After I rinsed off and dried I followed him back to his bedroom. He was lying there and all I could think about was, “God his cock is beautiful.” I wanted it in my mouth, in my ass, anywhere I could get it, this was the first time a man had ever fucked me and I could not get enough of it. I returned to the bed and lay next to him; he rolled over to face me and brought his lips to mine. At first I wanted to pull away, even though I wanted his cock in my ass, this just didn’t seem right kissing a man as I would a woman. He pulled me closer and pushed his tongue into my mouth as he pressed his rigid cock against mine, in that instant everything seemed right. He placed his hands on my hips and pulled me tighter as our kiss lingered, pressing our cocks tightly together. I slipped my hand down to his hard cock even as he did the same; his cock was so warm and soft yet so firm. I began kissing his body as I moved down, pulling his small nipples into my mouth one at a time and sucked like a starving child. This caused his cock to jump in my hand so I continued moving across his chest from one nipple to the other. His nipples were like hard beans on his chest. As I moved lower his cock seemed to grow and throb in my hand, my lips trailed down until his raging hard cock was right in front of my mouth.
I opened my mouth and welcomed his hard cock; sucking on the head and running my tongue over it before taking it deeper into my mouth. He prompted me to move around so he could reach my inflamed cock and pulled it deep into his mouth. I forced his cock deeper into my mouth, unable to get enough of it, pushing the head of his pole to the back of my throat. Fighting to control my gag reflex I forced his cock into my throat just as he did the same. It was much easier to swallow his cock this time; for one thing I wanted to please Ted, which was my focus. I slowly fucked Ted’s cock in and out of my throat, now it moved easier; I could feel his balls against my nose. I removed his cock from my mouth and moved my lips along his cock to the base and on to his balls, trailing my tongue to his asshole. I pulled his cheeks apart and pushed my tongue as deep as I could; his cock throbbed against my neck. He too began working toward my asshole with his tongue, fucking my as with his stiffened tongue as I did the same to him. My cock was so rigid I thought it would break if he moved it and I could hardly breathe due to the excitement.
As I lay there, now pulling his cock back into my mouth, something was being pressed against my hot back hole; it didn’t really hurt, but I could feel the pressure in my asshole as the fake cock was pressed deeper. It’s well lubricated head slid into me with little resistance and was soon deep in my ass. It wasn’t as large as Ted’s cock but it was still a bit of a strain as it went deeper. I soon relaxed and he began working it in and out of my hot hole bringing me very close to orgasm. “Don’t cum yet, Jim, I am going to take you to a place few people get to go. Just relax and enjoy,” he whispered. He began moving the rubber pole faster and deeper into my hole, I wanted him to slam that thing as deep and hard as he could, every nerve in my body tingled as I lay there in an ecstasy unlike anything I had ever felt. I never wanted it to stop; I seemed to be floating just below a constant state of orgasmic joy.
He rolled me over face down and brought me to my knees. As I started to rise up on my hands he pushed my shoulders back down and told me to lie just like that. He wanted me to be passive but I wanted to get his cock in my ass right now. He removed the dildo from my asshole and began working lubricant in and around my asshole. This super slick lube would probably allow his head to slide it with only slight resistance but he used his cock instead. He pressed the head of his cock past the first muscular ring sending a pleasant bolt of pain through my ass, “Fuck me!” I begged. Once again he reminded me that this was going to be special, “Just relax, I will be in complete control,” he said as he inched deeper into my hole. I could feel my asshole being spread wide, dividing the walls so far apart I was certain they would split but didn’t care. He slowly fucked my ass and I wanted more, my cock was rock hard and wanted release so bad I feared it would split in two. I begged him to fuck me harder and faster but he just kept that maddeningly slow pace.
“This is going to hurt like pure hell, just relax as best you can, the pain and cramps will subside shortly,” he said as he pushed deeper. The head of his cock pressed against my prostate and the cramps began. It felt like I was about to climax every time he bounced against it, then he went still deeper. I couldn’t hold back the loud groan of pain as he pressed on; suddenly it felt like something gave way and his cock was buried to the hilt in my ass. The pain was like fire and the cramps and were so bad I thought I would black out…then he began moving. The cum that was dripping from my cock became a flow and every time he pushed deep into my asshole that flood came again and again. The pain had not let up much but the pleasure had increased beyond belief; I was in a constant state of orgasmic bliss and I had yet to touch my cock. He moved his cock almost all the way out then back in slowly, all the way. Then he began to speed up, he began fucking me like a mad man, driving his cock as deep and as hard as he could. He grabbed my rigid cock and began jacking it in time to his plunges into my depths. Shortly he began moaning and groaning like a man gone mad and grabbed my hips with both hands and began slamming deep into my ass then released a torrent of cum into my stretched asshole. I grabbed my own cock and beat it like a crazy man and climaxed harder than ever then passed out on his bed, his cock still in my ass.
I don’t know how long I lay there but at some point I got up and took a shower. When I cam out Ted was still asleep so I got dressed and slipped out the door, to my car and headed for home. My apartment actually belonged to a friend who was over seas for a year so I was helping him out while he helped me. Once in the apartment I poured three fingers of single malt and dropped into a chair. My guts still ached a bit from the deep fucking I had just enjoyed and my lower back ached as well but another scotch and the pain began to subside. I began thinking about the last twenty-four hours and, maybe not too surprisingly, my cock began to rise. One of the greatest jobs I have ever had was as a bouncer at one of the local topless bars in town, I had the pleasure of meeting a lot of people and most of them were female. One of those was a sexy number named Jesse; she and I had gone out a few times and enjoyed jumping into bed from time to time. I called her and asked if I could come over, she agreed even though it was late.
Jesse lived in the same complex so I only had to walk a couple of hundred feet to get to her place. When I arrived she was dressed in her usual “at home” attire, damn near nothing. She poured me a scotch and we sat down and talked. I told her the whole story, front to back including the fact that I did enjoy it and was now a bit confused by that fact. As we talked her beautiful green eyes became dreamy and she kept getting closer, “Jim, I have a friend who is bi and married to a man who is bi. I have wanted to hook up with her for some time but hubby won’t allow it unless I show up with a partner for him. I took Shelly over one day but she took one look at his cock and ran for the door when he mentioned he really preferred anal. Why don’t I give them a call?” I was astonished, “Jesse, I came over here to think through this thing, not to find another hook-up. Besides, my asshole is a little too tender to have it attacked again right now.” “Look, Jim, let me call them and we can set it up for Thursday night, that will give you time to heal and we are both off that night. If you change your mind between now and then we can call it off,” she begged. I stood up and stormed from the room, “I come her to talk and you want to get me fucked just so you can be with some other cunt. Fuck you.” I stomped out of the apartment and back to mine, steaming so badly I couldn’t sleep without another double.
The next day Jesse stopped by as I was cleaning up the Harley in preparation for a ride on Sunday. “Jim, I guess I am not much of a friend. You were right, I should have taken time to listen in stead of considering my own agenda,” she said. I really wanted to blast her, to let her know she really was a piece of work, but I had been doing my own thinking. “Look, Jesse, maybe I jumped a little too quickly, I will see you after work and we will talk,” I said. She smiled, like I had just given her what she wanted to start with and drove off.
Work that night was a real bitch; every drunk in town must have stumbled in and couldn’t keep their hands off the girls. I eventually had to break bad on one of the drunks and I beaned him with a sap and called the cops. Jesse and I headed out to the local coffee house to talk. “Look, Jim, why are you so worried about being gay, or bi or whatever. Your wife is out of your hair now and moved to California, your day job has just about put you over the top and you will be able to quit this crappy place before long. Everything is going your way and you have just discovered another side of yourself, you really need to chill and just go with it. If you discover it’s not your cup of tea, then blow it off, it’s not like you are going to marry some guy because his cock feels good in your ass,” her voice getting a little loud and people looked at us strangely, I indicated for her to keep it down a bit. “That’s not it, Jesse, I have always thought being queer was way off the charts, particularly for me. Now, here I am making it with a guy and find myself enjoying having his cock in my mouth and ass. It just doesn’t sit right.” She held my hand as she looked at me, “Jim, drop the labels for a minute here and look at it as enjoying another side of sex you had not explored before. Just think of it as sex, not whether it is with a man or a woman, just sex.”
A part of my mind could wrap around what she was saying but another part was screaming at me to get straight. I sat there thinking about what Jesse had said, about the time I had spent with Ted and how much I had actually enjoyed it and thought about doing it again and my cock jumped. “Jesse, if I agree to meet with your friends there are two things they and you need to understand; first, no one can ever know about this, it could really fuck me up; second is that if I decide I can’t go through with it then everything stops,” I looked into her green eyes. She sat there a minute, “The first part is no big deal, but if you suddenly decide it’s a no-go while Steve has half his cock up your ass I don’t think he will stop,” we both laughed. I sat there drinking cold coffee, “Ok, make the date. I just want you to know I am more than a little uncomfortable with this thing.” She looked at me and smiled so big I thought her face would split, “You won’t be sorry, I just know you are going to like Steve and Lana.”
When Thursday came I was a nervous wreck; my stomach was doing flips, my asshole tingled, my cock would not stay still and the temperature seemed to be going from hot to cold and back again. I knew I didn’t want to get drunk but about thirty minutes before Jesse knocked on the door I knocked down a double scotch followed by another. Jesse looked amazing, now I remembered why I was always happy when she was in a “fuck me” mood. Jesse is tall anyway, 5’7” or so and the heels she was wearing took her close to my six foot height. He long dark brown hair shined in the light and her green eyes seemed to gleam. She was wearing a white dress that fit her like a glove, showing off her beautiful breasts and her gorgeous body, I stared at her, “Tell you what, why don’t we skip them and go tear up my bedroom.” She smiled, “We can do that tomorrow night, right now I want to feel Lana’s tongue on my cunt while I watch Steve fuck you silly. Come on, let’s go.” I knew her comment was meant to lighten me up but that picture was stuck in my head, then I remembered something she had said about Shelly, “Jesse, you said Shelly ran out the door when she saw Steve’s dick…how big is he?” She looked at me thoughtfully, “I should have told you before, he is hung like a horse, but you should be able to handle it.” I could feel the color drain from my face and I began sweating again.
I felt like the fatted calf being led to the sacrificial alter as we approached the door. When Lana opened the door I almost dropped my teeth; Lana was a girl I had met at a party about six months ago, well, I can’t say I really met her I was third in line to bang her and there were more behind me. Lana was a real knockout though; her shiny hair was dark brown and flowed halfway down her back and gave her an almost ominous appearance against her brown skin; her eyes were as dark as her hair and lips so full I wanted to push my tongue between them. Her breasts were a little large for my liking but were beautiful none the less but seemed overly large compared to her slim waist and narrow hips. I could only imagine what her ass looked like, I was certain it would be perfectly shaped. She was wearing a light green dress that hugged her body perfectly, looking like it was made to fit only her. Jesse hugged her tightly then introduced us. Lana looked at me, “I remember you, you were the one at the party who fingered my asshole when you were fucking me at Carla’s party, you were the first one to make me cum,” then she wrapped her arms around me and kissed me like an old friend, then pushed her tongue teasingly into my mouth.
“Hey Lana, I thought you were with Jesse tonight,” came a deep but soft man’s voice. She broke the kiss, looped her arm in mine and said, “Just testing for future reference,” smiling. Steve met us half way and offered his huge hand, “Hi, Jim, I have heard a bit about you from Jesse, come on in and have a drink,” he said as he gripped my hand firmly, pulling me from Lana’s arm. Steve was not what I would have considered your quintessential homosexual, there was nothing feminine about him. He was tall, well over my six feet and build like a fighter; he had broad shoulders, a thick chest and a narrow waist; trying not to be obvious my eyes drifted toward his crotch but his loose fitting trousers gave little hint as to what was hidden within them This huge man seemed familiar to me, and I knew it was not from the party. We went into the den, which was much like the one in the apartment I lived in but decorated much nicer, and sat in the four chairs around the coffee table. Soon the discussion divided; Lana and Jesse were locked in their own discussion and Steve and I in ours. I soon discovered why he seemed familiar, he was a member of the Blue Diamonds Motorcycle Club; this was a club made up of active and retired police officers. We had been on a ride together last spring when we went to Daytona Beach.
As the ladies got up and left the room Steve sat back in his chair and looked at me, “Jim, Jesse told me you recently had your first experience with a man.” A lump formed in my throat that almost stopped words from coming out, “Yes. Steve, I hope you understand, I found that I enjoyed my evening with Ted but I am still a bit unsure, I mean I was raised that this is not right, but still I enjoyed it. A part of me wants to run for the door and a part of me is so excited I can hardly breathe,” I responded. He sat there for a minute, “I do understand and I will do everything possible to help you feel more comfortable and if you want to leave at any time I can deal with that…at least up to a point.” There was a tender firmness in his voice that let me know that once he was ready to push his cock in my asshole, it was too late. He reached into a bowl on the table and removed two fat joints, “This will help you relax and get your mind off the negative aspects.” We fired up the joints and acrid smoke soon filled the room and my lungs and soon went right to my head. About the third hit on the joint I started laughing; he looked at me quizzically, “It’s good stuff but not that good, what’s up?” I looked at him and managed to get myself under control, “Here I am, sitting down with a cop, toking up, about to get my ass ripped.” He began laughing as well, when he stopped he looked at me, “Are you feeling a little better?” I reached over and pressed my hand against his cock, “Yes, much better…now, where do we go from here?” He stood up and looked at me, “How about the bedroom?” We finished the weed, my head now so light I wasn’t sure I could walk and headed for the other side of the apartment.
The bedroom was, once again, much like the master bedroom in my apartment except that a king sized bed was centered against the far wall. As I stood there I thought, “So this is how a virgin feels on her wedding night.” Steve lowered the lights and began undressing, clumsily I did the same, trying my best not to look toward his crotch. When we were completely naked he pulled me to him and lowered his lips to mine, pushing his tongue into my mouth. As he pulled me closer I could feel his cock pressing against my body…yes, it was huge! my heart began to thump in my chest. Somehow we ended up on the bed, his lips moving down my body to my still tender nipples and began teasing and sucking them. My cock rose to the occasion and I could feel my whole body responding to his touch. His hand drifted down to my groin and he began caressing my hardening cock, then allowed his hand to slide across my balls and tease my asshole. His lips moved to the head of my now hard cock and slipped about half way down; it felt like wet velvet was wrapped around my rigid member. I was now so deep into euphoria that no concerns even entered my mind; either the pot had done it’s job or I liked men more than I thought.
Feeling like I should be doing something besides enjoying this I moved around until we were in a 69 position. Now I could see his cock more clearly…it was huge! I could just get my hand around it and it was easily nine or ten inches long topped with a large mushroom head. As I jacked his cock he pulled my into his throat easily and began sucking deeply as he applied more pressure to my tender asshole. My excitement grew and I discovered I wanted his finger in my asshole, I wanted his cock in my mouth and I wanted him to fuck my ass. Opening my mouth as wide as possible I managed to get the head of his cock in my mouth, fighting hard to keep my teeth away from his tender organ. I felt and heard him groan as I pulled as much of his cock into my mouth as possible; in response he popped his finger into my asshole. A wave of pleasant pain coursed through my ass and I could feel my cock jump in response.
He pushed deeper then removed his finger from my as only to return it coated with cool lubricant and easily slipped his finger into me. I tried to concentrate on sucking his cock as his finger slid deep into me and then back out over and over. Soon he added a second finger and my ass was on fire burned painfully in my asshole; I didn’t want him to stop. He continued to fuck his fingers in and out of my hole causing my cock to get harder still, so hard it was almost painful, but the pleasure covered the pain. I begged him to stop sucking my cock in fear I would explode and not want to continue; he removed his mouth from my cock and rolled me onto my back as he continued to tear into my asshole with his fingers. At that moment I wanted his cock in my asshole more than anything I could think of; the fact it was going to hurt just seemed to drive my passion higher. Somewhere in another room I could hear female voices as they were in the throes of their own passion. Steve removed his fingers only to return them with more lubricant then asked, “Are you ready?” I could hardly speak but I managed to convey my desire to him..
His body moved back up over mine and once again our lips came together in a deep kiss as he lifted my legs slightly and positioned himself at my rear opening. The mushroom head of his cock pressed against my asshole and he pressed forward. The lubricant was so slick that there was little resistance and he popped into my asshole with little effort. It may have gone in easily but the pain was there none the less. It didn’t hurt as bad as the first time with Ted but it still hurt like hell. His cock spread me further than Ted’s cock did but the pain was slowly subsiding and he began pushing deeper into my asshole. He slipped his hands under my ass and pulled me closer as he began fucking me slowly, the pleasure that was riding on the pain was amazing. He began moving in and out of me, slowly at first then increasing his speed and inching a little deeper with each stroke. The head of his cock hit something deep inside me and the pleasure increased to a degree that had my head spinning; my whole body felt like I was climaxing and I began to shake.
He was getting very excited now and didn’t seem to be in control as much as before. He grabbed my ass harder, bruising me with his grip as pulled me against him hard. My stomach cramped like crazy but the pleasure was so great I didn’t care. He was buried to the hilt and began slamming into me hard and fast. Faster and faster he fucked me, fucking so deep and so hard that he almost knocked the wind out of me with each stroke. The pain was still there but pain had taken on a different face, it felt good. He began groaning and mumbling, “God damn your asshole feels good, I am going to blow my nuts all up inside you.” My cock was spurting a constant flow of cum and my whole body was shaking, I was as out of control as he was. The pain, I loved the pain, it seemed the more it hurt the better it felt, “Fuck me, make it hurt, I want it to hurt,” I screamed. He pounded my ass with all the energy he had then pulled me tightly against him, he bellowed like a bull and unleashed his cum in my wanting asshole. He flopped on the bed beside me.
When he flopped to the bed I could now see Jesse and Lana standing at the door, naked Jesse holding a video camera in her hand. “My god, Jim, I have never seen anything like that,” Jesse said and the women left the room. I lay there, completely exhausted, fucked beyond belief and my cock still hard. Steve got up, straddled my hips and dropped his ass on my cock. It took only a few seconds before I released a torrent of cum into his asshole and we both dropped back onto the bed.