Age when it happend: 39
Where it happened: Hotel
Wanting to TRY gay. I posted an ad. Got tons of WERID replies. I was looking for a specific type of person, Older over weight, or younger twink type. This one caught my eye. and we emailed back and forth for a while then he suggested real time, with Video. we did this and again after a while we both got comfortable with each other, We would jack off for each other Fuck our selves with various objects. He got women’s clothing and wore them. telling me how GREAT they were to get ya VERY excited, and suggested I get some. I finely ordered some. I was too embarrassed to go to a store.
The day they arrived I was VERY excited I got online and showed off my bra and matching panties and I even got some stockings with a garter. The panties were the crotch less type to let my balls hang out.
Robert picked everything out for me online. I never thought about letting my balls hang. or wondering why I would want this…. That night I jacked off for him 4 times. and 2 times afterwards. This dressing as a woman was GREAT. He told me I needed some lipstick makeup to do my eyes and such. I got this at the local Walmart. I found myself racing home to get dressed and couldn’t wait to be seen in this get up. Robert started getting more demanding as time went on. He told me for tomorrow night I better have some water balloons for my tits. and to get brown to match my skin color. or there will be no jacking off…. I did as told…
after 4 weeks of dressing. he told me. it’s time. for us to meet in real. I was scared. all this playing I told him a few times I would suck that cock dry. and my a hole wanted his cock…. We both are drinkers so to calm my nerves we would get a hotel room. and get drunk and just talk. I agreed. He told me to bring my Woman’s clothing because he’s bringing his. we could maybe trade some panties and such…… Excited, Scared. Nervous, all of the above was me. after we got into the room I started drinking heavy. IT didn’t take long b4 I was drunk and talking all kinds of trash. Robert had brought some VERY DIRTY magazines. I was looking through them. and WOW. Robert asked if I wanted to get dressed because he was. I said yes. but I needed to shower 1st. Robert was Quite drunk too. and he started the name calling thing. I told him online that it was ok. he told me it’s his way of getting off.
While I was in the shower he came in and said. Move over Bitch. I need my cock washed. This was the 1st time I ever touched another cock. I just reached and grabbed it and pored bodywash on it as I washed it. IT started to get harder than it already was. He then told me to Be sure and wash that pussy. With a slight slap on the ass…. Right as he was steping out, he asked if I pissed in the shower, or do I get out and piss. I said NO I pissed in here. he said Thought so. he was half in and half out with one leg on the tub his cock sticking straight out and he started pissing on me. as he did he was laughing and saying I bet you love that don’t you Bitch….. he told me to turn around and get a good splashing. I rotated and let him piss all over me. towards the end he lifted his dick and pointed it upwards. it hit my chest area. and then that was all of it. he started cussing, saying he wanted to give me a good face splash. I finished showering, and herd him say from the other room Put your panties on make some Good tits. and paint those lips. Bitch, and I ‘ll let ya have a beer. I did all this in the rest room. as I came out Robert had these magazines all over the room opened to various pictures. saying these one’s are my favorite bitches. besides you! He said to come over here get my beer and bend over by the bed. I did as told and he had me spread my legs. then I felt him hitting my balls that were hanging out of my panties. He was lightly spanking them, and laughing saying all Bitches love this. I don’t know if it was the fact I was dressed. of being humiliated. or even being called a Bitch But my cock was hard as a rock. I guess I did like it…… Robert finished with a big spank across my ass. and said ok come on….. I didn’t know what that ment. but he was patting the side of the bed. So I sad down as he pulled my head towards his cock. I opened up and took it. I wanted ot go slow. and work my way down but he forced my head all the way down. I was surprised IT all fit. after he let go. I started sucking this thing for all I was worth. I moved around on the bed to get more comfortable, leaving my panty’ed ass sticking straight up in the air my balls were flopping with ever stroke I made….. Robert worked his finger up my panties and straight into my hole. it went in smoothly, I was guessing he lubed it up. He was working my hole as I worked his cock. and he started the name calling again. he called me a cock sucking whore. a cum eating cunt. a piss covered fuck toy, and everything you could think of……
My cock was so hard I thought it was going to explode I reached down grabbed it and started pulling. it took about 5 strokes and I spurted. Not just a little I spurted everywhere. All over myself, all the way up to my chin. about this time I noticed Roberts cock took on a different shape. it was like it turned to stone. and got fatter. He started to moan, as he was pushing my head down again and holding it there. he shot his wad and man o man…… the first part made me choke as he was still moaning and forcing my head down. it went straight down my throat. he released my head I pulled off and he started jacking, it shot more cum right at my face then more, then more. I remember thinking will this ever end…… He stopped jacking off, and was just laying there. not a sound. then he said. always kiss the cock that comes in your mouth. sissy!
I thought he was right. I have become a sissy…. I kissed his cock and said thank you. I was a cum covered mess. I went into the rest room and showered again. as I came out he was fast asleep. I jacked off one more time and got into bed…. My Clothes were cum covered so I was nude. But sometime during the night I was awaken with him getting my ass. I woke up and it was already in there. he was fucking me on the side. He noticed I was awake and told me to get on my knees. We did this slowly not to let his cock come out. he was now on top of me riding my ass like a dog. and I was taking it like a slut whore….. Getitng butt fucked was not as bad as I thougth. in fact. I liked it. I was now the one talking. saying Oh yes fuck that pussy. tear that pussy up. I even told him that pussy was his and he got pussy any time he wanted…. he fucked me for what seemed like 10 minutes. I jacked off and came 3 times while he was doing this. then he pulled out, said turn around. I met him half way. to get a mouth and face full again……. after he was done. he collapsed on the bed telling me to go wash up, he said he doesn’t like his cunts to be cum covered………
I learned a lot about myself that night. I enjoyed humiliation. and Loved prancing around in women’s clothing. I was unsure about being pissed on. But it was part of the humiliation. I learned my new friend Rober was Quite the pervert and I loved it. I guess I am a Cum Cunt.