On Vacation
My name is John Johnson and my wife of ten years is Sue. I have been interested in cross dressing since about 10 years old when I would try on my mothers panties when she was not home. I remember when I was younger than that when I was 3 or 4 and my mother would be sitting at the table talking to one of my aunts, I would stand beside her and rub her stockings. I think that is what started my fixation with all things silky. The first time I masturbated was wearing a pair of my mothers panties, I didn't know at the time why I liked it so much. Over my teen years I would try to wear something silky when ever I could. Growing up I dated girls and acted heterosexual like all other boys but I still had a warm spot for my pretties.
I met Sue in college and hit off right away. We married right after graduation, she was a art major and I was a business major. We were like two peas in a pod, we were both 5 foot 8 inches and and on the slim side. I know we were about the same size because she borrowed my jeans a couple of times and they were only a little loose on her. Early in our marriage when we went shopping she would notice me fingering the silk panties and silky blouses in stores. One night after shopping we were getting ready for bed and she brought out a little box and gave it to me.
"I saw the way you were touching things and thought you might like a pair or two for yourself".
I opened the box and found a pair of black and red panties. We had always been open with each other and blushed and said, " I'm a little embarrassed but I have always had a soft spot for silky feeling things." I proceeded to tell her about my fixation with my mothers stockings and masturbating in panties. She told me it was OK and it was even a little exciting to her. That night while I wore my new panties we had great sex. She rubbed me through the panties and licked my penis through the panties, I don't know who was turned on the most me or her. Over the next few years she showed me how to become more and more feminine. During that time I had a old uncle that died and left me, his only relative other than my parents, a sizable inheritance. I was able to quit my job working in a office and start a consulting firm from home. I was doing well with that and Sue was working part time for a art gallery in the city. We were doing good and had time to ourselves. I exercised and ate right trying to keep my shape as feminine as I could. I made sure my body was hairless at all times and let my hair grow down to my shoulders and wore it in a pony tail.
Sue showed me how to put on makeup in different styles and with my hair down I passed fairly well. We even went out to lunch and dinner a few times and I never had a problem. We had a great love life and she said it was nice having a girl friend and husband in one. She said she had the best of both worlds. I usually wore something feminine when ever I was home usually pantyhose, bra and panties. I wore skirts and tops and flats while working in my home office. It was very nice. Once a week we would dress to the nines and have a hot sex session. But that is a different story.
Our tenth anniversary was coming up and Sue said over dinner one night that she wanted to do something different and exciting. She said she had been thinking She said that she only loved me but thought we needed to add a little spice in our life. She had been thinking and she wanted to go away somewhere as two girlfriend and have a wild time where no one knew us. I was a little hesitant and asked her if she wasn't satisfied with me anymore. She kissed me and said no way, but a little diversion could be fun. She said she would like to try a stud or other woman and that she thought it would be hot to see me with a stud myself. I had fantasied off and on while dressed what it would be like with a guy and said maybe we should. We decided on New York City because there were a lot of stores and theatre to go to also a lot of bars and restaurants. I knew I couldn't pass on a airplane so we decided to drive, it only being a two day drive and maybe we would stop over in Atlantic City on the way, seeing how things went. Sue got on line and found us a really nice hotel in the heart of the city with reasonable parking underneath. We decided to leave the car and use taxis once we arrived.
The day before we were leaving Sue said she had thought about it and that we should stop in Atlantic City on the way also. She wanted to have us both go to a spa and have a makeover before we went to New York. She said she wanted to see my hair cut and styled in a more feminine way and have our nail done. I thought it was a super idea and started to look in some woman's magazines for hair styles I would like. We found a few. We left and made it to Atlantic City in enough time to check in and make a spa appointment. It was great girly fun, I had my fake fingernails applied and a pedicure . I had both my fingers and toes painted a dark red, it looked very sexy. They cut and styled my hair and highlighted it also. Wow, was it ever feminine, I was in heaven. After Sue said we should dress up and try out our new styles. I wasn't expecting to go out sexy so soon, but in for a penny, etc.
We dressed in matching sweater dresses with scoped necklines, mine in black and hers in white. I wore black panties and bra with a push up that gave me nice cleavage for a small breasted girl. Sue looked marvelous with her breasts bulging out of her top. We both elected for pantyhose due to the sweater dresses and it gave me a way to help hide my little guy. We both had just purchased 5 inch platform heels that gave us long sexy looking legs. We made up for night time with a slightly sultry look. Jewelry and a spritz of perfume and we were on our way. I was a little nervous but I had passed before and looked more feminine that I had ever before. We went down to the restaurant and had a nice meal and decided to do a little gambling. We were standing at the roulette table and I know I felt a hand or two brushing against my rear, it was exciting but I didn't do anything. I noticed a hunky guy watching me as we gambled and when I whispered this to Sue she said she also had a guy looking a her too. We decided to go to the lounge for a drink and on the way I said how far do you want to go tonight. She said it was up to me and our secret code to leave would that we were expecting a phone call from our husbands.
We sat at the bar and ordered two white wines, crossed our legs and looked over the scenery. There were a few single men around but nothing exceptional. Soon the two men from the casino walked in and I have to say they were both hunks and I wouldn't mind being with either one. They walked over to us and said they noticed us in the casino and that we were the best looking women in the hotel. I blushed and Sue giggled, we said thank you guys, your not so bad yourselves. They sat next to us on either side and we turned towards them. I introduced my self as Johanna and he said he was Dan. He also was the hunk who brushed up against me in the casino. I thought he was very handsome, about 6 foot tall with slightly curly hair and fit but not overly muscular. Just the kind of guy I have fantasied about. I was nervous but confident that I passed and that my voice was husky but feminine. He said he was glad to meet me and that he and his friend, Jim, were here at a weekend getaway for their bank and lived in New York City. I said we were going their shopping but stopped in Atlantic City for the night.
The boys said why don't we get a table and have another drink and maybe dance. I looked at Sue and she smiled yes so we moved over the a secluded table in the back of the bar. There was a combo playing music and several people were dancing. Dan asked me to dance a slow dance and I said OK but I wasn't a big dancer. He took me out onto the floor holding my hand, I felt so feminine. We danced and he pulled me close to him and I laid my head on his shoulder. I fit nicely against him and could feel his manhood starting to grow. I loved that I was making a man excited but had to be careful about my self. It was a good thing I had a gaff on and was strapped in good. I notice Sue dancing also and that she was rubbing up against her guy also. I was really enjoying being a girl in a mans arms. We went back to the table and when we sat down Dan put his had on my leg and started to rub my stockings, I thought I was gong to cum, it felt so good. He leaned over and kissed me and whispered that we should go somewhere quite later. I told him I would think about it and would have to talk to Sue. In a little while we excused ourselves to go to the ladies room. When we got in there I said what Dan and asked and she said Jim said the same to her. She said that she wouldn't mind a little fun with Jim, when they danced she could feel his largeness against her and it felt good. I said Dan felt good too but I was nervous but could probably handle him. l wondered what Sue thought of me doing this and that I was a little worried that she might find someone else to love. She told me I was silly and that she loved me and the best of both worlds we had. So I said OK lets go for it. She said Jim told her they had a suite and that we could go there for drinks and it had a large living area overlooking the ocean with a balcony and two separate bedrooms if something developed which she hoped did.
After a few more drinks and dancing Dan said would I like to go the their room for a nightcap and I said sure. We walked out hand in hand and when we got in the elevator he put his arms around me and grabbed my small but cute breasts and started to rub against my rear end while kissing my neck. I almost swooned. We reached their room and it was beautiful with a large deck overlooking the pool and ocean. Dan said he didn't have wine but how about a brandy. I said it sounded good and walked out on the balcony. Sue and Jim were on the couch necking and feeling each other up. Dan came out on the balcony with out drinks and said kiss me if you want your drink. So I stepped into his arms and kissed him for all I was worth. He put the drinks down and put his arms around me. He stuck his tongue in my mouth and I met him with mine. We had our drinks and he had me face the railing while he rubbed against my rear. I felt great, we sipped our drinks for a while and when we looked back Sue and Jim were gone. Dan took my hand and pulled me into the living room and sat on the couch and pulled me onto his lap. I was sitting cross ways on him and he started to neck with me again and started to rub my stocking legs.
I started to worry that he would find me out and tried to remove his hand but he kissed me and said that Sue had told Jim about me and that this was my virginal time out. He said he always wanted to meet a gurl like me, but never thought he would meet someone as beautiful as me. I was shocked at Sue but also happy that it was working out. I kissed Dan all over his face and mouth loving it. I moved over on to his lap so I was straddling him, I pulled my dress up and I could feel him rubbing me between my legs. I was hot and getting hotter. He opened my blouse and kissed down my chest to my cute little breasts and he started to suck and nibble my nipples. I started to whimper and put my arms around his head and pull him into my chest. I was humping against him getting hotter and hotter. I could feel my pantyhose tight against me and he started to rub my legs. I started to cum in my panties and I squealed. I felt like I was going to faint. I was a sexy, beautiful girl with her lover. It felt so right.
"Oh, Danny, I love it, I'm cumming." I squealed. I came and came soaking my panties. I collapsed against him trying to catch my breath. I calmed down a little and slid off his lap and almost tore his pants off him trying to get to his penis. I wanted it so bad.
I tore his pants down and his briefs off. I wrapped my hand around him marveling at how my painted nails looked holding the first penis other that my own. I leaned down a licked the precum off him, it tasted wonderful. I slowly licked down him and back up the other side. He had his hands in my hair rubbing my head and telling me how much he liked what I was doing. I took him in my mouth, I was finally where I wanted to be, I sucked him and thought I was made to do this I sucked and licked him for all I was worth I wanted him to be pleased with me. After about fifteen minutes he said he couldn't hold it any longed and held my head still while he pumped stream after stream into my mouth until it ran out the edges. I couldn't swallow fast enough but I wanted all of his sperm in me, he tasted so good. When he finished I licked him clean and crawled up into his lap again. I laid my head on his shoulder and kissed his ear telling him how much I loved his cock. He said that he wanted me to stay the night with him because there was much more he wanted to do to me. I told him anything, anything lover. He said he was sure Sue would like what Jim had to offer and would probably stay also. He grabbed my hand a said," Come on beautiful, it time for bed. He He.
We went into his bedroom and he started to kiss me and hold me against him while he felt my butt and started to pull my dress up. I said I'm wearing pantyhose and needed to take them off . He asked if I minded if he ruined them by cutting the crotch away because he liked the feel of them on me. I said that was fine I liked the way the felt also. He told me there was a small pair of scissors in the bathroom, so I went in to clean up and pulled down my pantyhose and cut the center out. I removed my panties and washed them in the sink so I had something to wear later. I fixed my makeup and applied a extra heavy coat of lipstick, I wanted to leave kiss marks all over him. I came back out and he was laying on the bed naked, with a large marvelous penis sticking straight up in the air. I asked if that was for me.
He growled," Get over here lover, Daddy wants to show you some love.".
I took my dress off but left the rest on and crawled up the bed from the bottom, purring, here I come daddy. I crawled up kissing his legs, thighs and finally his balls and then his penis. I engulfed it in my mouth, licking it.
Danny said, "Be careful honey, I want to make you my woman, don't make me cum too soon."
I straddled his lap and slowly lowered myself down onto his marvelous penis. I was a tight fit and hurt a little until it passed my anal ring. It was a good thing I had a lot of practice with my dildo. I felt him slide deeper and deeper into me. I felt like such a woman. I wanted to be his slut and not stop. I felt full and happy. I started to slowly move up and down on him as he grabbed and massaged my breasts. I leaned down and kissed him.
"Don't stop lover", I said. "I'm yours, fuck me, fuck me.
He kept it up for ever, we changed positions and I lay on my back and wrapped my legs around him. He kept pistoning in me for a long time. My little guy was leaking onto my belly, I was trying to hold back until he was ready. Soon he started to breathe harder and said he should pull out he was going to cum. I told him I wanted him to cum inside me, I wanted to be his woman. He let go, spurt after spurt inside me. It was enough to make me cum between us. Wow. We lay there catching our breath and kissing each others faces. I loved it. I told him I wanted more in the morning and he said so did he. We snuggled in each others arms and drifted off to pleasant dreams.