Young Crossdress, Meets His Daddy

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not know about me. I am just not sure how she would re-act. I am bi-sexual male, but have not to much with other males. I also love to cross-dress when I get the chance.

I have been cross dressing for a while now, every since I was 13 or so. I use to wear my moms and sisters things. Now I am few things of my own, plus I wear my wife things too. I love to wear panties, hose, lingerie, dresses, bras, skirts,...pretty much anything. It makes me feel so sexy when I dress up. My wife works day shift, so it makes it easy to find some time to dress.

Wife and I also have lots of toys; vibrators, eggs, anal balls, handcuffs, sex rope and of course lube. I love to have my wife use all of it on me, drives me nuts. I also like to take my wife's tampons and stick them up my ass, get dresses and walk around the house, do some chores. Yet again she does not know about this either. But this story is not about anything to do with my wife.

For a few years now I have been talking with older guy on-line, who also likes to dress too. We have been chatting on-line at least 2 twice a week. I love talking to him, cause he makes me feel so sexy and horny. Makes me feel something my wife can not. We have of course ex-change lots of pictures of each other dress up . I even sent he lots of pictures of me doing myself. We only talked on the phone a hand full of times by now. I even got a web-cam so we could have some fun on there to. We did that a lot of a while. We had always talked about meeting, but it just never seemed to happen.

Well one day we were talking and doing the web-cam thing. When out of the blue he said we actually might be able to meet the next day. I was so excited and nervous when he told me this. I end up that day dressing up sexy for him and getting some toys; playing and fucking myself on the web-cam for him. He told me to be on-line early the next day. After we finished talking, I went and took a shower. I went to work, all I could think about was the next day. I got home from work and went to bed. I had trouble sleeping, of course.

I heard my wife get up the next morning, I waited to hear pull out and leave. I gave her few minutes just to make sure she did not forget anything. I got up and went right down stairs, signed on-line. He was not on yet, I was nervous as hell. I check my mail and did few other things on line. He still was not on-line, I was giving up hope he would show. I got up to use the bathroom. Came back to the computer and there he was. He had sent me message, asking if I was there. I answer him back. He said I could come down today, gave me his address. We both got off-line.

I rushed up stairs and jumped in the shower. I grab my razor and shaved my body complete all over; expect my head. I want to be complete smooth and soft for him. I also made sure to clean my ass out really good too, just in case. I towel off, brushed my teeth. I decide I wanted to surprise him when I got down there. So I decide to wear some sexy cloths under my normal cloths. I went into my wife's room where she kept her cloths. I pick out some red silk stretch boy short panties, with black trim. I slip them on over my smooth soft legs, god it felt good. I pick out a pair of full red fish net pantyhose, along with short silky piece of lingerie to finish it off. I threw on pair of jeans and shirt, a pair tennis shoes. I grab a small over night bag and filled it with all my toys and bondage stuff. Also put in some heels to put on there, some extra panties, lingerie and pantyhose.

I got in the car, put the address in he gave me and started driving. The whole drive down there I was nervous as hell. Kept thinking maybe I should just turn around, what happens if he gave me the wrong address. After about an hour or so of driving, nervous driving me nuts and I had hard on like never before. I pull up in front of the house. I stay in the car for few minutes, trying to get my nervous together. I got out of the car and walk up to the front door. I knock a few times and waited. Felt like forever, just as I was going to turn around; the door creep open.

I heard voice say come in. So I step in the house and the door closed behind me. He stood in front of me in huge bathrobe. Silence for few minutes, then he said I just talk to you on line right. I said yes, it is me. He offer me some wine and cheese, he went into the kitchen to get it. I quickly kick off my shoes and strip of my pants and shirt. I put my bad down, took out some 4 inch black heels with toes cut out on them. I went over and sat down the on couch. He came back out, now he was wearing silk black slip, bra and I assume panties under neath.

He came over to me, sat the wine and cheese down. Sat right next to me, told how sexy I looked. Pick up my wine glass and sip on some wine. We both just sat, sip on some wine, feed each other some cheese, and talked for a little bit. After about 3 cup of wine, he moved closer to me. He sat his hand on my thigh. He told me how soft and smooth I felt. He started to rub my thigh, moving his hand higher as he rub. His hand went under my lingerie piece and start to rub my cock. I moan a little bit as he did. I finish my wine, I place my hand on his thigh. I start to move it up. I felt his silk panties covering his hard cock. I start rubbing it, he moaned as I did. We sat there just rubbing each other.

He grab my hand, stood up and pulled me with him. I reach down and grab my bag as we left the living room. He lead to what seem to be the master bedroom. He lead me to the bed and sat me down. He took the bag and dump in on the floor. He step close to me and kiss me on lips. It was long French kiss, I moan in to his mouth as he did it. He told me I was dirty little sissy and need to be punished. He sat down next to me on the bed, and pulled me over his lap. He held me down as he start to spank me. It was complete surprise to me. He hit me ass check hard and fast. I begged him to stop and try breaking free...even though secretly I wanted more. He told me to stop moving around. He pull my panties and fish nets down. Continued spanking me hard. I start to cry from the pleasure and pain. I begged him to stop, he did.

He rolled over to the center of bed. I pulled my panties and hose back up. He climb on the bed and start to kiss my legs. He work his way up my legs, until he reach my cock. He start to rub his face all over my cock, I start to moan. I motion for him to bring his cock to me. Next thing I knew we were in 69 position. Sucking, rubbing, licking each other panty cover cocks. He pull my cock out of my panties and start to suck it deep. I moaning loudly into his cock. I pull his panties down and start to suck his cock. I could feel him getting bigger and throbbing. I moan to him I was about to cum, and he deep throat me. That was all I need, I shoot my huge load into his throat and mouth. I moan and scream on to his cock, took him as deep as I could. He shoot his huge load into my throat and mouth. After what seem like forever, we both slip out of each other mouths. He roll off me and we cuddled for little bit, and must have fallen a sleep.

I not sure how long I was a sleep for, but I woke cause I felt something weird happening. I was face down In a pillow, felt something cold in between my ass. I felt someone kissing my neck and shoulders. I heard him say, "glad you woke up finally sweetie, I would not want you to miss me fucking you". He bit my shoulder and suck on it. God it felt good, I moaned. He said you want me to fuck don't you, I said yes. I felt his cock head press against my tight hole. He pressed a little hard and it pop right in.

He let me get use the feeling, he start slowly push it in. After few minutes, he was full in. I have to say, it felt great. He told me to hold on, cause he was going to fuck me like sissy boy I was. He start thrust in and out of me, hard and fast. I got up on all fours, so I could feel it better. He grab my shoulders and keep thrusting into me, as he pull me into him too. I start to yell and scream, fuck me daddy...make me your bitch. I start to push back into him, I wanted all over him. He start to moan, I felt him throbbing again, I knew he was about to cum. I tighten up my ass, told him to fill me with his cum. He let loose, filling my inside with his warm cum. Felt like he came forever, finally he slip out of me. He roll me over and he lay me flat on my back.

I was leaking pre-cum like a kitchen sink that was left on. He told me I was dirty little sissy. He said he did not think he would do it, but seeing all dress up and seeing my cock hard and wet. Told me it just drove him wild. He climb over me and was straddling me. He told me hold on, I am going to give a special present. He start to lower himself on to my cock. He was super tight, took a little bit of effort. Finally my cock enter his ass. Lower himself completely on to me. He moan louder then he had all day. Told me how good it felt.

He start to bounce up and down on my cock. I start to thrust up to meet him on the way down, to take it deep into his ass. I saw his own cock start to get hard again, I told him daddy must like this. He just moaned and said, daddy likes his sissy sons cock in him. I start to stroke his cock as he was bouncing up and down. I start to moan and said I am going to cum soon daddy. He told me yes fill me with you hot cum. I thrust up one last time to meet him and shoot my huge load into his ass. He scream and moan as I filled him up. I kept stroking him, he cam again all over me. Covering my face and chest. My cock slip out of his ass. He roll next to me and cuddle next to me. We just laid there, cuddling feeling, and kissing. I told him we should clean up.

He lead me to shower where we strip each other and got in the shower together. We just stood there in the hot water together, holding each other. He hold me kneel on the floor. Next thing I new he start to piss all over me, it felt warm and good. I stood up and grab the soap , washed him off. He did the same to me. We got out of the shower and dried each other off. He told me what a wonderful time he had. I told him I also had wonderful time. I gather my things and got dressed. He escorted me out. I drove home, thinking of everything that just happened. I had to jerk off on the way home due just thinking of what just happened.

Talked to him on line the next day. Both said we would have to do it again soon. How much we love to just spend a night together. How great 2 days of dressing and playing would be. That is for another day. Hope you enjoyed reading this. I know I really enjoyed that day.