A gay story: Gym Buddy Ch. 03 My name is Jack and this is my story of how I went from straight to bi. I was recently divorced for the second time, a process that drove me into bankruptcy. About the only “luxury” that I allowed myself was a membership to a gym. At the gym, I met Perry. Perry is a black man, slightly younger than my 52 years, about my height (5’10”) and a little lighter (175 to my 185). Perry struck up a conversation while we were working out, and from there we developed a friendship. From the friendship, Perry eventually got me to give him a blow job, then he fucked me. (That’s an awful lot of “from theres, but I can’t recount everything here … you’ll just have to get to the 1st two chapters … Sorry.) His was the first cock other than my own that I had touched since senior year in high school. I never touched that cock like I touched Perry’s.
Perry introduced me to Jimmy, a guy in his 30s, white, about 5’7” tall and 140lbs. I was introduced to Jimmy’s nice looking ass and 7 inch cock later that evening.
While I was waiting for my bankruptcy case to be heard by the court, I was instructed to not work any overtime. All payouts would be determined by my last 3 paychecks prior to the hearing. Once my hearing was held, I was free to work OT if I could obtain some. The OT was going to be my spending cushion.
Finally the hearing was held, and I was able to start accepting OT. While I was enjoying my times with Perry (about every other week, Jimmy would join us), I was missing the feel of a woman. I spent a little money and joined a dating website. After a couple of weeks of writing “witty” letters to various women, I finally had a lady that wanted to know more about me. Her name was Karen. A few emails were exchanged back and forth, and I invited Karen out to dinner. I had done some research of menus, and found a downtown restaurant that didn’t charge a huge amount for an entrée (I found many choices in the $10 to $15 range). Karen and I met at the restaurant, and I found one of the pitfalls of online dating (outdated pictures). I was certain that her profile pics were of her, but maybe 5 or more years old. She was still an attractive woman, but it’s a bit of a shock to see someone that looks different from what you expect.
We each ordered a glass of wine, and got to know each other as we perused the menu. I asked her what looked interesting to her. She replied that she was interested in the Surf & Turf (gulp … I had noticed that and it was over $40). I reviewed my options again, and had seen an item on the nightly specials menu that had interested me. It cost $28, but since I was already overspending, I felt that I might as well order that. I told Karen that was the item that interested me. Karen looked at that and decided to order the same thing (much, much later, I wondered if I had decided on the grilled chicken breast with rice pilaf for $13, if Karen would’ve changed her option to something less expensive … too late for those thoughts). 2 glasses of wine (each), 2 dinners, tip and parking and more than $100 later, the date was over. Needless to say, it was the only date that I went on with Karen. NOTE: those prices are several years old. I realize what a nice night out costs today, but it was a lot of money to me at the time.
A couple of days later, I was at the gym with Perry and Jimmy. In the sauna, I related the story of my “date”, Perry just chuckled. He said, “you know they use us as a meal plan, don’t you?” I told him, “not all women are like that. I’m just not sure how to separate them from the herd.”
Perry laid his head back to the wall of the sauna and asked me what I was seeking? I replied, “well, eventually, sex.” Jimmy stood up and said, “well, if sex is what you seek …” and stood in front of me and took my dick in his hand, leaned over and started sucking me. While most times, we never saw another soul in the sauna, occasionally, we were joined by another guy or two. I was torn between wanting to cum and not wanting to be caught in a gay act in a public place. Jimmy caressed my balls, and worked a finger down near my hole. I saw Jimmy look up at me, and then continued his ministrations on my cock. After another minute, he released my cock and started laughing.
Jimmy said: “You should see the look on your face Jack. It’s like a deer caught in the headlights.” While stroking my cock and fingering the outside of my hole he added, “why don’t we move this to your place Jack?” Perry added that he thought that was a great idea. We got up (me, with my hard on), showered and drove to my place.
I did not have the porn collections that Perry and Jimmy had, so I didn’t pop a DVD in to get us in the mood, but I was still horny from the activity in the sauna. We headed straight to the bedroom. After disrobing, Perry came up from behind me and put me in a bear hug, holding me tight against his body. I could feel his still flaccid cock in the crack of my ass. Jimmy kneeled down and took my cock back into his mouth working me back to hardness. He once again started caressing my balls, then started tugging on them harder.
Perry still had me in the bear hug, and his cock was starting to come to attention. Since he was hanging down when he started the hug, his cock was starting to strain to raise upwards, working its way between the crack of my ass, and it’s shaft being rubbed across my hole. Then Perry found a way to get his hands on my nipples, and he started squeezing them as Jimmy was tugging on my balls. My dick was still in Jimmy’s mouth, but he wasn’t working on it, just holding it there. I tried fucking myself into his mouth, but Jimmy squeezed my balls a little tighter, took his mouth off my cock and TOLD me to let Perry and him handle this.
Perry continued his work on my ass and nips. Jimmy resumed his work on my balls and cock. After a few more minutes of this, Perry suggested that we move this to the bed. Perry released me, but Jimmy kept his mouth on my cock and hand on my balls. Perry knew where my closet was, and returned with one of my ties. He proceeded to blindfold me with the tie. As he did so, Jimmy released my cock and balls, and they moved me to my bed.
They had me lay down on the bed with my head near the foot of the bed, slightly over the edge. Perry rubbed his cock over my lips. How did I know which cock this was? Perry has a 9 inch, thick, black python between his legs. Jimmy is hung well (about 7 inches), but there was no mistaking that this was Perry’s cock. Jimmy lifted my legs and bent them up towards my head and instructed me to hold them there. With this move, my head slipped a little further off the end of the bed.
Jimmy dove in with his tongue and started working on my ass, spreading my cheeks, working his tongue into my hole. I had told both guys that being rimmed was one of my favorite things, and Jimmy was giving it to me good. Perry in the meantime was still rubbing his cock and now his balls over my face. My tongue was busy with licking whatever came near my mouth.
Jimmy was now working my hole with his tongue and his fingers. As he worked a couple of spit lubed fingers into my hole, he took my balls in his mouth, grasping my cock with his other hand. Perry had settled in with placing his balls on my tongue, letting me lick and suck on them. I still had my legs supported by my hands, essentially being bound between Perry and Jimmy.
Somewhere along the way, Jimmy had put a condom on and lubed up and was starting to enter me. He took his time until his cock was seated entirely in my ass. Perry had removed his balls from my mouth and had started kissing me, working his tongue into my mouth. Jimmy started pumping, slowly withdrawing to his tip, then driving into me … each time scooting my head a little more over the edge of the bed. Eventually, my head was not being supported by the bed at all. Perry stood up and placed his cock at my lips and started to fuck my mouth. He started working about half of his cock in and out, while Jimmy continued his thrusting.
Eventually, Perry’s cock was hitting the entrance to my throat. At this point, Perry had my feet in his hands, while Jimmy was holding onto my calves. I was free to do what I wanted with my hands. I placed my hands on Perry’s ass, rubbing those orbs, trying to find his hole. Eventually, Perry pressed forward a little more and for the first time, I felt his cock enter my throat. My hands shot around to his front and pushed back.
Perry said: “Just relax that throat Jack. I’ll be gentle, but its going in.”
With this, Perry pressed forward again, once again entering my throat. I have taken Jimmy to the root, but his cock was nowhere near the length or thickness of the cock trying to gain entrance to my stomach. I tried to relax. I trusted these guys, and I was having fun. Perry pushed, held his cock there for a few seconds, then retreated. He gave me 10 or 15 seconds of breathing time, then started pushing again. This time, it slid in a little easier … and a little further? Once again, he held it there for a few seconds and retreated. Jimmy continued his steady humping of my ass. Jimmy had taken one of his hands and started stroking my cock. I was getting sexual pleasure on multiple levels.
Finally, I felt Perry’s balls on my nose. I moved my tongue around and was able to touch the bush above his cock. Perry was buried balls deep in my throat. If you’ve never felt a BIG, THICK cock entering your throat, you don’t know what you are missing. It is not a sensation that I can properly describe. I knew that I was enjoying it. I couldn’t keep it there for long, but Perry understood this as I would gently push on his pelvis and he would withdraw. He started a steady pumping in my mouth with every fourth or fifth stroke entering deep into my throat.
Jimmy’s pace had started to pick up, thrusting into my ass. Eventually, he thrusted hard and I could tell he was cumming. His thrusts as he came were driving Perry’s cock into my throat each time. Eventually, Jimmy stopped his thrusting. Through most of the fucking, he had held onto my dick, seeming to know when I was on the edge, but never letting me go over. Now that he had cum, he released my cock and withdrew from my ass. Perry took his cock out of my mouth and they managed to spin me around so that now my ass was on the edge of the bed and Perry was placing my legs on his shoulders. He had gotten the lube and was lubing his cock up to proceed to fuck me (NOTE: Perry always fucked me bare and I was fine with that. This is explained in a previous chapter.)
The tie was still around my head, although it had moved so that I could see some beneath it’s edge. I was looking down as Perry was starting to enter me. I saw Jimmy straddle my chest. He had removed the condom and was bring his cum coated cock to my mouth to clean. I enjoyed the taste of Jimmy’s cum, so I readily opened my mouth to clean it. Perry worked his huge cock into my ass and started to pound away. Some days, Perry is able to fuck me for over 30 minutes before cumming (I walk funny the following day), but it only takes him 5 minutes to load my ass today. Because Perry’s cock rubbing across my prostate, Jimmy’s constant edging earlier and my lack of visual stimulation, which seemed to heighten my other senses (including the senses between my legs) I was cumming in no time with my ass clamping down hard around his cock.
Perry stated that he was going to take a quick shower, and let Jimmy and I shower after him (wish my shower were big enough for 3, but it was not). He would get beers out of the fridge and meet us in the living room. Jimmy and I came walking out with towels wrapped around us to find Perry lounging in my recliner with his towel unwrapped, sipping on a beer and trying to find some sports on my TV. Beers were waiting for us on the coffee table. Jimmy and I grabbed the beers and sat on the couch.
Jimmy said to me: “So Jack, you want to find women to have sex with? And you think that dating site is the way to go? You do know that it’s a lot easier to get a guy in the sack, than just about any woman.”
I smiled and just said: “As much fun as I am having with you guys, I just miss the touch of a woman. Because of my position in my company, I cannot hit on women that I work with without running the risk of being charged by my company with sexual harassment, regardless of whether the woman objected or not. The website is something that I’m trying. I’ve never been a fan of trying to pick up women at a bar, or in the grocery store. Some guys have that knack, but I’m not one of them. As far as getting a guy in the sack, I’ve thought about it, I’m just not sure how to do it. I’ve never attempted to pick up a guy and I don’t want to get punched for approaching the wrong guy.”
Jimmy said: “You know there are websites that are for guys. You can find dates there if that is what you’re looking for, but mostly they are for hooking up. There are a lot of flakes on there, but if you’re horny and needing a cock or an ass, a guy like you should be able to find some new friends.”
I smiled. After a session like we just had, I’m not sure that I could handle new friends.
Jimmy added: “Why don’t you think about it? Come over to my place tomorrow night and I can show you a couple of websites, and we can even set you up with a profile if you like.”
I held my beer bottle up to Jimmy and said, “Let’s do it.” We clinked bottles and set a date for tomorrow. After a few more moments of chatting, Perry and Jimmy were ready again. We headed back to the bedroom, and it was just more of the same, boring sex that I’ve experienced with them before, so I won’t bore you with the details.
I left work the following day at 6, ran home, showered, changed into something casual, and headed over to Jimmy’s. I arrived just as his brother, Matt, was about to leave. Jimmy introduced me to Matt. While I had been to Jimmy’s several times, this is the first time that I was meeting his brother. I told Matt that I hoped I wasn’t chasing him out, but he assured me that he was expected at a friend’s. Matt looked to be in his late 20s or early 30s, somewhat taller than Jimmy (about 5’10”), slender and handsome.
After Matt left, Jimmy grabbed a couple of beers and we sat at his kitchen table. He had his laptop set up, and a website open. Jimmy pointed out that the current screen showed all of the guys online in our city. There were 10 pages of guys. He said the website had just started asking for permission to obtain your location so that it could show you who was online near you. Jimmy moved the cursor to hover over a button that said “Near Me”. He clicked on the button, and a new set of pictures showed up on the screen. The first profile listed had a profile name of JMG1. Jimmy stated that was his profile, and a note on the profile stated that this profile was within 100ft of our location. The profile picture was of him laying on his stomach, on his couch, totally nude. The picture was taken from above his head, and as you looked down his body, you could see his hairless back and those marvelous, smooth buns. That picture and the memories of fucking that ass had me starting to harden.
He clicked on his profile and there were a few more pictures, including a picture of his groin and a shot of his face. There was no doubting that this was Jimmy. I asked him if he was not worried about these pictures being on the internet, including a face pic?
Jimmy stated that this website only allowed you to view profiles if you were a member, although it was a free website, so anyone setting up a profile, with or without pictures, descriptions, etc. could view your profile. And he stated, that while WE could see his face pic, it was not available to everyone, only those people he chose to share it with. He closed his profile and clicked on one that said it was 2 miles away. He pointed out that this guy had one profile picture of his chest only, and he had 3 private pictures. Jimmy stated that those private pictures could be unlocked for Jimmy by the profile owner, and may show face, cock, ass or his pet sheep.
Jimmy pointed out that the profile we were looking at listed the guy as a top, age 50, height of 6′ and weight of 195 pounds. He also listed his cock as being 8 inches. Jimmy turned to me and said, “do not believe ANY of what you read on the profiles. Some of the guys are entirely truthful, but some are just lying sacks of shit. This guy’s minimum age is 50. He may be 6 feet tall and his weight will be anywhere from 190 to 240 pounds. If he says 8 inches, count on it being 6 and be pleasantly surprised if he was not exaggerating. Finally, these pictures may be taken yesterday or 10 years ago. Know all these things before you decide to meet and be prepared to be disappointed.”
“Well, so far, except for the nudity, it’s no different from the dating site I signed up for to meet women.”
“Exactly, but remember that men taught women how to lie, so they are more experienced at it.” I looked at Jimmy and he was smirking. I never asked if he was serious.
Jimmy closed the profile we were looking at and opened another one with no picture showing. The name on this profile was “Thomas9.5″. In the description, the guy states that he is Black, 5’11”, 175 pounds, 45 years old and that he is a Top. It also stated that he practiced “Safe Sex Only”. There was no listing of dick size and there were no private pictures to request to be opened. In the statement section, the profile said “Total top. Prefer middle aged, white bottoms or versatile. Height/weight proportionate is important to me.”
Jimmy told me that this is Perry’s profile. My first thought and I said it out loud, “Perry is 45?”
Jimmy laughed and stated that no-one is sure of Perry’s age. Sometimes he says 40. Sometimes he says 50. In this case, 45 is close enough. If you were to meet him, you would know it was close enough.
I asked: “Why does his profile name say Thomas?”
Jimmy stated that Thomas is the name that Perry uses until he knows someone. He feels that the less known about him, the better. Also, Perry is still separated from his wife and he keeps a lot of information hidden for that reason. “Did you notice the 9.5 in his profile name? You do know what that is in reference to?”
It had not occurred to me until Jimmy asked, but when he brought it up, all I could think of is the black python that hangs between his legs. “I hadn’t thought of it until you said something, but yeah … I think I know what it refers to.”
Jimmy explained that Perry doesn’t list his cock size in his profile, but the 9.5 in profile name gives his potential partner an idea of what to expect and even though it might be a slight exaggeration, his bottom would not be disappointed in his size. I know that I wasn’t.
While we were discussing Perry’s profile, I heard a ringing sound come from Jimmy’s computer. Jimmy stated that we just got a message. Sure enough, along the top row of the page, at the heading that said “Mailbox” there was now a number 1 in a circle next to it.
Jimmy opened the Mailbox and said that it looks like the guy we were looking at prior to Perry was interested and has unlocked his private pictures. Jimmy clicked on the profile name and now all the pictures were shown. In addition to the chest picture from before, there was now a picture of a flaccid cock and another picture of a hard cock with a hairy, not quite flat belly above it and a nice set of balls below it. Finally, there was a face pic. It showed a guy with some grey hair, and a scruffy, salt and pepper beard.
Jimmy told me that this guy really doesn’t interest him and he just closed the profile. I asked him if he was going to send a note to the guy saying thanks, but no thanks. Jimmy stated that he does do that occasionally, but mostly he just ignores these things if he’s not interested. Hmmmm … again, a lot like the dating website that I was using for women. I had sent out many notes to women and received absolutely no response in return.
Now Jimmy showed me a button that said “Last Visits”. He clicked on it and a list of 10 profiles showed up. Jimmy stated that these were the last 10 profiles that had checked him out. Sure enough, number 2 on the list was the guy that had opened his private pictures to Jimmy. The most recent one was a profile that listed someone as 18 years old. Jimmy clicked on it and it had a couple of pictures of what looked to be a smooth ass and a smooth groin.
The profile description included: 18 years old, 5’5″, 120 pounds, 5 inch cock, bottom. Under the Sex Practice heading, there was nothing listed.
Jimmy said that what I do was entirely up to me, but he stays away from these profiles for several reasons. The biggest reason being that there was no way to verify that this person was indeed 18 years old. He warned me that I may enjoy a young ass, but if I were EVER caught with a guy that was under 18, regardless of whether he stated that he was 18, 19 or 42, I would be going to jail. My cock just deflated. He also noted the lack of response under the Sexual Practice heading. “A lot of these younger guys are reckless, and practice unsafe sex on a regular basis. That’s just not for me. As you know, I enjoy multiple sex partners, and I would never fuck or get fucked by anyone without a condom, at least without knowing them a lot better than what I just learn from reading their profiles.”
Jimmy asked me if I wanted to go ahead and set up a profile? I wasn’t entirely sure, but decided that I’d give it a try if he assured me that I could take it down if I changed my mind down the road.
After discussion, this is the profile that we came up with:
Profile name: pdiddyd55 (NOTE: this profile no longer exists. I had my reasons for choosing that name and I truthfully did not know of the rapper by that name at the time I chose it. I deleted that profile and chose a new name because of the confusion it was causing. Everyone expected me to be black and I received several comments about false advertising.)
Age: 52
Height: 5’10”
Weight: 185 pounds
Dick size: 6 inches
Sexual position: Versatile
Sexual practice: Safe Sex Only (Perry was the only one that I was not using a condom with, and while I was willing to play bare with Jimmy, I left that up to him. I trusted that he would not put me into a situation that would cause me to get sick, and he was very open about playing with several guys, sometimes as many as 4 or 5 in one week … oh to be young.)
In my profile description: Versatile guy here. As a top, I prefer to play with younger, smooth and slim (Jimmy explained to me that I was looking for twinks). As a bottom, I enjoy masculine men of any age. Being height and weight proportionate are far more important than age or experience.
Jimmy took a few pictures of me, cropping the face from all pics. I had no private pictures. One picture was similar to Jimmy’s with me laying on the couch, fully nude showing my back and ass. A second picture was of my cock and balls. Jimmy had worked me to full mast to show my full 6 inches. The last was a picture of me with only my boxer briefs on, sitting on his couch, with my legs crossed. The idea was that I was relaxing back. That became my profile picture.
With that completed, Jimmy and I headed for his bedroom. The profile would come into full use in the upcoming weeks.
Once I was in his bedroom, Jimmy had me lay face down on his bed, in the nude.
“Have you ever had a massage, Jack?”
I replied, “I’ve had a few.”
“I’ve toyed around with giving massages. Let me give you one.”
I turned my head to see if he put clothes on. He had not. “Go for it. Do I have to tip you at the end?”
“I’ll let you decide.”
Jimmy actually did a pretty good job, although I was not a connoisseur of massages. When I flipped over, of course I was hard. Jimmy crawled above my head, and started by massaging my face, then as he moved to my pecs, he draped his cock over my forehead. Once the pecs were done, the massage moved to my legs. When he got to my thighs, as he rubbed up, his thumbs would rub my balls.
“Ok, Jack. You get to decide how we finish.”
He lowered his mouth to my cock and caressed my balls. He gave me a couple of sucks. “Do you want a traditional happy ending?”
Then he shifted so that he was sitting on my groin, with my cock set in the crack of his ass. “Perhaps you’d like to fuck me?”
Finally, he moved around again, lifted my legs and put them on his shoulders and started fingering my ass. “Or, you could let me drill this ass of yours. What do you think?”
I thought about my options. “Can we start with a 69, then do a flip fuck?”
Jimmy smiled. “You want the deluxe package. Let me grab the lube and condoms.”
When we finished, Jimmy checked my profile which had been left up on his computer. I had a couple of messages. I decided to check those at home.