Budding Sexuality with Glen Pt. 03

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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 3: The continuing story of a young married man who discovers sex with another man. After losing his anal virginity (in Part 1), the young man explores his new feelings from his own anal exploration, finally purchasing a dildo to use as the best way he can prep for Glen. His new toy seems to be the ticket for receiving Glen in comfort and pleasure, but he doesn’t realize the internal sensuous heights he would experience on his journey to making Glen and himself happy and satisfied.

Personal note: This is the continuing true story of my budding sexual relationship with Glen and picks up where Part 2 left off. It’s more self-exploration, anal masturbation, and understanding my interior body. As with many great discoveries in life, there’s a happy accident, or two, that sets the stage for my future use of dildos, good and bad (in a lessons learned sort of way). This is a bridge to Part 4 where Glen and I get physical again. Also, the activities, objects, and feelings are true, but not the names and exact places.

Previously from Part 2 …

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.

Part 3

The next couple weeks were the same, sex with Susie and self-play during the week, and teasing and touching with Glen at the bar and after-bar parties on the weekends. My own ass play during the weekdays started getting easier and became part of my regular masturbation sessions. I was now able to easily insert one finger and then a few minutes later insert another. My natural lube only took some mindful anticipation to get it going, but a little saliva and the feeling of something in my lower canal really got it to flow.

Another week went by before I was able to insert a third finger for the first time by breaking out my stashed KY I bought grocery shopping. The attempt with a third finger was not great and caused little blood from stretching my entrance, so I cut the session short. I tried three fingers again later that week, and it went much better with no blood and better feelings. This second time got me a little wider, but not a lot of depth.

That Saturday, after my shift at the bar, I told Glen I was tired and was going straight home. I was anal sexed out for the week and did not feel ready for him. As I headed home, I got the bold idea to stop at the adult toy store. I had extra time not going to an after-bar party, so Susie wouldn’t know.

I shyly, but also determinedly, perused the dildos and sized up what I should get. I also noticed a few older guys that seemed to be wandering and looking at nothing specific in the store. They would walk by me slowly, and I didn’t realize at the time they were trying to pick me up in some way. I had no interest in them. (That would change another time in the store.) A few more minutes there and all the sex stuff was arousing me. I wanted to go back to Glen as my cock started up and I felt my inner cheeks start to get wet with excitement.

In order to not show the small tent in my jeans, I quickly decided to buy a 7-inch dildo that was 1.25 inches wide at the head, with no balls or suction cup — my first dildo! I thought it looked like a good size, and definitely bigger than me, but it seemed to be the most popular size they had; what did I know about dildo size and my backdoor? I went to pay and made stupid small talk to the clerk, like I was buying a gag gift for a bachelorette party or something. I’m sure he didn’t care, and I istanbul travesti was just talking out of nervousness. I hid the dildo in a bag in my car trunk’s wheel well, went home, and waited to try it out during the next week.

Mid-week arrived, and I was on my way home from a break in my class schedule when my thoughts of using the dildo caused my ass to heat up. It was time to try the dildo! By the time I got home I was sporting a chubby and got fully hard getting the items from the trunk. I got into the apartment, grabbed the KY I had stashed, some paper towels, and almost ran to the bathroom to unwrap my new toy. It smelled weird so I washed it off and started to jack it like my own cock. This jacking had an unexpected effect on me, making me want to jack off Glen. But it was the pre-cum making my boxers damp that brought me back to what I wanted to do with that robust rubber penis.

I put down a layer of paper towels on the floor next to the tub, undressed completely, and sat down on the towels with my back against the tub. Not thinking of prepping my hole, I put some KY on the dildo, which looked huge, and lined it up to my hole. I hurriedly tried to push it in, but it wasn’t going. Then I tried wiggling it, which felt great on the outside, and still no luck with some stretching and throbbing pain appearing; not unbearable though. God, I wanted it badly and didn’t have the patience, but had to succumb to what my body was telling me. I set the dildo aside and lubed my fingers.

First finger went in with no problem due to the KY and my now flowing ass lube. I only went in about an inch and I noticed I was tighter than the previous week. After a few minutes of relaxed fingering, I snuck a second finger in with relative ease, but with a bit of anal ring tautness. A few more minutes of flicking my two fingers back and forth, my hole relaxed enough for me to try a third finger. This was a bit tight as well but after a minute I was so worked up that my natural lube was causing some squishing sounds and making it much easier for my three fingers to pump away in and out of my hole. I also didn’t feel the stretching of my first anal ring, and the internal ring was also giving way. I sat up on my three fingers and felt past the internal ring and that really got me going! I started to rock back and forth on my fingers while my dick bounced helplessly in time. Holy shit, what a feeling I had going. I had to try the dildo again!

I again lubed up the dildo with lots of KY and scooped some of my leaked ass lube to slater it on my rubber friend and my hole. I leaned back against the tub and lined up the dildo with my hole and the head slipped in, with little pressure, stretching my outer ring. This caused my inside ring to constrict, and I stayed this way trying to breathe through the stretch. This was the largest, most solid thing I had inserted but somehow knew I could take more if I relaxed.

“This position may not be working,” I thought and got the idea to squat over it. I rose on my knees, my rock-hard dick pointing straight up against my belly, and lowered myself to hover over the dildo. I lined it up and steadied it with one hand while I lowered myself to the point where I felt it at my hole. I used my hand to wiggle it back and forth over my hole sending new feelings radiating from my back entrance to my insides. The dildo just didn’t want to go in. I tried to try to wedge it in which helped, and it slipped about a half inch beyond the entrance. After a couple more gyrations of my hips, the head slipped in, and I felt a comfortable tightness. I stayed in that position for a minute or so and started to relax and feel the new hugging of this solid object. I started to breath more slowly and the rubber cock seemed to start getting sucked into me! But this also hurt, and I had the urge to push out the invader. As I pushed out and the dildo started to come out, I shifted and missed sitting on my heels evenly.

HOLY SHIT – I basically sat down on my haunches and I felt the cock thump pass my internal ring as it slid in about 3 inches. Instantly it felt great, and I laughed with pleasure as it slid in, but I stopped the next half-second when my anus constricted and there was a throbbing pain. I stopped and tried to bear through it and did so for a few seconds before I started to rise off it. Raising off the dildo didn’t feel as good, but my ass wanted it out quickly! As it exited and fell bouncing onto the floor, my violated hole started constricting and opening on its own. If I pushed out it felt better, but when I let it constrict, it throbbed in a bit of pain.

I started to massage my hole with my fingers adding KY to the mix of my anal lube to pet myself and rub my sore hole. This felt good even istanbul travestileri though my hole was on fire. I still wanted the fake dick in me and was so focused on jamming it in that my dick had gone limp and shrunk to its “cold” position. The massaging of my hole made it feel better and I checked for blood and there was none. Whew! I decided to end this session and distract myself for a while. I partially cleaned up and started doing some homework. A couple hours later, with a lot of time before Susie got home, I felt I could try again.

I returned to the bathroom and sat once again with back against the tub. I really wanted the dildo in me and was going to take my time so it would work. My horniness wasn’t going to be stopped from some of the pain I felt a couple hours before. I prepped the dildo with KY and stuck a couple fingers into my already slick hole to get some anal lube. There was just enough to spread on my hole and the dildo.

This time, my ass seemed very sensitive and slightly more open as I was able to start with two fingers, and a part of a third going in me. This looked so hot as looked over my dick and watched my fingers disappear into me, over and over. My hole started to open on its own like it was trying to suck on my fingers. I obliged to get all 3.5 inches of fingers into me without issue. I started attacking my hole with abandon with that sloppy sound turning me on and causing a frothy mess on my ass. I was so turned on my dick sprang to life and started leaking after a minute or so. The paper towel under me became soaked with lube and juice. I almost forgot about the dildo when I grabbed my cock with the other hand and started stroking while my fingers were pumping my willing ass. I leaned forward again and sat on my fingers and this time, with no pain, I tried to wiggle them inside. Wow, I was able to move them around with no pain and yet had new feelings that weren’t great, but still felt naughty!

Pulling my fingers out I focused on stroking myself to completion adding the lube mixture to my cock for slickness. I paused a moment and sat back against the tub and grabbed the dildo lying next to me. With my hole already open as if it was waiting to receive something, I lined up the dildo to my hole once again and it slid easily in about four inches before it was halted by a constriction. I was so hot, flushed, and aroused at the sight of this rubber dick entering me that far that I let go of it and stroked my dick twice before it hit me like a brick – slam! There was no build up, I just started to shoot cum onto my chest and my shoulder. I closed my eyes as my sphincter contracted around the dildo with each pulse of my surprising orgasm. I stopped everything while the orgasm seemed to go on and on. I wanted all these feelings in my cock and my ass to never stop. I started seeing flashes of sparks through my closed eyelids while my mouth was open with a breathy groan that wouldn’t stop. Though my orgasm seemed to be a bit stunted with my hole open around the dildo, I had never experienced an orgasm with what felt like a small log that was stuck between my insides and the outside world. I felt each pulse around my ass hole as my dick twitched. After the orgasm stopped and I calmed down, I wanted to cum again but needed to regain my senses first.

I opened my eyes and saw the cum all over me. I wasn’t into eating my cum or precum at the time. I had tasted it during puberty (who didn’t?) and thought it was too salty and spunky. So, I cleaned up what I could with some paper towels. Oddly the dildo wasn’t going anywhere due to my ass’s hold on it, but I started to pull it out which kind of hurt. As soon as it was clear of my ass I gasped a bit as my hole gaped for a few seconds before closing. I didn’t know what was going on with all these new physical things feelings, but my ass had a mind of its own and it was good.

While cleaning up the bathroom mess my dick stayed mostly hard, and I felt the need to go further and deeper with the dildo. Why? I don’t know but knew I wanted more right away. So much for homework!

I laid more paper towel on the floor and lubed up the dildo yet again, but this time I sat on my heels. I rose up onto on my knees, positioned the dildo to stand on the floor under my hole and sank back towards my heels. With barely any resistance my new rubber friend literally popped slickly in and got sucked upwards 4 inches! “Oh my GOD!” I moaned as I felt every inch and every fake vein sliding into me.

I continued sitting back on my heels to 5 inches of dildo and once again felt the blockage inside me. It was uncomfortable as there was a pushing of something inside me. I was flushed and in heat like a cat when I looked down and saw another inch travesti istanbul or two of the dildo still outside me. I wanted all of that rubber pole in me, but it just wouldn’t go further without feeling discomfort.

My knees started to get sore so to alleviate them I leaned back to take pressure off them by putting my hands on the floor behind me. Hmm, I felt a new tingle that made me feel I needed to pee as the dildo press toward my front anal wall, but I ignored it to continue what I was doing. (It was the same feeling when I had two physicals as a teen for a prostate check. Little did I know those exams weren’t needed at that age. I also learned more at a later age that feeling of peeing and what it was about. It will be included in future stories.) I then leaned left to steady myself so I could grab the countertop with my right hand and move to a different position. This caused a shift in the dildo, and my gut, and with the sudden movement of the dildo I felt a weird release inside me. Not realizing what happened until I made the next movement, I rocked back on my heels towards my right, but my right ass cheek missed my heeI and I sat on the rest of the dildo! With a little concern, but a lot of new feelings, a gasp left my mouth and my colon felt like it wanted to push out whatever was there. This opening of my rectum felt so good that when I lifted slightly, I instantly felt every inch of my canal and wanted to instinctively start bouncing on that lovely rubber cock. OH MY GOD, with little movement up and down, maybe an inch, felt incredible!

I straightened myself a bit and felt a little shifting inside me. I thought as an instinct, “I must have rounded a corner inside.” Knowing little about the colon I figured I must be at the large turn of the intestine before it straightens out to the exit. I just knew it felt oddly uncomfortable with a slight pressure on one side of my gut, but it was also a good, full feeling. I felt a heat and flushness starting to build with a level of arousal I never felt before. I could feel my insides hug and caress the entire dildo and it was delicious!

I started to move my ass slowly in a gyrating and wiggling way since the up and down wasn’t as good. I was getting used to having my canal open as it started to hug the dildo a bit better. That feeling of something inside and deep, probing, circling and being stroked internally I’ll never forget. My dick was painfully hard sticking out just begging to cum. I immediately started jacking off and writhing my ass hard on the dildo and within seconds I started to cum. I felt a deep throbbing wave inside me and after two pulses from my dick, I shot my first load about three feet across the bathroom floor and the next was two feet. As I pulsed more and more, I kept cumming in slow spurts over my hand and thighs and didn’t want it to stop.

A few more seconds and I became too sensitive all over, a bit shaky, and out of breath. I looked down as I came back to reality to see my ass constricted around the dildo. It was so hot to see my inner ass cheeks squeezing the cock that I wanted the real thing, soon. I was still feeling the throb of my anal ring wanting to close, but the dildo kept my hole open while I recovered. I was a bit sore but loved the opposing feelings of a dick that wouldn’t fully deflate and my hole pulsing open and closed.

Completely spent I lifted myself up off my new rubber friend. It resisted at first, but its own weight made it fall out with a thud on the floor. As soon as it released, my hole stayed open and dripped lube and my natural juice into a puddle on the floor, it didn’t constrict like before. I also felt the need to push out and expel the dildo that was no longer impaling me. My ass was pleading to be stuffed, but also to instinctually have a bowel movement. I noticed a tinge of blood, but nothing serious like the previous carrot time; still, it concerned me, and I got nervous.

As I stood up, the urge to expel went away. I cleaned up the cum on my hand and groin, the puddle of lube and juice surrounding the dildo and took a quick shower. I put the dildo and KY back in my car’s spare wheel well and thought, “What did I just do? I don’t know, but I gotta try again … when I’m not sore.”

Later that evening, my ass throbbed with soreness, and over the next few days I couldn’t try the dildo again even though I wanted to. Still, my hormones raged like never before and just the thought of what I did and what I could do with Glen translated into an almost constant aroused state the rest of the week through the weekend. I ignored self-anal for a while and only flirted with Glen when I worked. But the side benefit of my constant aroused state was that it led to great sex with my wife over the next couple weeks. During the day I only thought about Glen and plotted our next encounter. But, at night I was only focused on my wife and the sex we would have. I was living a double life, and while I seemed fully present in each, I knew I wasn’t.

To be continued …

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