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 1
st
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 Karen and I met at the restaurant, and I found one of the pitfalls of online dating (outdated pictures).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.
