I was 15 and my entire world was crumbling down around me. I found comfort with my school counselor.
Jose and I would spend the entire summer vacation fooling around. We continued to make out and rub our naked bodies together until both of us would shoot cum all over our stomachs. Despite my best efforts, that was as far as Jose was willing to go. I was definitely interested in going further with it.
I started stroking his cock for him. He wouldn’t touch mine but I didn’t let it bother me. I just enjoyed stroking his.
The final weekend of summer came and both our birthdays were a week apart. I was turning 15 and Jose 13. We decided to have a sleepover again and I told him this time I had a surprise for him.
My mom left for her evening job and once again Jose and I were alone. We both knew we were going to fool around now.
“Take off your clothes, I’ll be right back.” I said as I left my room
When I returned, I cracked the door open just enough to see Jose on my bed gently stroking his erection but not enough that he could see me. As I opened the door, Jose’s eyes opened wide, jaw dropped and he sat up. Why? Because I was standing in the doorway wearing one of my mom’s sexy lingerie pieces, with black stockings and her high heels I jammed my feet into.
“Whoa! What are you doing?!” Jose asked
“I told you I had a surprise for you.” I answered shutting the door behind me
I slowly walked towards the bed and got on my knees. I grabbed Jose’s dick and began stroking it for him. He laid down and put his hands behind his head. I took a deep breath and then put his dick in my mouth. Jose once again sat up a bit but I didn’t stop. Before he could protest again, he fell back on the pillow and was enjoying it. I was as well! He came in my mouth which was a bit unsettling at first but at 13, he didn’t make very much semen. Plus, I had tasted my own cum a few times prior just to see what it was like.
Fast forward to the first week of school and apparently Jose had told his sister Melina about us and sure as shit, she told the entire school that I was gay.
For a solid month I was being constantly harassed by students both verbally and physically. I was already overweight and poor, now they all knew my secret. Denying it was pointless. There was only one way they could possibly have found out. Jose told Melina and she spread it like a wildfire.
Once the harassment had started to slow down I found myself still struggling. My grades dropped and I wasn’t interested in anything except going home and putting on my mom’s clothes. It was the only time I felt safe. It got to the point where I would wear a pair of my mom’s panties under my boxer shorts all the time. Even to school.
Eventually I got called into the school counselor’s office. His name was Mr. Roberts but he let kids call him by his first name Bruce. He was 47, had black hair with a bit of gray. Tall, in shape and had a thick black mustache. There was a comfort level I had with him as he was my school counselor since 6th grade and was aware of my dad leaving and my recent struggles.
I spoke with Mr. Roberts for about and hour and pretty much spilled my guts to him including all the gay/bisexual feelings I had. The only thing I left out was the part about wearing my mom’s clothes.
I would go and talk with him twice a week during school and then a third time after school on Fridays for about 10 minutes.
Of course the more he listened, the more comfortable I felt and the more comfortable I felt, the more everything began to make sense…
It was on a Friday afternoon. I had finished my last class of the day and went to Bruce’s office. There was one kid ahead of me but she didn’t stay more than 2 minutes. Bruce opened his door, said goodbye to her and gestured for me to come in. I sat down on a couch he had in his office and this time he sat next to me instead of his chair behind his desk. It should be stated at this point I was completely in love with him even though nothing had happened up to that point. Him sitting next to me this time made me incredibly nervous, awkward and excited.
As we began to talk all I could think about was how attractive he was. I was getting unbelievably aroused! I uncomfortably tried to hide my erection with my hands in my lap but he wasn’t an idiot.
He started by placing his hand on my thigh and gently rubbing with his thumb.
“What are you so nervous about?” He asked casually
“I don’t know…” I mumbled back
Bruce then scooted right up next to me where our legs were now touching. His hand moved from my leg to my shoulder and before I knew it, he was kissing me! Shocked at first I pulled away but then I realized what was happening and I started kissing him back. His mustache tickled my nose.
We kissed for a minute or so before his hand began to rub against my erection. I let out a little moan. Bruce stood up, turned on his radio he had on his desk to cover some of the noise we were already making and he quietly locked his door. I don’t think there was anyone outside in the office but he was just taking precautions.
As he approached the couch I sat on he unbuttoned his shirt and threw it in his desk. He had an incredibly sexy patch of black and gray chest hair with a trail all the way down to his cock which I could now see bulging from his khaki pants. He began to unbuckle his belt and pull his pants down. I sat up and inched forward to the edge of the couch. Bruce kicked his pants aside and stood up straight. His cock was pointed directly at me. It was gorgeous! A nice thick 7” cock!
I slowly grabbed the base of his shaft and licked the tip. A few more licks and then I put it in my mouth. His cock tasted amazing! It was so hard but his skin was so soft and smooth. I reached around and grabbed his ass with my free hand. It was toned and tight!
I began to taste his pre cum on my tongue. That’s when Bruce grabbed my hands and stood me up. He gently removed my clothes kissing me in various places as he went along. I ran my fingers through his chest hair feeling his toned pectoral muscles. I felt a bit uncomfortable as he was in such good shape and I was a chubby and out of shape.
As my fingers continued to run through his chest hair he began to grope my breasts. It was the first time I realized I had boobs. Bruce pinched my nipples a bit and eventually started licking and sucking on them. It was such a turn on!
Bruce sat on the edge of his couch and started sucking on my cock. It felt incredible! His warm mouth and lips wrapped around my throbbing dick! It only took a minute before I shot all my cum in his mouth! He stood up and kissed me immediately after swallowing. There was a tiny bit of my cum in his mustache but I didn’t care. I was completely under his spell. I was about to find out just how far under his I really was…
Bruce walked over to his desk and grabbed a bottle of lubricant. At the time seemed odd he had lube in his desk but I found out later that he planned this whole thing and brought it specifically for me.
As he walked back towards me all I could think about was his thick dick swinging back and forth as he walked across his office. Bruce wrapped his arms around me and kissed me a few more times. Then we sat down on the couch together where we kissed some more. He slowly maneuvered me into position where I was on my knees bent over the arm of the couch. He slowly slid his cock up and down between my ass cheeks a few times. I knew what was about to happen, and even if I wanted to stop it I couldn’t. I was under his spell. But the truth was, even though I was terrified of what was coming, I wanted it so bad!
As Bruce continued to slide his cock up and down between my cheeks, he squirted a healthy amount of lube all over himself. It was cold at first but heated up and tingled even. Really erotic to be honest…
Bruce could see how interested I was in what was going on behind me so he once again maneuvered me into position bent over the arm of the couch. I felt him inch his body closer to me and then press the head of his cock against my anus. With one hand he held my hips and the other the shaft of his cock.
“Nervous?” He asked
“Mhmm” I mumbled
“As it goes in, push out like you’re pooping and it’ll go in easier and less painful.” He explained
Then he pushed his cock inside my ass!
It hurt like hell at first but as I did what he told me to do, it did become easier and less painful.
Slowly Bruce began sliding his big man sized dick in and out of my fat teenage ass. It was only 30 seconds or so before I was much more relaxed and he was able to fuck me.
Bruce had his hands on my hips as he thrusted his manhood in and out of my virgin ass. I couldn’t believe what was happening! I turned my head a bit to get a glimpse of him fucking me. I wanted to see him fucking me! It was so hot! Beads of sweat began to drip down his forehead and chest. His chest hair glistening with sweat was sexy!
Bruce smacked my ass a few times then pulled his cock from my ass and demanded I rolled over. I did exactly as he wanted. I laid on my back and lifted my legs up. Bruce shoved his cock back inside my ass and resumed fucking me. I already felt like a pro at this.
Bruce was fucking me for over 10 minutes now! My legs lifted in the air and draped over his shoulders. Sweat dripping from his body onto mine! My hands running up and down his chest! Bruce slowed down and shoved his cock deeper and deeper for 5-10 thrusts then picked up the pace again. He was now fucking me harder and harder with every thrust. I was on the verge of tears I was moaning so loud. Bruce had to cover my mouth with his hand!
Then he quickly pulled his cock from my ass. My legs fell. Bruce grabbed his cock and unleashed a huge hot man sized load of cum all over me. The first shot landed on my chin and cheek. I opened my mouth hoping the next would find my tongue. The second landed on my chest and the third and fourth on my stomach. As Bruce groaned and squeezed out the last few spurts on cum and flicked them at me I swiped up the cum on my face and chest with my fingers and put it in my mouth. His cum tasted so much better than my own and a million times better than Jose’s.
As things calmed down in the room, Bruce tried to catch his breath and I laid there covered in sweat and cum, a confused 15 year old boy that just lost his virginity to a 47 year old man, I found myself quickly thinking about everything that lead up to this moment. Suddenly everything made sense to me…
I would wear my mom’s clothes and masturbate, fantasizing about being her. Just now realizing the resemblance Mr. Roberts had to my dad. I knew there was some kind of connection there but I was too exhausted to figure it out right there. I knew it had something to do with my mom and dad though…
