Gay Stuff : What Was Your First Time Bottoming Like?

My first time bottoming was with very sexy black guy that I had known from work. Went over to his house and his partner was there who is a bottom he helped coach me through the breathing and relaxing it was fantastic felt great . I went from a top to versatile Ian have not looked back it’s great

Anaconda,Nickiminaj HE MADE ME THINK IT WAS WAR…LOL

I actually wrote a story about it for another site. Here it is, if it’s not too long:

First Time on Bottom

I got an email from Ralph one day a few years or ago. “wanna play?” is all the email said. Ralph and I have known each other for a while and an email was how he usually contacts me.

“Sure. What time?” I emailed him back. Ralph lives in a nearby town. He, like me, is retired and we both have a lot of time on our hands. But Ralph is usually tied town at his house caring for his cancer-stricken wife (he says, anyway) and is only able to get away for a couple of hours when is wife goes to the doctor for an appointment. When he does, he usually just wants to come to my house for a quick blow job and then, as soon as he cums, he leaves. Not having much going on that day, I emailed him back with that message.

I only had to wait a few minutes before another email came in from him. “One o’clock?”

“OK,” I emailed back. “See you then.” It was our usual practice. Ralph doesn’t have his own computer or a cell phone and the terse messages (which he sent from a computer at the local library) were the way we communicated. And those terse messages were similar to the way our sessions together went. Ralph would come in, maybe engage in a few minutes of conversation (which often detailed his trips to a local adult arcade) and then we’d repair to the bedroom. He would take off his shoes, pants and underwear (but never his shirt) and lie down on the bed while I stripped down. I would then go into the bathroom, wet down a washcloth and wash off my dick and scrotum. Upon re-entering the bedroom, Ralph would move to the edge of the bed, on his belly, and then proceed to take my dick into his mouth and suck on me for a while. Then, after he had sucked me nice and hard, I’d lie down on the bed next to him and we’d sixty-nine. After a while, Ralph would usually stop sucking on me, though, and I would be able to concentrate on getting him off. It usually didn’t take long before I had him moaning and ready.

“I’m gonna cum,” he’d tell me. “I’m gonna cum. Oh. Oh. Oh!” And then he’d squirt. I’d swallow his jism and then lie back as Ralph would recover for a while, then he’d sit up and begin getting dressed again.

I’d often tried to get Ralph more romantically involved in the process but he really didn’t seem interested. He did let me kiss him a few times and even though he’d kiss back, he did it without much enthusiasm, it seemed to me.

No, all Ralph was interested in was getting his rocks off. Wham, bam, thank you, man. (I know that usually ends in “ma’am” but I’ve never thought of myself as a “ma’am.”)

Of course, since I didn’t often have much opportunity for any other type of sexual activity, I was happy to oblige. Since my wife’s hysterectomy (which caused her to lose all interest in sex) I don’t have many outlets. Since I’ve been bisexual for a long time (my first male-to-male contact occurred when I was 21—I’m 68 now), my attention gradually drifted toward men. I don’t cruise gay bars or adult book stores very often, but do use the internet sometimes to chat with other men. But usually, the men I chat with are so far away from where I live in El Dorado, Kansas, to make actually meeting these men either difficult or impossible. But Ralph lived in a nearby town, which allowed us to connect.

Yet even though Ralph was not usually very communicative, I had gotten the admission out of him once that he would like it if we could get another person involved in our sessions. I think he was hoping my wife would join in, but I told him there was just no way that would ever happen.

But then, luckily, as I was waiting for Ralph to come over (it was about 11:30 at the time) I got a telephone call from another friend of mine. “Hi, Duke. It’s Jay. I have a doctor’s appointment at twelve o’clock. Would you mind if I came over afterwords?” Jay’s doctor’s clinic is only a couple of blocks from my house.

“Uh, that would be fine with me,” I told Jay. “But I have another guy coming over about one o’clock. Do you think you’ll be done at the doctors by that time?”

“Sure,” Jay said. “I’m really just giving them some blood. They put me on a new medication and they just want to do some blood work to see how I’m doing on it. I should be there about that time.”

“Good,” I told him. “We can make it a three-some.”

“Great! I’d love that!”

“OK. See you about one.” Cool, I thought. I hadn’t been involved in a three-way for a long time. I was really looking forward to the encounter.

Jay was another acquaintance of mine. We had originally met online a few years before. Jay was younger (mid-thirties) and we had a few nice sex sessions together at that time. But Jay soon met another guy who was interested in a long-term relationship and he moved in with him at a house in Wichita (about 20 miles southwest of El Dorado.) But unfortunately, Jay’s partner was diagnosed with lung cancer and after a two-year battle with the disease, passed away a few months before. So Jay, who is a licensed practical nurse, was then able to find a position as a live-in nurse for an elderly woman in El Dorado who was suffering from Alzheimer’s. But Jay had his own medical problems. He was a diabetic and was on medication to control that. But evidently a new medication he was taking needed monitoring and that led to monthly visits to the doctor’s nurse to give a blood sample. Twice before Jay had called me prior to his appointment to see if we could get together for a while afterward. During his appointments, the neighbor of the woman he cared for would stay with her for a couple of hours while Jay was gone.

Anyway, that was the scenario for the day. I took a shower about a quarter after twelve and was just lounging around the house in my robe when Jay showed up about five minutes to one.

Jay, like I said, was younger and had a nice, slim, muscular figure. He was a good lover, too, with a medium-girth 7-inch dick. When we had played together before, we had limited ourselves to mutual oral at first but, since his orientation was primarily as a bottom, Jay had wanted me to fuck him. I tried a couple of times to top him, but due to the indisputable facts that I have multiple sclerosis, which has weakened my muscles and robbed me of stamina, a big belly and a short dick, it was kind of difficult to get and maintain good penetration that way. We had better luck with me lying on my back and Jay impaling himself on my erect dick, then working from that position. That was a lot of fun.

It didn’t take long after Jay got there for Ralph to finally show up. Jay and I were still standing in my living room, talking about his job with the old lady and his treatments at the clinic when Ralph arrived.

“Hi, guy,” I said as I opened the door and let him in. “I hope you don’t mind, but I invited Jay over to join in.”

Ralph smiled as he looked at Jay, then back at me there in my robe. “Gosh, no,” Ralph said. “The more the merrier.”

“OK,” I said, very pleased that Ralph didn’t object. “Why don’t we all go into the bedroom?”
Once we arrived in the bedroom, I lowered the blind on the window and pulled the curtain as Jay and Ralph stripped, with Ralph leaving his shirt on, as usual. I stripped down and went next door to the bathroom to wash down my dick, scrotum and ass quickly with a wet washcloth. Why I did that, I don’t know. After all, I had just showered.

When I returned to the bedroom, I saw that Ralph and Jay had started without me. Jay had Ralph’s rather short, but thick penis in his mouth and Ralph had his lips wrapped around Jay’s dick.
“Can I get in on this?” I asked as I lay down across the head of the bed.

Ralph broke off the contact with Jay’s cock and moved over to where he could reach my now-hardening penis with his mouth, and Jay repositioned himself to where I could now suck on his substantial meat. So, there we were, each sucking a dick in a circular configuration on the bed.

I was really enjoying the whole thing, but after a few minutes, I felt Ralph break contact with my dick and he laid over on his back. I knew he was probably close to cumming as Jay sucked on him and, sure enough, soon he was groaning and saying. “Oh, yeah. I’m cummin’. Cummin’!”
Jay just kept on sucking as Ralph shot his load, with Jay swallowing every drop.

After he was done, Ralph lay back enjoying the release his orgasm brought. He brought his hands up to his face and rubbed them over his cheeks and forehead. Jay let Ralph’s quickly-softening dick fall from his mouth as he lay back on the bed. I had to quit sucking on Jay’s nice cock because I knew Ralph would be wanting to leave now that he had shot his load. And sure enough, it wasn’t long before he sat up on the bed, then reached down to the floor to retrieve his clothes.

I looked over a Jay and kind of shrugged. “Ralph doesn’t usually hang around very long,” I told Jay.
Soon Ralph had his clothes back on and I pickup up my bathrobe, which I had brought with me from the bathroom, and put it on. “Let me let Ralph out,” I said, giving Jay a wink and a smile. “I’ll be right back.”

As I walked with Ralph back to the front door of the house, I thanked Ralph for coming over.

“Yeah,” Ralph said in his usual terse manner. “That was fun.”

“Have to do it again sometime,” I said, unlocking the front door and letting Ralph exit. I watched Ralph walk quickly to his car, get in, then drive away. I shook my head, wondering if Ralph ever did anything in a more leisurely manner.

After relocking the door, I went back to the bedroom. Jay was still lying there, his head on one of the bed’s pillows. I noticed his still hard, his fine 7-incher erection was sticking up in the air.

“Now, where were we?” I asked as I slipped off the bathrobe and lay back down on the bed next to Jay. He rolled toward me as my arms went around him and we kissed.

Soon, though, Jay raised up and changed ends of the bed so we could sixty-nine. I was soon enjoying the feeling of Jay’s strong, smooth-skinned dick in my mouth and he had my little nubbin in his. As I was deviling the head of his dick with my tongue, though, I felt Jay’s hand moving into my ass crack and soon felt the social finger of that hand fingering, then moving into my anus.

Now, a little note of explanation and a small digression. Up until this time, I had never been fucked in the ass. You see, all my life previous to about a year before this time, I was literally a “tight ass.” I had had men attempt to explore my asshole with their fingers but it had caused me too much pain for it to be pleasurable. That orifice was just too tight. So I had always limited myself to either just sucking other guys off or topping them.

Then, about a year or so previous to this incident, my prostate began acting up, big time. It was “BPH” or whatever that thing is that causes your prostate to grow and makes it hard for you to piss. After suffering with this condition for a while (which finally meant me going to the hospital emergency room for someone to catherize me and let the urine flow, then acquiring catheters and lube to relieve myself on my own that way) my urologist recommended I undergo a TURP (that’s a Trans-Urethral Resection of the Prostate). What that procedure entails is placing a rasp-like instrument (some doctors use a laser) into your urethra and reaming out the duct that carries urine from your bladder through your prostate to your dick so you can piss without having to use a catheter. After getting the doctor’s assurance that even though I would be sterile after the procedure, I would still have sexual function, I agreed to do it. Everything went OK, I guess, even though I am now somewhat incontinent and have to wear an adult diaper to catch any leaks.

But what the doctor did not tell me about the procedure was that messing with my internal plumbing like that would leave me with bouts of severe constipation (something about the liquids not being in balance in your colon). And suffer I did. I had a series of very hard, very big stools when I went to take a dump. Some of those turds were so big, they would tear the rectum as they came out, which left little spots of blood behind in the toilet bowl. That was scary, what will all the concern with colon cancer these days, but I had it checked out. No cancer. But it did have one benefit for me. It stretched out my rectum to where I now figured I could take a dick up that way.
So then, when Jay started playing with my asshole (and it now feeling good instead of causing me pain) I thought, Well, it’s now or never.

So I raised up from sucking on Jay’s sweet dick and asked him, “Would you like to fuck me?”

Well, Jay didn’t need any more encouragement than that. “Sure,” he said.

Then Jay turned around on the bed to where his head was now on the same end as mine. I reached over to the nightstand beside the bed where I had a tube of lube. You see, I had been planning on this for a while. I handed Jay the lube, then raised my knees up to my chest as he applied some to his cock and some more to my asshole. I must say that his ministrations on my rectum with the lube felt great, but not nearly as great as when, a few seconds later, he sat up on his knees and began inserting his hard dick into me.

I did feel a little pain at first as the head of his dick pushed past my sphincter, but after that it was pure heaven. Oh, my God, I thought. This feels so GOOD!

Soon Jay was in all the way and then he began fucking me in earnest. With each thrust of his hips, I found new ecstasy. I looked up at him as he thrust away and wanted so very much to kiss him, but he was too busy pummeling me into the surface of the bed. But I loved the look of intense concentration and rapture I saw in his expression. The next thing I knew, I was wrapping my legs around him, wanting to hold him in; wanting this bliss to go on as long as possible. The next thing I knew, though, Jay started grunting a bit with each thrust of his dick into me. I knew he was getting close.

“Oooooooooooooh,” he said as his orgasm began to let go. “Oh, my God!” The last expression coming out in an ecstatic rush of release. I could feel Jay’s cock swell and fill me even more as his semen began to spurt.

Now I really was in ecstasy. I could feel every pulse as his orgasm continued and each spurt and thrust heightened my pleasure even more. Finally, I thought. I finally got a man fuck me! Oh, my God, why did it take me so long?

I lay there, my knees still in the air and my legs still wrapped around Jay’s waist as he collapsed down on top of me. Soon, though, I had to break the embrace of my legs on the younger man’s body as I felt him trying to roll off me. He rolled over onto his side and soon I rolled over into him, too, and we hugged and kissed.

“Thank you,” I said, breathlessly. “That was sooooooooooooo good. So very, very good!”
Jay just looked at me and smiled.

“You know,” I told him. “That was my first time.”

“Really?” he said.

I nodded. “That’s right,” I told him. “First time a guy ever fucked me. But I sure do hope it’s not the last.”

And, luckily, it hasn’t been. But at my age and physical condition, lovers are not quite as plentiful as they could have been if I started doing this when I was younger, better looking and not quite so decrepit. But occasionally, I do manage to find another lover. I just wish I could find more. After all, I have a lot of catching up to do.

my song: Ziggy Stardust. LOL.

My first time was my freshman year in college. Was invited to a frat party. I expecting to see paddles with greek letters and beer drinking. There was neither. One of the brothers offered to show me a paddle in his room. He gave me a back rub that’s when I noticed he was hard then he shoved a large item into a small , tight never before opened hole with a condom but NO LUBE! I tried to stop him and get away from him. He was having none of that. Then it started to feel really good and eased into it.

Ahhhh I remember it like it was yesterday. It was on my 19th birthday. Was running late to my own party. When I got there everyone I know was in the bar waiting for me and they had an hour head start drinking so I had to play catch up. I was staying until closing. Already knew that going in. As my friends departed there were 3 of us left. This older guy found out it was my birthday and ordered a round of beers for my friends and me and he joined us. Not to be rude we invited him into our lil circle. He told us stories of being in the army and cars he had owned. and we sat in amazement. Turned out we drove the same blazer his was newer. We bellied up to the bar and he bought me another drink. This one was different. I remember going to the rest room and he followed me in. We chatted at the urinal. I caught him looking. But I hadn’t had any gay experience yet. Still questioning. As I walked out of the restroom I was stumbling all over the place. He said for my friends and I to hear,”hey this guy needs some fresh air, I’m grabbing a smoke.” They waved is off and called me a light weight. He said come here I’ll show you the newer version of your blazer. Let’s take it for a spin. As we were driving I was falling asleep. I felt so drunk. But I know I could drink twice what I had put down. We pulled into a church parking lot and he pulled out his cock. I remember not being able to move and telling myself to breathe. He forced his cock down my throat. He was rock hard. But I couldn’t breathe. I gagged him out and he got mad. He punched me in the face but I couldn’t feel it. He was getting pisssd. I took an elbow to the eye. I just remember telling myself to breathe. Make your lungs work for you. Next thing I know my door is open and my legs are being pulled outside the passenger door. Off came my shoes then my pants. He started sucking my cock but I couldn’t get hard. I took another punch to the face. I now remember looking up as my head laid in the arm rest and he was trying to get into me. I tried to hold him off but couldn’t move. He was getting mad. He spit on me several times. But I didn’t realize he was spitting into me. He wa stroking and got hard. He penetrated me and began to fuck me. He leaned into the car and kept slapping my face. I remember everytime he’s stop I’d look up. I could see the AAA decal on his sun visor and an angel pin. I kept asking where is my angel. He fucked me what seemed like an eternity. When he was done he put my pants back on and my shoes. Just as he put me up right in the seat and was closing the door a patrol car pulled in. He said to the cop, “ahh this kid just can’t hold his liquior.” The cop replied,”make sure he gets home safe.” I tried to yell but forgot how. Couldn’t form the word. As the cop drove off he punched me in the face hard and my face hit the window. He was nice enough to drive me back to the bar. He dumped me out at my blazer. When he drove off I slid underneath my truck the best I could. Thank god for the 4″ lift. I woke up the next morning. I slid out and found my pager. 5-6 phone number s from friends that saw my truck in the parking lot as they drove to work. I sat there and cried for hours. When I was able to regain composure I got in my blazer and went home. Did everything wrong. Hid, showered, cleaned out, thought of suicide, thoughts of revenge, argued back and forth with myself to call the cops, do I go to a doc…etc. I don’t do anything. I showered 15x that day and there after. I couldn’t get clean enough. Being 100% Italian revenge was my best option in my head. I planned how to get this guy more times than the brinks job.
I waited in that bar parking lot (yes with a gun) every night for 2 months. Then on a Thursday night he pulled in. I so wanted him dead. But I started to cry again and knew I’d kill him. But I didn’t. I went into the bar. Sat right next to him. Ordered a beer. I was so scared. My heart was pounding. He looked at the bartender and winked. I saw it in the mirror. It was then I knew the bartender was in on it. He slipped the roofie into my drink. I struck up a conversation with him and played it off as I didn’t remember him. As I walked out I said,”have a good night guys, good luck with that truck” he said,” yeah you too.” being the star home run king on my soft ball team, I pulled out my baseball bat and took apart his truck. Every piece of glass, every door, 5 tires, the hood and gauges were distorted. I was an animal with a deadly weapon. His truck was ruined. The place he raped me was no longer his safe place. I took back from him. I wasn’t going to be his victim. He changed my life. I was a young weak kinda kid. I toughened up. Never took shot from anyone after that to this day. I’m the lil guy you now dont fuck with. I’m happy with me and how I turned out. Went to many docs and they agree distorting his truck was the turning point where I got my vengeance. It took me a very long time to go back to church. I was staring at an angel on church property while being raped. I had to ask where was god when I needed him. I’ve asked it a million times over. Well I still go to church. I believe God was with me. He kept me alive and kept me from more danger than just taking an unwanted dick. But I’m good now. The guy turned me into a top. Up until 2nonths ago. I met a hot Columbian 6′ 180lbs 8.5″uc, thick, ripped body who speaks seven languages. He’s my new love of my life. He fucks me now and we are vers. Damn can those Latinos fuck!!! I highly recommend trying one for a test drive. But that was my first time bottoming.

I hope The admins dont delet this post. every word of it is true. I hope it may help someone. If you are a victim, don’t let that fucker control you. Take back what is yours.

That question brought back a lot of memories from 37 years ago! My first boyfriend was as inexperienced as I, making for a delightful combination at times.

From best I can recall about 6 months into the relationship Parker wanted to be topped; not knowing a hell of lot — I put a liberal amount of vaseline on my dick and preceded to top him. That did not last long as he came in torrent of jis — covering himself. Parker said it was good — and yes he did get fucked a couple of more times during the next 5 years.

Since turnabout is fairplay — Parker topped me the next time around — with his 7 inches of rock hard dick — with a wicked left curve — he fucked me senseless; we both climaxed within 5-6 minutes. This was long before I know anything of poppers so the pain was extreme to start with. But things definitely got better especially — over the years as Parker became more intune with his body and mine.

In an odd twist — Parker who was bisexual, married the girl he was seeing the whole time he was playing with me. To this day I don’t really know for sure if Parker ever had any other m/m encounters.

My memories of him are all good — especially as a top!