Apt 310
How could I ever forget?
It was the beginning of the summer of 1999. I had just turn 18. I was living with my parents in a 3 bedroom apartment in the city in Canada I will not name for privacy purposes. I was looking at my options in college and working a summer job. I began taking on responsibilities in the household, and decided to start doing my own chores. I started with laundry. Every week on a Thursday night I would go down to the laundry room and do my laundry. It was normally quiet and not busy. I would kick up my feet, read a magazine, or listen to some tunes on my discman.
It was one night while doing my laundry that I was alone, when I met him for the first time. He walked in wearing a tank top and short athletic shorts. I didn't say anything and minded my own business while he put his clothes in the washer. It was then that he asked if I had a loonie on myself as he had run out of change for the washer. In luck I had one for him, and handed it over. He thanked me, and began conversing with myself about how it's not cheap to do laundry these days. It was the first time I spoke with Bill. He was middle-aged probably in his mid-40's. He was amazingly fit for his age, and athletic muscular build. If I could compare him to anybody, he just about looked almost like the gay porn star, Chad Douglas, right down to the bushy mustache and curly hair, minus the tattoo.
We parted ways that night after the small talk, but would again meet up the following Thursday evening. He got to talking to me more and mentioned that he was new to the building and had moved in two weeks ago. We talked about the area around the building, and what was there to do. I had mentioned about several bike paths around the area and we both realized we were mountain biking enthusiasts. The talk was always small but never amounted to much.
We'd meet downstairs on a weekly basis. We would again talk about things of interest, and how our days were. I got to know him more, finding out that he worked as a carpenter during the day, and that he owned his own private gym where he taught tae-kwon-do and trained people. It was one night, that we were talking that he had offered an invite to come up to his apartment for a beer after I finished my laundry. I had declined the offer, feeling a bit awkward by the invite. I told him that I'd take a rain check. The awkwardness I had perceived as wondering if he liked me. I admit that I wasn't bad looking either. I was mixed with Portuguese / Spanish from my mom's side, and inherited a nice caramel tan. I kept my boyish looks, and kept myself fit with working out at the gym and mountain biking. I had been with girls before, but the curiosity of being with a man was intriguing.
I would meet up with Bill again in our laundry room. We would again get to chatting and we talked about what we did to keep in shape. Bill mentioned about offering a few free training sessions if I had wanted. I thanked him and said I'd take him up on it. It was that night that I started to think about if he actually was attracted to me. I fantasized that night in the shower, and found myself aroused by the thought of him and what he might do with me. Late that night, I found myself looking at gay porn and what Bill might be looking for or into. Considering I was the younger of the parties, I thought of myself as his twink, and looked at ways that might peek his interest further in me. I decided to test the theory. Over the weekend, I shaved my legs, and shaved my pubic hair off, keeping my body smooth. My parents questioned me one day because of my shaved legs, but I had mentioned that the guys in the gym were doing it as a look now and that it might attract the girls. I decided on my laundry night that I would wear something to show off my look. I wore short athletic shorts and a nice white t-shirt. I would meet up with Bill again as usual on our laundry night. We got to chatting, and he commented on my legs saying that they toned really well. I had thanked him, and passed a flirting remark about his calves and how muscular they were. I remember that night well, because I could swear that when I was bending our to put my clothes in the dryer, that I had caught Bill in the corner of my eye staring at my butt. We would again part ways and when I had my shower that night, I found myself jerking off to Bill and what he wanted to do with me and what I wanted to do with him.
I was hesitant to begin something with Bill, in my fear of somebody finding out, but I wanted to push it further to see if he was interested. It was the Thursday night ritual, and I met up with Bill again in the laundry room. We talked about how we were doing to keep fit, and mountain biking. I suggested that I show him some of the trails around the area. He replied eagerly, taking me up on the offer and we agreed that we'd meet up on Sunday for a mountain bike ride. I met Bill down at his apartment. I lived on the fifth floor, and Bill lived on the third. I knocked on Apt 310 and Bill had his bike ready. We both were dressed in bike gear, wearing tight riding pants. I had to keep my cool, as seeing Bill in the shorts and the outline of his package got me aroused. We took off from the apartment and took to the trails in a nearby park. We were a good 10 minutes into the trails when my bike hit a protruding root, and I wiped out. Bill stopped and asked if I was all right. I noticed my knee was a bit banged up, and Bill went into nurse mode. He got a bandage and gauze out of his fanny pack, and went to work. I sat on the side of the trail, and let him work on me. He poured water on the wound, and put the bandage on me. He kept asking if I was alright, and I shook my head. It was then, that he began massaging my leg and thigh. He massaged my knee joint. I leaned back , closing my eyes. He kept asking if i was okay, and I said yes. I rested for a bit, before we commenced again on our ride. We would finish up the trail and head back. I thanked him again for the treatment, and he smiled and said no problem. We would part ways. That night, I laid in my bed, just thinking about Bill. His touch and massage was exquisite. I decided that I would overcome my fear and make my move.
The night before our Thursday night ritual, I made sure to groom myself up, even going to the length of shaving my butthole to keep everything clean. I decided to wear my short athletic shorts again, and my white t-shirt. Bill would stroll into the laundry room as per his usual time. He wore his usual tank top and athletic shorts. He asked me how I was doing, and if I recovered from my spill. I said I was still recovering. It was then that I said that I was going to cash in my rain check for that drink. It seemed to surprise him, but he happily accepted. We talked while we finished up our laundry and I we went up in the elevator together. We got to his apartment and he let me in. It was a cozy one bedroom apartment. He kept it simple with a couch, armchair, coffee table, and tv in the living room. His kitchen was smaller than the apartment I was living in. He had some paintings of some motorcycles, and a painting of the statue of David on his walls. He handed me a beer from his fridge, and we said cheers. I walked around in the living room, looking at his paintings. I commented on his interest of motorbikes, and he mentioned that he used to have one but had to sell it prior to moving here. He sat on the couch, and I decided to make a move and sat on the couch beside just in arm's length away. He kicked his feet on the coffee table and I reciprocated. I made a wince as I put the leg that I banged up on the table. Bill noticed this and asked if it was still sore and offered to massage it. I smiled and said I didn't mind. He began to massage my leg, massaging my calf and working his up to my knee. I sat back on the couch, closing my eyes enjoying the massage and his touch. His hands worked his way up to my thigh, massaging it. I felt myself getting semi-hard, and tried to control myself to not let on this to him. However, I got goosebumps doing so, which might have led Bill to his next move. As he finished the massage, I opened my eyes, seeing Bill staring at me grinning. He put his hand on my back, rubbing my back and massaged my shoulders a bit. He kept grinning. I said nothing, and began to have butterflies. He kept rubbing my back, and it was then that he leaned forward and kissed me. It was an awkward kiss as I didn't know how to reciprocate. He apologized, but I told him that it was okay and that I had never been kissed by another man before. He then asked me if I had been any guy before and I told him no. He told me that if I didn't feel comfortable that I could leave but I assured him it was okay. I touched his hand, rubbing it to assure him it was okay. I then asked we could try the kiss again. Bill gave the okay. I leaned forward and cupped his face and began to kiss him slowly. The kiss was a slow passionate kiss, and I felt his tongue touch mine. He rubbed his hands on my inner thigh, and I became hard. It was soon that his hands moved to my package, and he rubbed it through my shorts. He asked me if I was a virgin to this, and I said I was. He asked if we could go to the bedroom. I said yes. He led me to the bedroom. I was about to have sex with a man for the first time.
Bill led me to his bedroom and he closed the door behind. We embraced each other, and began to kiss each other with slow passionate kissing. Bill's hands moved under my shirt, and he rubbed my back. He would eventually take my shirt off, and began to kiss my nipples. I remember his mustache tickling my nipples, sending goosebumps. I would eventually take off his tank top, and it revealed a somewhat hairy chest, with bright pink nipples protruding from the wires of hair behind it. I reciprocated and kissed his nipples as well, giving a little nibble to them. His hands moved to my butt, cupping it. He would eventually remove my shorts, leaving my tight Jockey underwear on. Bill then removed his shorts, revealing some tight boxer-briefs. We embraced again, and this time our kissing became more passionate. Our tongues played with each and we rubbed are hard packages against each other. His hands cupped my ass and I decided to push the envelope on my end. I began to kiss his neck, down to nipples, and worked my way to this treasure trail. I got on my knees and slowly pulled Bill's briefs off. It revealed an erect and wide cock. I would think it was a good six inches possibly. He had big testicles and had a nice trimmed mound of hair behind it. I took his cock in my hand and stroked it looking at him. He gave me a passionate smile, and a look to assure me it was okay and to go ahead. I had never sucked a cock before. I took a breath and began to lick his shaft up to the head of the cock. I kept doing this and then began to tongue around his head. It was almost like I was teasing him. I could hear Bill let out some quiet moans. I would eventually put both of my lips around his cock and began to suck him. He cupped my head his hands, guiding me. I sucked at a nice pace for him, and I put my hand on butt. I listened to him as he moaned silently, and at one point, I looked up and saw him with his eyes closed and his head leaned back.
I would eventually stop and got up back to kiss him again. Bill slipped my Jockey's off, revealing my cock. Our bodies embraced again, and we moved to the bed. He laid me down, and got on top of me. Our cocks rubbed against each as we kissed and our bodies pressed up against each other. I felt myself getting extremely aroused. Bill then made his way down to kissing my nipples, and eventually made his way to my treasure trail. He would work his way down to my cock, and began to kiss and caress it. It wasn't long before he began to suck my cock. He cradled my balls while doing this, and his mustache tickled it with every suck. I moaned in pleasure. He then worked his way down further and cocked up my legs in the air, exposing my butt. He pushed my legs up to expose my butthole, and began to lick between my balls and butthole. Eventually he pried my cheeks apart, exposing my hole, and began to tongue it. It sent waves throughout my body, and I moaned in pleasure from the rim job I was receiving. His saliva lubed it up enough that he began to finger me slowly while tonguing my taint. It was amazing.
Eventually he stopped, coming back up to kiss me again. Bill asked if he could have sex with me. I was worried about his girth, and admitted that I was scared it would hurt. He assured me he'd be gentle and that he was clean. I was hesitant, but I nodded in assurance. I felt that I could trust him. Bill reached into a night table and pulled out some Vaseline. He lubed up my butthole, slipping a finger into my hole and lubing the inside. He would rub it on his cock, and Bill held my legs up. I felt the head of his cock tease my butthole. He rubbed it against it and it slowly slid into my hole. I gasped a bit, taking a big breath in. Eventually his shaft slid in further, and he slowly pumped me. My hands gripped the sheets. It hurt somewhat, but as he continued on, the pain subsided, and pleasure took control. Bill got into a rhythm that suited both of us. My cock was throbbing, and I wanted to stroke it. However, there was no need to. As Bill slid as much as he could get in, I felt my cock throbbing out of control. I orgasmed and came on my stomach. I moaned and breathed heavily. Bill pulled out and laid on me. He didn't care that my cum was smeared on his stomach. He kissed me. He then said silently to me that he wanted me to cum again. I didn't think I could again but he assured that he would get me there again. I did feel kind of bad considering he didn't orgasm himself.
He turned me over to doggystyle position. My hole was gaping and ready for him again. He slid into again, and began to pump me. He worked his way back to the rhythm before, and I then felt his hand reach around and begin to stroke my cock. Bill wasn't wrong. My soft cock eventually became hard again. He eventually gripped my hips and I began to stroke my cock myself. My other hand gripped the sheets and I moaned in pleasure. I heard Bill begin to moan as well and his breathing became deeper. I knew he was close. I told him that I was close to cumming as well, but didn't want to get his sheets dirty below. He assured me it was okay. Eventually after two more deeps thrust, Bill pulled out and came all over my lower back. He let out a heavy moan. I would eventually cum as well from my stroking, spraying on the sheets below. I collapsed and Bill collapsed on top of my back. We eventually spooned together, and laid there for a bit to rest, letting the sweat cool our bodies. We laid there for about 15 minutes, before I said I had to go back upstairs. We dressed and he led me to the door. We embraced again with a hug, and I wished him a goodnight. I finally broke the ice with Bill and it would eventually lead to a couple more encounters that I will share with you on my next story.