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My First Orgasm (Embarrassingly Hilarious)

We’ve all been there, the pubescent hormone ridden preteens/teens unsure what these new feelings are. For me I was twelve years old when I first discovered the little joys of pressing my hard cock up against anything and everything. Before we get to the moment of my first orgasm I want to discuss some really embarrassing things I did before discovering masturbation. Oh god they’re embarrassing but I think we’ve all been there. I’ve always been open and honest with my readers so why pump the breaks now.

The first time I decided to be a little deviant was in the bathroom. I can’t remember what sparked this sudden urge to be naked, but it was a thrilling feeling. I stripped down and sat on the side of the bathtub with the porcelain between my legs. The tub was cold when my testicles first touched it, then I pressed down my hard cock onto the side of the tub before leaning forward to put all my body pressure on my throbbing cock. I was in puberty bliss.

The most embarrassing moment of all was the stuffed bear incident. One night after everyone went to sleep I had a “date” with my stuffed bear. Now I’m not talking about a small teddy bear, this was one of the large ones you could win at a carnival. I remember climbing out of bed on the dark and going into my closet to find it. I brought it back to my bed and fucked the shit out of it and that isn’t a figure of speech; there was stuffing everywhere. I fucked that bear in every position I could think of and just the friction against the head of my cock was enough to make me happy. Strangely I clearly knew what sex was, yet I had no idea what cumming was yet. That discovery would come not too long after.

It was years ago and I can’t remember where I discovered masturbation. I’m sure I just realized that tugging on my genitals was doing much more for me than any stuffed bear or bathtub could ever do. This is one moment I remember vividly. I was tugging away when suddenly this strange alien like feeling came over me. My chest tightened and I panicked! I stopped what I was doing and waited to calm down. I was terrified I thought I was going to have heart attack and I’d be found dead in a compromising position. Little did I know I was on the brink of my first orgasm. I touched the tip and felt precum. Idiot me thought that must be the cumming we learned in sex education. I figured the precum was the grand finale.

The next day I was sitting in my bean bag chair. I was big into the WWE (World Wrestling Entertainment) at the time. I was reading through a magazine and the last page always featured a diva – “divas” were what they called the women’s division at the time. There was Christy Hemme in a bikini with pie on her ass. My heart was racing and maybe this is where my infatuation with asses began? Funny enough I came across this magazine under the stairs. I took a photo and attached it below. It wasn’t much, but at that age it was more than enough as I felt myself grow hard.

DSC00048 (2)

I made a commitment in that moment, I didn’t care if it killed me; I was going to push past the “heart attack”. I was prepared for the little bit of precum that might come out again. I had a tissue on my stomach and I began masturbating with an end goal in mind. That feeling came upon me again. I felt worried again but didn’t stop. Suddenly my ass clenched and my testicles felt like they were lifting inside of me as I dug the heels of my feet into the rug. Like a shot of lightning I felt the release I had always wanted yet didn’t know existed. I came and I came hard. Streams of cum shot onto the tissue as I held it up to catch everything; nearly ripping right through the thin material.

I had discovered the pleasures of orgasm thanks to Christy Hemme. A few years later she posed for Playboy and I got plenty of use out of that magazine. A whole new world had opened up for me and I kept it a secret. In this little world I figured I was the only person doing it when in reality nearly everyone was doing it – especially those of the same age. I felt like such a deviant as if this was my rebellious phase; boy did I have some learning to do. I still remember the first time I discovered I wasn’t the only one with this secret and I remember the first pornographic video I watched, but that is a story for another time (plus some research, maybe I’ll be able to find that scene). Masturbation is one of the few things I enjoyed doing when I was younger that I still enjoy doing now.

Until next time… Happy cumming,


#7 Anal Sex (w/ Bonus List Item)

This by far was the most anticipated item on the list. It was something that had been spoken of since I was in my teenage years; something I had seen in many pornographic videos. The fact I was an ass guy had me naturally drawn to the idea of anal. I had read horror stories about it, but that never deterred me from the fact I wanted to one day try it. The other night was that night.


“J” and I always discuss the list before having sex. Some nights we just don’t get around to anything on the list because we get caught up in the moment and prefer to continue doing what we’re doing instead of trying something new. Anal was always brought up, but neither of us had made the move or suggested it during sex. Finally when “J” asked me what I wanted to do because it was my turn to pick, I jokingly said “how about butt stuff?” as we laid naked on the bed after our first round. “J” agreed to my surprise and suddenly I was excited but a bit nervous.


“What position should we attempt it in?” I asked. “Bent over,” she replied. I got off the bed and rolled on a new condom. A small bottle of anal lube that had been used for “J’s” sensual hand jobs was about to be used what it was made for as I grabbed onto it. Standing next to the bed she played and squeezed my testicles, until I asked her if she was ready. Sitting up, “J” positioned herself on all fours on the bed; presenting her ass to me like an animal in heat. I climbed back onto the bed and inched my way behind her only to realize this position probably wouldn’t work for our first time.


I climbed back off the bed and grabbed onto her hips, pulling her back over to the side of her bed until her feet planted down on the hardwood floor. She remained leaning forward with her face buried in the mattress as I took charge of the situation. I drizzled some lube into my hand and stroked my condom wrapped cock; making sure to coat it thoroughly. Spilling more onto my fingers, I applied lubricant between her ass cheeks; over her anus. I rubbed the rim “J’s” ass for a few moments feeling each wrinkle on her new entrance.


“Here I go,” I said. I knew this wasn’t like you seen in pornography, where they guy just jams his cock in a girl’s ass and she moans in pleasure. This was a first for both of us so I eased my way into it. Rubbing the head of my cock against her anus I started to push forward, but unfortunately I slid away. It was tougher than I thought it would be entering her. Again I tried, this time I felt the head of my cock slowly sliding in. I asked her if she was okay and she said she was fine through gritted teeth.




Eventually as her clenching anus relaxed I slide in a little bit more at a time. In fact I slid so slowly inside her that I wasn’t sure if I was moving in deeper at all until I was balls deep in her ass. I looked down at the two arches of her ass and couldn’t believe we had finally accomplished this item on The Fucket List. I moved my hips slowly, feeling the rim of her anus grip onto my shaft and slide up. In and out I went at a very slow pace until I could feel myself fucking her without as much force. I thrust into her harder and faster; her ass cheeks rippling with each pound of my hips.


Now here is where it gets a bit interesting because I didn’t feel much of a difference. I get that the anus is tighter than the vagina, but for me I thought to myself, “what is the big deal?” I think anal was a bit over hyped for me, or I couldn’t feel the difference because I was wearing a condom. I continued to fuck “J” from behind, but soon pulled back and allowed my cock to pop out of her anus. “How was it?” I asked. She explained it stung a bit, but she was fine. “J” had a new found lust emulating from her, she pulled off my condom quickly and pushed me down to her bed on my back. Rummaging through her dresser she found a new condom and immediately rolled it down over my shaft as soon as the packaging was off.


“J” climbed on top of me and I entered her with ease from how wet her cunt was. The two of us managed to find the perfect position like we never had before. I was a bit lower on her body with her breasts nearly bouncing against my face. I clutched onto her thighs as she rode up and down and her breathing got heavier. I put my knees up and planted my feet in her bed and thrust up into “J”. The two of us were now drenched in sweat and as I thrust into her there had been so much cum that the sounds of liquid smacking against skin echoed through the bedroom. I always enjoyed a mess; the messier the better I say and this was the messiest the two of us had ever gotten.


I continued thrusting up into her at the same pace and could feel a tingling sensation in the head of my cock. That feeling gave me the boost I needed to finish “J” off as her breathing stuttered and she lifted herself up far enough so that I could slide my fingers into her until she came. I felt a sense of accomplishment after this session. She lifted herself up and our skin peeled off one another from the intense sweat we created. I had never seen her squirt before but it seemed to have happened this time as the sheets of her bed were literally sprayed with cum. It was a night to remember for more than just the anal.


I laid back down on the bed because “J” was deadest on getting me off. She used some of the lubricant to stroke my cock and I swear this was the closest she came to getting me off. Unfortunately my body hates me and I lost that feeling of close to cumming. She asked me where I wanted to cum on her because then we could cross something else off the list.  I said her breasts with the plan to masturbate until I was close and jump on top of “J” and cum all over her breasts. She had other plans, I got to the point of no return and she lay next to me on the bed and put her breasts right in the line of my orgasm. I came hard and streams of cum coated her breasts; trickling down over her nipples. Like I said, it was a night to remember.


Again I must say that anal for me didn’t live up to the hype and was really not worth the extra effort. Although I would like to try it again someday without a condom to really be able to judge. This experience was in by no means a bad one, it was good but just not great if that makes any sense. “J” wrote her own perspective on this night and if you’d like to read is click here:




Until next time, happy fucking!


“J’s” Perspective: Anal Sex

Hello fellow sex fiends, “J” here again!

Tonight for the first time we tried anal… Surprisingly enough, I enjoyed it.

At first it was tough and it hurt, but once Mike was able to adjust himself into me, it felt good. As he thrust in, I could feel my muscles from my thighs to my belly button contract, it was intense. As he slid out I could feel the head of his cock slide down my anal cavity – oh the goosebumps.

Eventually it began to sting a little so I had to slowly slide out, but it was a marvelous first attempt. I turned around and stood facing Mike, I could see the secretions from our previous act making the hair on his testicles stick together. That turned me on, so I did what any woman in my position would do, I grabbed his cock and removed our used condom, slid a new one on and pushed him down to the bed.




At this point I couldn’t keep my moans silent anymore, I wanted him so badly. Every thrust made me want to feel him even deeper inside my soaking wet cunt. And then he slowed down, “Oh No!” I remember saying and he began to fuck me in perfect rhythm. Making the walls of my vagina contract, I was about to have an extremely intense orgasm. I could feel the build up and he stopped. This time I begged, “no, no no” and held onto him. He slid his fingers inside me and furiously rubbed my clit and “g” spot.

I couldn’t contain it any longer. My back began to arch and I couldn’t muffle my sounds no mater how hard I tried. The build up was so intense I didn’t know what to expect. After my vagina contracted more times than I can count and I came over his fingers, I rolled over and collapsed. That was it for me… But not for him!

It was time for him to cum on me somewhere, but that part of the blog is for Mike and hopefully his interpretation of this evenings events.

Happy fucking, y’all,

– “J”


CLICK HERE: #7 Anal Sex (w/ Bonus List Item)

#86 Sex On A Car

This is my second story involving a car and things worked out better; surprisingly much better. It all started when “J” and I were hanging out at the beach with my friends as the sun set. It was a beautiful night and we all ended up having a good time. Once the sun set, we all went out separate ways with “J” and I climbing into my new Ford Fusion and by “new” I mean new to me because it is a used car. I’m getting a bit away from what you really want to hear about, but detail is key and it’s important to know what car it was because of the curvature of the roof. We’ll get to that in a moment.


“J” and I took the back roads home, no reason except we were enjoying the drive. Suddenly she reached over and began rubbing my crotch; my cock growing hard with anticipation. Unbuttoning my jeans as I drove, she guided my erect cock out of my fly and slowly stroked me. The back roads we were on were lined with rich homes on the beach so there are many stop signs along the way. One particular stop there was a couple walking along the side of the car and “J” did her best to cover me with her hand but it was still obvious what was going on. Luckily I drove off before they could get close enough to look into the car. We both laughed it off and she immediately went back to playing with me.


The road has no street lights; the moon and the odd house light were the only sources of illumination after my headlights passed. I couldn’t take it anymore; I wanted more than just a handjob. We came upon a street with a no exit sign and followed it right to the end. It stopped at the start of the beach and we were in between two large homes; both in the dark. I turned off the car and began kissing “J” with her hand still tightly gripped around my cock. I began to tug on her black tights, trying my best to get them off from under her ass. “J’ helped and slid her pants off and of course she wasn’t wearing any underwear.


I rolled a condom on, lowered her seat back and climbed on top of her in the passenger seat. I tried my best to work my way inside her but was failing miserably thanks to the limited space; plus I felt like I may have been suffocating her. That’s when the idea sparked; it was dark so why not try crossing something off the list. I told her to follow me and opened the car door. Unfortunately that made the light come on and if anyone had been nearby they’d see my bare white ass backing out of the car. Once we were both out and the light had dimmed we made out; the two of us both pants less but still with our tops on.


“J” grabbed my cock again and guided me towards the beach. We considered crossing off sex on the beach but it wasn’t meant to be that night. I brought her back to the car and bent her over my hood; her bare ass and cunt presented to me under the moonlight. I quickly forced my way into her and began pounding into her. My cock slid between the lips of her cunt while the clap of my thighs against her cheeks rung out into the quiet night. There we were in the middle of a residential area fucking. Every now and then I would slow down as headlights passed a few streets away.




Having “J” bent over was working fine, but it wasn’t technically “on” the car. I told her to turn around and sit on the hood. I helped her up as she planted her bare ass cheeks onto the hood of my car – I could think of no better way to christen it. She laid back, her head on the windshield and her legs spread. Little did we know that the hood of my car was angled perfectly for sex. I slid my cock back inside her with ease. We began fucking again; her head was tilted backwards with her eyes nearly closed. I watched her breasts bounce inside her top and quickly lifted her shirt up. Her breasts were riddled with goosebumps in the cooling night air. I grabbed onto her breast while my other hand clutched onto her thigh to ensure she didn’t slide too far down on the hood.


“J” eventually came; sometimes you can’t tell when she’s orgasming because she’s quiet. This time I could feel how wet she was as her cunt contracted around my shaft like a heartbeat. After a few moments of catching her breath, she wasn’t done with me. We climbed into the back seat and sat on my lap facing me. We continued to kiss, our tongues pressing against one another in a battle of dominance. She reached down and guided me back inside her. “J” begins moving her hips, grinding on me while I was balls deep inside her. We were dead center in backseat, so she leaned back between the driver and passenger seats. She looked amazing with her body stretched back as she continued riding me.


Once the two of us were covered in sweat and breathless we came to a stop. My lap was drenched in her juices, just how I like it. We both got out and changed right there in the street; it was much easier to do so and wasn’t the worst thing we did on that street. The experience still remains strong in my memory as I’m sure you can tell from the small details I can still remember from something that took place nearly a year ago. If you have the right kind of hood, I highly recommend trying this. “J” and I have discussed doing this again this summer; that’s how much we liked it. Get out and try it! Let me know how it went for you and maybe we’ll feature the story on the blog.


Until next time, Happy Fucking,


#16 Car Sex

The classic go to spot for teenagers who don’t have a place to actually go. The back seat of the car is synonymous for sexual activities and unfortunately I never experienced this during high school or in my teenage years. In fact, this took place over a year ago and was also the first time I ever had sex with “J”. What do you say we get right into this hot and a little bit comedic story that took place on a hot summer’s day.


“J” and I had met on Plenty Of Fish and we had fooled around before, but mostly the two of us getting handsy. We had been talking about sex for six months it seemed, before I finally agreed to meet up with her, but we still had no plan on where to go. I picked up “J” in the afternoon and she directed me right across from her street down to the bay where we found our soon to be go-to-spot. It was a narrow dirt road that had a wooden fence on one side and unfortunately a chain length fence into someone’s backyard, but we had wanted this for so long, the risk of being seen was outweighed by the lust we had for one another.


I parked my car the same way I had seen every guy do in nearly every teenage comedy. “J” wore a short dress with no underwear for quick and easy access in case we had to cover up quickly. Again it would be our first time so I was a bit nervous and I’m sure she was as well. I leaned over and kissed her before running my hand along her bare thigh. I could feel myself growing hard just by the soft touch of her skin. Reaching up her dress I felt her wet cunt and began rubbing her clit while every so often looking over her shoulder at the house who had a clear view of us.


Bear with me because it was a while ago so I don’t remember every little detail. One of us suggested making our way into the back seat. I unlocked the doors and we climbed out and into the back. One important detail you should know is, at the time I drove a 2004 Ford Taurus which I unfortunately had to say goodbye to a few later. Now for those of you who don’t know much about cars – myself included – the Taurus is a fairly small four-door car (I think you can understand why this detail is important).


We sat next to each other in the black car that was quickly turning into a sauna thanks to the sun beating down on it. I had mentioned I wanted to go down on her so I figured this was as good a time as any. At the time I was a bit worried because in the past I hadn’t had good experiences with going down on women, but that is a whole different story. It felt like a lump in my throat as I made my way down between her legs. There was no room; I ended up opening the back door and stretching my legs out so I could get myself in a better angle. To my surprise she tasted good and all my doubts of enjoying oral sex had washed away and I felt a sense of relief.




It had been a while since I had sex, so the smell of sex between her legs was inviting to my lungs. The two of us were starting to get a bit sweaty from the heat, despite the windows and one door being wide open. “J” positioned herself kind of on her back and she looked completely uncomfortable but never complained. I took off my pants as my hard cock sprung from my pants. I took a condom and rolled it on as I looked at “J” presenting her cunt to me under her sundress. She quickly took it off until she was completely naked and I did the same. The two of us were now completely naked in the middle of the day in the back of my car.


I was nervous about being caught and it I think it showed because I spent a good amount of time looking out the back window. One funny thing that came out of this was I positioned myself between her legs and stared out the back window. I rubbed what I thought was her wet cunt, as it turns out we both covered in a layer of sweat so I mistook her wet cunt for her wet anus. I don’t know exactly what she said, but I remember her expressing the fact that my fingers had gone further south than expected. The two of us burst out laughing and I was amazed I couldn’t feel the difference.


After our quick laugh we quickly got back into it. I guided my cock inside her and she sexually closed her eyes and I buried myself inside her. I began thrusting, but not too hard because her head was pressed up against the window. The whole situation was uncomfortable, but the feeling of us fucking was enough to overlook how bad car sex was in a small car. We eventually switched positions. I sat down and she sat down on my lap; gripping onto my cock and directing me back between the lips of her cunt. The sweat was trickling down her back and it only added to the overall sexiness and excitement of what we were doing. The sounds of her ass cheeks spanking down onto my thighs echoed through the car as our flesh peeled off each other with each movement of our bodies.


“J” came and I can’t remember if this was when I explained I had a tough time finishing or we had discussed that prior. Either way I enjoyed myself and we never got caught. I climbed out of the car, the slight breeze was greatly invited and swept between my legs as I tried putting my clothes back on as quickly possible. The two of us spent so more time down by the water before I brought her home.


Overall the experience was fun because who doesn’t enjoy sex with a hot, curvy girl, but as far as car sex is concerned … I wouldn’t be disappointed if it never happened again, but I’m not against it! Especially when it comes to sex ON the car, but that is a story for another day.


Until next time, Happy Fucking!


Trojan Bareskins – The Best Condom On The Market

When I first started this blog it was meant specifically to tell the stories of my crossed of “Fucket List” items, but over the past few months it has evolved. Of course I’ll still be telling those stories, but there has been a larger spectrum of content lately, steering this sex blog into a direction that I’m excited and happy with and I hope you are as well based on the number increase behind each new post, I’m assuming you are? The reason I mention this is because this post will be The Fucket Lists first ever product review. Shall we get on with it then?


Let me start out by saying I am not being paid to endorse this product, nor was I sent it for review purposes. Trust me, we’re not at that level and if we were to receive anything, you’d be the first to know in a brag-like fashion. No, this all started when “J” and I ran out of condoms. It was a cold winter’s night when we walked down the street -opting not to take the car – in search of condoms. The gas station unfortunately didn’t have any, but too our luck, the drug store was open for another ten minutes. We made our way in straight to the “family planning” aisle and started our search for something new to try. To our surprise there was a Trojan package that featured four different kinds of condoms. Why not try them all? We thought as we paid for them at the counter. “J” wondered if the guy behind the counter was thinking we were on our way to fuck. I know many guys are embarrassed to buy condoms but strangely I’ve never had any problems with it. I say this as a usually anxiety-ridden person.


We got back to her house and began reading about each condom. Some promising “her pleasure”, while others mentioned their rippled design. (Side note, this was actually the night we crossed off “Shower Sex” off the list). I honestly can’t remember which one we tried first, but it wasn’t all that good. It wasn’t until after the shower that we ripped open the “Bareskins” condom. I’m not claiming to be huge, in fact I’ll be the first to tell you I fall under the average category, but this condom fit snug around my shaft. The latex was thin enough to give me more of a sensation than the average condom. It was almost as if it was designed for my cock.


“J” liked the Bareskins condom as well, commenting “it feels like you’re not wearing a condom” as she rode me. It was the closest to no condom as you can get and as a result, we had some of the best sex we’ve ever had that night. After sex, “J” stroked me with the condom still on and I could feel the naked sensation of my sensitive head being rubbed. The two of us were in such awe of the condom we found, we took turns feeling it on my cock – coated in “J’s” cum – before taking it off to finish the job… no pun intended… Alright a little pun intended.


Now of course I haven’t tried every condom that exists, who has? But, Trojan Bareskins is by far the best condom in my opinion. I would give it a five out of five stars. Actually, scratch that, this is a sex blog. We should have a custom rating system aside from stars. I give this product a five erections out of five. Run out, pick up a back and get your fuck on. Happy Fucking Everybody!


PS. Send me free stuff Trojan!