasm, I was spent and had to nap. So much for homework! Luckily, being young this sort of “double-orgasm” within an hour by jacking off was something I could do, but not too often.
The rest of the week was uneventful since I couldn’t play with myself again. I was a bit ashamed, sore, and somewhat disinterested. My work weekend came up and Susie didn’t come along, but Glen and I flirted and teased as usual. At the end of Saturday night, he asked about sticking around and I said sure. We went to his place, but I told him I played with myself too hard “back there” during the week and didn’t want to do anything. He said kind of jokingly and laughing, “Why’d you do that?”
I responded slightly embarrassed, “Well… I want to be ready for you. Can you give me some time?” I was surprised by my answer since I wanted Glen right then and there, but I felt this self-consciousness about being perfectly ready for him to enter me without issue.
“Sure. But don’t think I don’t care about you. I can take it easy with you. Just tell me when you’re ready.” Still the newbie, I didn’t think about blow jobs or other fun, and I’m not sure Glen did either. We hung out and drank a bit more, grabbed and groped a bit and I went home with very blue balls.
To be continued …
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