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This story is another take on my story "Servicing the Service Manager".
I'll leave it to my readers to decide which version they like better.
I was 17, horny, mature and ambitious, that summer I got an internship at a nice company assisting in some event planning and employee appreciation events. I was a great asset I was told by manager, she was delighted to have someone with my energy and zeal to get things done. I had lots of girlfriends (friends who were girls) and they gave me good ideas to keep things fresh. I wasn't gay yet, hadn't focused on things too much. I took my sexual disinterest in women as a phase. I was busy I was enjoying my days. Physically I was weird. I had a pudgy body, bit of a gut, but the two things that made my body awkward were my big butt and the start of breasts that I developed. I was embarrassed but my flamboyant personality helped make up for it. But I did know that 80% of the men I spoke to or interacted with could not help but gawk at my physical assets.
One day I had to ship some things off to another site and I took the box down to the mailroom or service center as we called it. I was greeted by a new manager, he had silver grey hair (far better than John Slattery if that's possible), smooth dark skin (I later learned that he was part Italian and part Spanish) and a lovely smile. He stood at about 6'0, a towering frame over my 5'7. He was broad chested and muscular from spending a life of hard work. I was attracted to him, I caught myself flirting with him. Getting to business he asked me if the box was heavy and I said somewhat, he asked if I could put it on the scale as he had a bad old back. I couldn't help but say "old oh come now you're not an old guy, you must be in your thirties." He stared at me and smiled, I lifted the box up and found his hand on my left arm and heard him say "I'm not as young as you are." With that he got behind me to come to my right to get a closer look at the screen and he put his right hand on my right shoulder and his left hand moved from my left shoulder down to my hips and he stood tall behind me looking into the screen. I pushed my butt out slightly and grazed his crotch. He gave us space and moved back. Over the days I found excuses to seek him out, I acted submissive and asked him to lead and direct me. I struck up conversations with him and urged him to share personal pieces as well.
A few weeks into summer on a hot July day, I had helped organize a company picnic. I had ordered t-shirts for the volunteers, ice cream trucks and a whole bunch of activities. Riz showed up as well, he was dressed in dark blue jeans and a white shirt, I was impressed that he hadn't managed to get it dirty in the whole day of fun. There was a hiccup with one of the popular carnival games and I sought Riz out, he came to the rescue he rolled up his sleeves and in no time was it fixed. I went back to look and had fixed it. I went over to him and put my hand on his firm hands and said, "I owe you one for the game." I was intoxicated by the feel of his hard body. I gave him a big smile. As is the case with best laid plans, the sky turned dark and there was a huge downpour, I ran around trying to collect everything and got soaking wet. People began to disperse and the picnic ended early, a few volunteers stayed and Riz stayed to help as well. I went to the shaded area when everything was cleaned up, I was still wet to the core. Riz had stayed to help, I thanked him and noticed his gaze on my wet t-shirt, I pushed my chest out, and loved how the light yellow t-shirt when soaked had accentuated my large dark nipples and they were clearly visible. Was there a stir in Riz's pants. I hoped so.
Needless to say I caught a cold and didn't go to work the next two days. The following week I had to take the bus to work as my parents were going away to the cottage for the fortnight, and I would join them on the weekends. It was hot and public transit in the heat was not ideal, especially since I had to walk almost a mile from the stop to the office.
On the second day of my commute as I was walking up to the parking lot, a black convertible Mercedes drove by and someone honked, I looked and it was Riz, he waved and smiled. He parked his car and we walked in together. He commented on my taking transit, and I told him about my parents being out of town, he nodded and we went on our own ways. The next day I had quite a lot of work with the Service Center and interacted with Riz a lot, we even sat down to have lunch together, I learned that Riz was a widower, and loved to travel. I urged him to bring his pictures in, I told him how much I loved beaches. The following day I had a lot of work in the Service Center and to my delight when I probed Riz he brought up a stack of pictures. There were lots of pictures and I don't think he had flipped through them. I was surprised to find some of him in dark blue speedos, I was turned on to see his body. For a guy in his early 50s, he was in formidable shape. But what was worthy of mention was how well he filled the pouch of his Speedos. His package was absurdly large and unfit for the tiny speedo. I flicked through the pictures and lingered on each one of his in the bathing suit, he tried to rush me but I wouldn't, I asked questions about the location, people all to get to stare at him. I then came across a close up of him in the speedo and it seemed he was sporting a semi, he blushed and commented that he didn't know how that got in there, it turns out there were two copies. Luckily and employee came by with a letter and I quickly stole a copy and put it away and then returned the stack to Riz. I asked to see the pics often that day, and was disappointed when he didn't bring them in the next day.
The very next day was a Wednesday and I got off the bus and as I started walking and saw Riz coming down the road, I waved frantically and he saw me and stopped, I asked him for a lift and he welcomed me. I was nosy and asked him how we could afford the car, and he commented that he had run a successful business and retired early to spend time with his wife. He was working to stay busy after his wife's demise. I put my hand on his knee said how touching that was. We arrived at the office and spent another busy day. I did not have to see him all day but I pulled out his picture and looked at it. I needed to feel his body on mine, I had never done anything like this but I just had to. I went down to the Service Center an hour before closing and finished some work and asked Riz if he was leaving soon. He looked around and said yes. I complained about the heat and walk to the stop and Riz kindly offered me a ride. I was very chatty on the way keeping him engaged with compliments and stories, we passed the stop and I hoped he wouldn't realize and lucky for me he only realized when he was pulling into the underground parking of his condo building. I assured him that I would be fine going on my own from his building and as such he parked. We got out and walked to the elevator and I commented on how parched I was and looked for my water bottle, not finding it I sighed. The kind man that he was, he offered me a drink in his condo. I jumped and agreed and invited myself in.
Riz lived in a beautiful condo high rise building. He had the penthouse with key only access to his unit. It had gorgeous views of the city and of the lake. He was clearly proud of the unit and gave me a tour of his office, his living room, kitchen, the spare bedroom, and then the master bedroom which had the best view of all. As I stood there admiring the view, I couldn't help but comment on the height and the view. He was standing by the dresser at the foot of the bed, this was my time, it was now or never. I walked to him leaned in and kissed him, he didn't pull back, he didn't realize what had happened. I stroked his cock, and it reacted to the touch and grew. I was poorly endowed and had seen many men and boys in gyms and in movies but this guy was something. It felt natural to drop to my knees and get to his crotch level. I looked up and Riz simply looked at me. Emboldened I grabbed hold of the coiled tube of flesh and squeezed as it hardened to my touch. It felt thick, lie wrapping my fingers around a baseball bat, but meaty and warm. It felt right in a way that grabbing my own never did. This was what a man's cock should feel like.I undid his belt, unbottoned his pants, and pulled the zipper down with my teeth. He stood there in his distended white briefs, his monstrous bulge stretching every fiber of his underwear. He didn't say a thing as I pulled down his underwear and freed the beast, feeling it grow even larger without its cage to hold it back. It was the most beautiful cock I had ever seen, it was thick and it was long, the tapered top to the solid base joined by big cum filled balls, his pubic hair kept well trimmed. I moved forward and took him in my mouth, he responded immediately. I heard him moan and grunt, his cock sprang to life very quickly. He was now hard as steel. He instinctively put his hand at the back of my head and he gripped by head. We were entranced, I tilted my head up and slowly rubbed his cock across my closed lips, then along my cheek. I brought it back to my lips and kissed it, that made him harder. I laid a soft hesitant kiss on the top of his cock, I could tell it was too much for him. I glob of translucent pre-cum leaked from his now very hard penis, I licked it up and looked at him, he was in awe. He said "my wife didn't like to ...". "Suck your mighty cock?" I added. He nodded and I continued my ministrations on his cock, I tried to take as much of him as possible, he was hesitant and first and then he began bucking his hips and feeding me more of his gorgeous slab of meat. It was amazing, he got into a rhythm and pumped his cock a few times and I heard a guttural groan of "aannhhhh" and he exploded in my mouth, I was drenched in copious cum that I tried to swallow but some drooled down my chin, on my face and my hair. His body shuddered and he steadied himself with a hand against the dresser. I was blown away with the experience, this was my first blowjob but it felt so right here, on my knees in front of this sexy man.
Riz stepped out of his pants and took his shirt off, he stood stark naked.
His massive cock hadn't shrivelled away but was still semi hard. I noticed a spot of cum on my shirt and made a joke about Monika Lewinsky. He laughed nervous about his nudity, he offered to throw the shirt in the laundry and I obliged, taking it off right away. He saw my naked chest, and I could tell that he was having a hard time looking away. I thrust my chest out and his eyes grew wider, I turned away from him and peeled off my trouser, I bent forward and pulled my briefs down to expose my smooth ass.
I turned to look, Riz didn't look away but was fixated on my ass. I started getting an idea ... I was an anal virgin and this man seemed to be into me. Could I change my virginity situation? Riz broke out of the trance and offered me a clean robe. He took his shirt off and stepped into the shower. I had peeked into his shower it was huge, probably a 6 person shower. I saw him soap up his muscular, hard body, and was turned on. I decided to be bold, I took off my robe and entered the bathroom, he didn't see me, I walked to the shower and opened the glass door and stepped in, he felt my presence and turned to look at me, he paused and the continued to shower, he stood by my side as I turned on the other shower as though we were at a gym. Not satisfied I turned to look at him and began to soap my chest area, he turned and saw what I was doing, his cock stirred he continued to look. I asked him if he could help soap my back, and turned my back to him, he came closer and started to rub soap on the small of my back then up to my shoulders, he pulled me closer and my hands were around my chest, he put them down and slowly and very carefully he soaped my chest and my pecs and my nipples as he circled them and then cupped them up and squeezed them, then with his thumbs and forefingers he squeezed the nipples, he did this a couple of times and I felt him push his now hard cock into me. I stepped out of his embrace and began to soap my butt, soaping it slowly, I then reached back and held onto his now hard cock, and soaped it and moved closed to him and aligned my buttocks to his hardon, he stepped forward, and I pulled my ass cheeks apart, his cock rested between them and he gently slid his cock up and down my crack, it was an awesome feeling, he reached out to massage my nipples, and the third cup and squeeze, I could not hold it any longer and I erupted with an orgasm. I pushed away and he let go and washed up and left the shower. He dried himself and left. I followed him and went to his room, stood on a rug and dried myself, my back to him.
I felt him close to me. His mouth hung open as he dropped his hands to his side. A tent started forming in his tent, and then as though he was in a trance he said "I've never ... with a guy, I mean what happened is so confusing. You're a guy but your breasts and that ass, and then you put me in your mouth ...." and he trailed off. Next thing I knew, I felt his firm hand on the small of my back, firmly pushing me down over his bed.
"I want to ... " he said, as his towel dropped to the floor.
I gave up all control as the older man spat on his finger and started rubbing my hole. I glanced back at the big cock now fully engorged and gulped. Riz told me to relax, as I did I felt that he had added another finger with his spit. Riz was finger fucking my ass and I was humping him. And then it stopped, I felt Riz fall on me and say "take some deep breaths, and try your best to relax. This will hurt, you're very tight and I'm very big for you." Riz got on his knees, grabbed my waist and pulled me to my knees. Now, with my head on the bed and my ass in the air, I felt Riz's cock at my virgin hole as he started pushing. I cried out in pain. I involuntarily clinched my butt muscles, but Riz told me to relax. Soon I felt the head of his big thick cock push past the outer ring. I gasped and cried, it felt like his cock was splitting me into two.
In a bit, when it seemed I could mange the pain a little he pushed in a bit more. Then pulled back out and then back in a little deeper and faster. Then he unceremoniously thrust all the way in, he was balls deep in my ass and I screamed in pain. He grunted. Riz started a long slow fuck of my no longer virgin asshole. He started increasing the speed of his thrusts and pulling my hips to meet his thrusts. I winced in pain, waiting for it to be over. He pulled out leaving me empty. I was relieved. He said "roll over onto your back and I did that, he pulled my legs over his shoulders and in one giant stroke was even further inside me. Riz started pounding my ass and with one final thrust he exploded inside me, he grunted so deeply. His grunt and thrust drove me over the edge and I exploded all over his belly. He pulled out and fell to my side to catch my breath. He got up and went to clean himself and brought me a towel too. I cleaned up and when I returned from the bathroom my clothes were laid out on the bed and he was nowhere to be seen. I dressed and went out to the living room, he had dressed in pants and a shirt and had his car keys in his hand. He told me he would drop me home. I nodded. We didn't talk much in the car, but when we pulled up to my driveway I put my hand on his thigh and thanked him. He stuttered to say something but I moved my hand further up and stroked his bulge and told him how much I had enjoyed it and how much I hoped he would welcome the fun we had. He broke the silence and said "what we did is wrong, I am not ..." I looked at him and said "Gay?" He nodded. I told him I wasn't either, but there was something about that afternoon and it didn't make him gay if I sucked his cock and if he fucked me. He didn't say anything. I let myself out.
The next day at work was awkward for him. But on Friday as we left work he asked if I wanted to join him for a drink, I nodded and he said "I hope my condo is fine." I nodded and smiled, I put my hand on his thigh as we drove, he slid my hand further up and I felt his tube of flesh, it had started to harden ...