This is a true story that happen in 1971. I was 16 years old he was 52 years old. First some back ground. My dad died when I was 12. At 14 I started sucking my best friends (Jimmy) cock when ever he want it. That was around the same time I discovered cross dressing. My mom found a good paying job at a factory working second shift. I was home alone nights and would dress in her sexy things and masturbate. I was a shy plump small dick kid growing up. My dick was and is only 4 ins when hard. When soft luck if it's 1/2 ins. Plus to top it off my balls are tight and do not hang. I all so had man boobs that are even bigger now as I gotten older. ok the story.

My mom finely got a new man in her life and was away on vacation for 2 weeks. It was play time. I got to wear mom's things. She had lots of stockings and garter belts. I was enjoying wearing her garters and stockings jerking off. That buddy I been sucking since I was 14 gave me some very hard core magazines from his fathers stash. These were not like playboy but very hardcore with nothing but pics in them. Gave me 2 str8 ones one gay one. They showed everything and lots of cum shots.

So it was just getting dark out I was in the den wearing my mom's tan stockings with her red garter belt and her black bra. The cups on the bra were to big but I enjoyed the feeling. I got her big 10 in dildo in me slowly masturbating looking at the gay magazine. I nearly jumped out of my skin when I heard a knock on the window. To my horror there was my next door neighbor Henry looking right at me. I tried to cover up as I heard him say to late all ready seen you let me in. The curtain on the window was open just enough for him to see. I walked over to the door opened it a little and said what's up. He said let me in want to talk. I was so scared and nervous my hand was shaking. He walked in shut the door behind him looked me up and down smiled then walked over to the coffee table picked up the dildo looked at me smile then picked the magazine up looking at it said why aren't you a fag. He said how long you been doing this? I said first time he yelled don't lie to me. I told him then he seen my face and said don't worry it will be our little secret. I said really! he said yea. He looked between my legs and said you are small. I whispered I know. He was looking though the magazine he said this get you hard hun. I nodded my head yes. He handed me the magazine said here get your self hard as I watch. I said it might not be a good idea. He said if you want your secret to be safe it is.

He walked over to the window pulled the curtains closed so no one could see in then went over to the door locked it looked around making sure we were alone. He pulled the chair in front of the sofa and sat in it. He said well get it hard. I sat on the sofa started looking at the pics of gay sex. I asked him if he wanted to look at a str8 magazine. He said you have one! I got up and went to get one came back handed it to him and noticed he undid his pants and zipper. U could see his blue plaid boxers. I started stroking looking at the guy on guy sex. I was taking peeks at his crouch wondering what his cock looked like. I only played with Jimmy's cock but often jerked-off thinking about other cocks.

I was now hard as a rock he said you are small no wonder you dress like a girl. He was now rubbing his cock looking back and forth from my cock to the magazine. He asked me if I ever sucked cock. I didn't answer and he kept asked. Finely I said yes. He stared in my eyes as he pulled his cock out started stroking it. He said u like sucking. I nodded yes, He said did you swallow his cum, I nodded yes staring at his semi hard cock. He kicked his shoes off and asked if I let anyone fuck me, I said no. He seen I was staring at his cock.

He got up walked over to me stood right in front of me dropping his pants stepping out of them then dropping his boxers. Right in my face was my first look at a uncut cock. It was thick very veiny lots of hair with big I mean big hanging balls. I watched as he stroked it. I liked watching how the fore-skin slide over the head then back like a peek-a-boo show. The head was very pale and shinny. The shaft was darker in color and veiny. I looked up he smiled then grabbed the back of my head gently pulling my head to his cock. My hand replaced his and my mouth opened wide taking him in my mouth. My tongue danced all over and around the head tasting very salty. He was now fully hard and moaning. He said thats it suck it oh yea fuck your good. My head now bouncing up and down his shaft. My sucking became stronger and my tongue was licking harder. He said oh you cock sucker that feels so fucking good. I reach up with my other hand played with his nuts. He started shooting in my mouth. Globs of thick cum hitting my throat I was gaging. After he was done he pulled out. His cock was covered in cum. He grabbed his cock started rubbing all over my face said a good cock==sucker wear the cum to. He said did u like it, I said yes. He said want to suck me all the time I nodded yes he said good see you tomorrow ok I said yes and he dressed and left. I jerked-off a big load tasting his cum on my tongue.

I didn't sleep that night and jerked-off about 5 times. The next day just before he was to come over I showered and got dressed in my mom's black stockings with her black open bottom girdle that had attached garter straps. I wore her g-string black lace thong that barely covered my cock and balls. He asked where my mom kept her toys. I lead him to her bedroom and pointed to the night stand drawer. He looked in pulled all her vibrators and dildo's alone with lube. He started to get naked then got on the bed. He said come suck me hard. I got between his legs started to work his cock hard. He surprised me pushed me away the flipped me on my stomach started rubbing my ass. I was shocked more when he stuck his tongue in my ass. He got on top of me I felt the cold lube on my hole then his cock was at my opening. It hurt like hell going in he said relax let it go in don't fight it. He finely was balls deep and took my cherry that night. He shot a big load in me. It never did feel good that night. After about 5 times of him fucking me on other nights, It started feeling great. We did it for 4 plus years. His wife and my mom never found out or did anyone find out I was a cross dresser.