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I was lucky enough to get a job right away after college, it was one of the first things that put a smile on my face in years. I had gotten made fun of quite a bit at school for all the weight I had put on and was very embarrassed about my body. I was always a bit chubby all my life and when you added all the beer and pizza a college life provided a round ass and one great big set of man boobs now graced my body. It made me feel quite awkward at times but I did enjoy playing with them while I masturbated. I stopped going out in public and spent a lot of time at home or going to the gym to try to lose the weight.
It was at the gym where I met my soon to be boss. I always tried to go when no one was around because I was ashamed of my body, that was when I met Bill. He was this very large behemoth of a man who made me look tiny next to him. We began chatting away a bit and I found out he owned a sports store around the corner. I saw him staring at my body and giving me a big smile I was not sure what to think of it but he was super nice. We went in to change after working out and I was so comfortable around him now I did not try to hide my body like I had for years. I think we both stared at each others naked body equally, he had the biggest cock I had ever seen. I was not very hairy and when we were showering he came right out and told me that I was doing a good job at gym but it must be uncomfortable trying to jog with my chest. I turned quite red and hid them from him thinking he was picking on me. It was then I saw his cock growing a bit and I realized he may be into me. He told me to come over to his store with him that he may be able to find me something to help out.
I did not have any friends and really enjoyed talking to him so I quickly said yes. We walked over chatting the whole way and I swore I felt his hand graze mine on purpose while we traveled. He unlocked the back door of place and turned on the lights and it was very big and nice he had tons of clothing everywhere. Without skipping a beat he walked over to women's section and went to the sports bra rack. He had this domineering presence about him and when he told me to take my shirt off I never hesitated. It was simple it looked like a half a tank top and I pulled it right over my chest. I was in shock how comfy it was and lifted my chest up off my belly. He reached right out and started feeling them telling me it fit great and made me look much better and I could see him looking right down the front at the cleavage it had produced on my chest. I could not take my eyes off myself in the mirror my big nips were poking right through the material.
I looked over and saw him picking through the matching spandex bottoms next to the bras and came over and handed them to me. I held them up and they looked tiny like a bikini bottom. He told me it will hold me all in place and that he has guys buy them all the time. I really wanted to please him and have him be my friend so I pulled off my things and tried them on. My cock quickly shriveled up a bit in from the tight bottoms and he gave me a big smile when I turned and showed him how my things looked. He began rubbing his cock through his shorts and told me he would wear them if his cock was not so big.
I had fooled around with a couple guys in college on some drunken trips to the deserted men's room in the library, but had never wanted to really do much more. I felt myself submitting to this large mass of a man in front of me. He picked up my things off the floor and told me to follow him, in just the bra and shorts I went with him like a puppy. We got to the front of the store and he pulled out one of his stores t shirts from cabinet and told me to hold my arms up. I looked at his huge smile as I now had on a bright pink women's t shirt with his stores logo on it. I was in a bit of shock I was just willingly putting on girl's clothes in front of him but I also really liked the way I looked. He put his had on the small of my back and said let's get something to eat and led me to the back of store again and at the door to the street. He told me he lives right upstairs and that no one would see me. I went out the door and moved quickly to the stairs and as I ran up them I could feel my tits bouncing in unison as I climbed each step. It felt amazing to me I stood there cupping them not caring that he was watching me. I let out a huge smile and told him thank you that felt really good and just kept feeling how big they felt in the bra. When we got into his apartment he came right up close to me and told me he was glad he could help out. I was a large guy but looked so tiny standing next to him it made me feel very submissive to him. He gave me a quick tour of his place and poured us a couple drinks. He asked me tons of questions up where I was from and what college was like. I felt his hand keep brushing against my back and every now and then on my thigh. He made us some pasta and we sat back on couch chatting away and getting a good buzz from the cocktails. He asked me if I would be interested in coming to work for him and joked that I already had a cute uniform to wear. I just felt myself growing more and more infatuated with being near him and when his hand went to my thigh again I moved even closer to him.
We both turned at each other and he pulled me over onto his lap and we were face to face. His lips met mine and his tongue quickly shot into my mouth. I never had kissed a man but felt myself so attracted to Bill. His huge hands reached right up my shirt and began squeezing my big man boobs and pinching my nips like a woman's. I pulled off my shirt to give him better access to them and he started licking my nipples through the bra, he then pulled my bra down and popped each boob out so they were in his face. My arms wrapped around his head pulling him towards my chest driving me crazy as his tongue flicked each nipple. He then started talking dirty to me asking if I liked being his big sissy boy, I could do nothing but nod yes to him. I could feel the bulge in shorts rubbing against my crotch as he kept working on my nipples.
He pushed me to the side and stood up in front of me as I sat on couch. His shirt came off in one quick tug and he dropped his shorts right down and his huge cock sprung out in my face. The look of his naked body in front of me led me to know I wanted to do nothing but please him. He put his hand on the back of my head and led me to his cock and I obligingly opened my mouth for him. I could not get enough , I had given out a few bjs in secret before but they were nothing compared to this monster. As I caught my breath he began rubbing the head of his cock on my tits. He told me to squeeze the sides of my tits and that he wanted to tit fuck me like a good slut. I had never felt so compelled to do as someone told me until now, in the next second his saliva covered shaft was sliding in the valley between my tits. His cock head kept popping in and out of my mouth leaving me wanting more and more. After a few more strokes he put my head on his dick again and I felt it begin to explode into my mouth. I swallowed almost all but some dribbled out and onto my chest leaving me a sweaty mess. When he pulled away he said that I passed the interview with flying colors and that I should was off my uniform before I started on Saturday.