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HOT CD Story - A Surprise In Pink Panties

A guy is caught crossdressing by his wife and is taught a lesson he won’t soon forget.

I have always been a cross dresser and enjoyed it. Maybe it was too much at times. I some how let the guys go too far with me. That is a different story. When I got married I put all my special clothes in the basement and lived a normal life.

One day I was home from a trip early and found my wife was doing the laundry. There on the top of the pile were her pink thongs. I was taken aback and grabbed them and slipped them on and the warm rush of my past feelings came back to me. I loved the feel of the silk on my body. I was running my hand across them and soon I was feeling my now erect member and soon it was shooting its results of my rubbing. I took them off and tossed them into the washer and left the room.

 It was a couple weeks later that I needed to go out of town for the night to repair a customer’s computer. As I was packing I took a pair of her panties out of her drawer and took them with me. While on my trip I wore them the entire time. As other trips came up I took more and more of my special clothes. I was soon dressing up and finding new spots to go to and have fun at.

Well if you call having drinks bought for you and hands under your skirt and, well later about that. I was careful to have two bags one normal and one special. I was packing and again took a pair of my wife panties with me. On my trip I wore them and as always enjoyed them.

Sissy Crossdressing whore masturbates while looking at a magazineSissy Crossdressing whore masturbates while looking at a magazine

As usual when I arrived home I would put my special bag in the garage and leave my normal bag in the kitchen. She would empty it and do the laundry and that would be it.

It was several days later that when I went to get fresh pair of  under ware it was when I opened my drawer that there on top of my white boxers was a pair of her panties.

It was the same pair that I was wearing a couple days ago. I was wondering if maybe it was a mistake or something. She said nothing.
On my next trip it was normal. I checked my bag and made sure there were only guy’s clothes in it. Again several days later, when I opened my drawer there I saw several pairs of new panties. A thong, briefs and a low cut boy shorts. I knew something was up now. But what, I had no clue.

It was a couple weeks later when I fond out I needed to go out of town that night that I asked her to pack a bag for me. I arrived home and she was out and there sat my bag. I grabbed it and off I went. At the hotel it was when I opened the bag there on top was a pair of white and pink thongs with a candy kiss taped on them. I now knew it was known to her what I was doing.

I wore the panties all during my trip and enjoyed them a lot. I did not think of whom or what or why, just enjoyed. On my return my wife had made a few comments that could have been taken several ways. I choose the way that I understood them. It got to be a regular thing for her to pack my suit case. Several trips later it was a camisole then a bra.

Sissy Crossdressing whore masturbates while looking at a magazineSissy Crossdressing whore masturbates while looking at a magazine

The time seemed to fly by at a fast pace. It has been two years since the first pair showed up and this last trip the case carried a dress and makeup and heels. The problem that I was having was that it not only made me feel good but, I looked good also. Under the wife’s idea we joined a gym and wanted to keep healthy.

I realize that is a good thing but, truth be told it was different now. I knew that the diet and gym visits where doing there job, but I still wondered. My normal clothes seemed tighter in places and loose in others. I did not think about it. I did think about the bra that seemed to be more practical than sexual. How it now cupped my breasts. I was not wishing I had them I had them. I knew that in t-shirts it looked like I had boobs but that was just wishful thinking. My waist had gotten smaller and my skin was softer and my body hair was thinner. I just figured that with the diet and vitamins that it was just a nice side effect.

My wife had convinced me to let my hair grow and in the sales position I held it did not matter. I was reluctant when she wanted to have both my ears pierced. One had always been pierced since I was a teenager. Now it was both. My wife set up a much deserved vacation for us. It was going to be a month long. If we needed and desired more time, she had included a 2 week extension to the trip. She set up a nice private vacation resort. It was located on a white sands Mexico beach area. She packed the clothes and we were off for much needed rest and relaxation.

We arrived at night and were off to bed. In the morning she said that she would have breakfast delivered to the out side deck area. She told me to shower and get dressed and have coffee on the deck over looking the ocean views. I showered and dried off. With a robe on I went to the bed and there laid out was a two piece bathing suit.

Sissy Crossdressing whore masturbates while looking at a magazineSissy Crossdressing whore masturbates while looking at a magazine

There was also my secret make up. I walked over to the door and saw her sitting drinking a cup of coffee. She was wearing a similar bathing suit. I called to her and asked if there was a mistake. She replied that if I did not do as she requested that it would be a mistake.

I dressed in the suit and fixed my hair and make up. I put the robe on and walked to the door way. I sheepishly walked over to that table and began to sit down. She looked at me and said that robe had better be off when I sit down. I took it off and then she looked at me and said that her work was almost complete. I asked her what she meant. She explained that just after we were married that she had known that I crossed dressed. She also knew that I quit.

It was when I had left her panties in my suit case that she knew I had restarted wearing women’s clothes again. She said that if I was doing that then she would assist in my secret. She explained that several times when I was out of town she would follow me there and see just what I was doing. She told me that the gym was just a way to add a bit to the medical portion of her plan.

I had been taking female hormones for 2 years now and that is why my body made the changes it did. I was in shock, but did not react the way I should have. Within the therapy of female hormones there were additional drugs to smooth my attitude and emotional feelings. That is why I now cry on sappy movies. She told me she created a plan and developed a schedule that was to change me and still be me. We laughed. A little while later our maid came up and surprised me.

There I was in a female’s bathing suit and there was not so much of a blink your eye. She left and we finished the coffee and headed down to the beach. We walked and did some small talk. She did tell me to have fun and she has set up everything. She made it clear that I was to do as she requested. We found several chairs and towels near the ocean. We sat down and relaxed. Close to lunch we placed our order and decided to go in to the ocean.

Sissy Crossdressing whore masturbates while looking at a magazineSissy Crossdressing whore masturbates while looking at a magazine

I was in heaven walking dressed as a lady and it was in the day light. We returned to the chairs and enjoyed our lunch. We decided to walk down the beach a while. There were several cabins and tents in a gathering. We walked up to one of the tents, and were told to walk in and have a seat. Again, no looks towards me. In a minute or two a lovely lady told me to follow her.

I walked behind her and we entered a small shower area and she requested that I get undressed. I slid off my top and stepped out of my bottoms. She turned on the water and from above a warm shower began. She took a wash cloth and soap and began to wash me. She washed every where. While I was lathered up she began to shave my legs and underarms and face and chest. There was not a lot there. She shaved down below into a landing strip design. She then sat me down and someone worked on my hair while they also painted my toes and finger nails.

When I was done she handed my suit back and told me to dress and I was to meet my wife out side by the bar. When I went out side she was sitting down at a table with a couple men in bathing suits. They were talking and laughing.  I sat down and a waiter came over with a drink for me. I took a taste and she had ordered my favorite drink.

I was relaxed in heaven and dressed and shaved and in the sun. I listened to there small talk and had we had several more drinks. I was feeling great. I was becoming very
relaxed and the guy next to me seemed cute. I have no idea where that came from but he seemed cute.  We talked and drank some more. I was feeling dizzy and buzzed and it was nice to feel that way.

The one guy said he needed to excuse himself for a minute. My wife stood up and said that we also needed a minute also. We walked over to the ladies room and entered and used the booths and relived our self’s. As we looked into the mirror she smiled and asked if I was having fun. I said yes.

Sissy Crossdressing whore masturbates while looking at a magazineSissy Crossdressing whore masturbates while looking at a magazine

We walked out and as we sat down she said that the guy was hot and I should go for it. Before I could answer the guys came back and sat down. We ordered some finger food and more drinks. We all talked and laughed. It was then that I realized that he had put hid hand on my leg and was rubbing it and while doing that he was moving his hand up to my thigh.

I was now feeling rather warm and relaxed. I glanced over to my wife and she was watching what was going on and just smiled at me. I felt his hand slide up and then touch my manhood and then slip between my legs. I relaxed my legs and let him slide his hand down further. I had no idea what was going on but I did not care.

The next thing I knew we were standing up with fresh drinks in our hands and walking over to the beach area was they had large umbrellas set up on the beach. We sat on some towels and enjoyed the sun and was soon leaning back and relaxing. I soon felt that hand again and then it was on my belly and then it was on my chest. I turned over thinking I could get some rest and the hand just kept on rubbing me.

He started again on my back and in no time had undid the top and let the straps fall to the side, I felt his fingers slide under the bottoms and begin to ease them down I it did not bother me at all. I could tell they were lower as I felt the breeze over the crack of my ass. I could then feel both hands slide down my bottoms until they were off. He began to spread my legs and started to rub my inter thigh and down my crack.

I was getting turned on something fierce. He then rolled me over and there I was naked to the world. At that moment I wished my member was bigger. It was in the open. I had felt it had been bigger in the past and now my ball sac was very small as well as shaft. I always figured it just grew more when excited and just smaller when not. I felt him grab my now erect member.

I am embarrassed as I know it on al its glory is the size of my little finger. I soon feel him spread my legs real wide and kneel between them. I feel his now wet lips on me and soon he is putting me inside is mouth. I am starting to buck my hips and match is stride. I feel that I am about to cum when he digs is fingers into my flesh and I shoot down his throat.

With in a flash he moves his body up and then I realize that he is naked and is stroking himself. I look down and he grabs my hand and places it on his manhood and I start to stroke it slowly at first then he moves up and he moves so close that I release him and he now has his manhood next to my lips and starts to push it into my mouth. I open my lips and allow him to enter. He starts to slide it in deeper and the withdraw it then enter and withdraw.

I am now hungry for his load and fast. He cum’s rather quick and a lot. While I am in the after glow, he rolls me over and his friend now is moving over and I feel him move in between my legs. I soon feel his finger near my ass and then poking around and then I feel this cool lotion on me and his finger slides in and out and then he moves and straddles me and begins to push his dick in me. I can tell he is rather large as the pain and pressure is intense.

 I feel him enter slowly and with long thrusts picking up speed as he starts his run for the gold. What seems forever or just a minute or two? He rams it all the way and stays there. I feel the cum creating a swelling in me and when he retracts I can feel it leaking down my leg. I am relaxed and content.

I hear movement and my wife leans down to my ear and says that I look like I have enjoyed myself. She then says that this is just a taste of what will be happing for the next month to me. She says that if that is a problem she will just increase the pills and make me beg for it. She laughs and says that is just what she will do…


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  1. Comment by kraftty:

    hi great story i hope there is apart 2 , 3 and more!!!

    February 27, 2009 @ 2:18 pm
  2. Comment by Jim Baker:

    I absolutely LOVE you story! I’ve just recently got into the habit of wearing panties and I am considering doing more crossdressing. You story is definitely persuading me to do it!

    October 8, 2009 @ 3:21 pm
  3. Comment by jo:

    Thanks Jim

    Knowing that you are now wearing panties arouses me. Have you the opportunity to play any games with anyone while you have got them on? Thinking about you reminds me of an ‘arrangement’ that I had with a friend not that long ago.

    I had a fuck buddy, Andrew, who I met on a dating website who loved to wear panties. He was married like me and we would meet regularly at his house at lunch time while his wife was at work. Andrew would always have on pink satin panties when I come over. I could tell that they were not his wife’s because the way they fitted him I could see that he took great care in choosing and acquiring them. They were not really that skimpy. They looked quite old fashioned, like the panties that your grand mother would wear. They had 5″ or 6″ sides and a little bit of lace and a nice little ribbon bow at the front. I would lightly stroke his cock while he watched porn movies (he was a particular fan of straight white guys fucking black women) and when the tip of his hard cock popped out of the top of his panties I would being to lick and then suck his cock. As regular as clock work he would then whisper to me while I was happily sucking away that he would love to fuck a black woman and then he would cum in my mouth. I was always naked when we played, however, he would never touched me or ever returned the pleasure. This was never a problem for me and I would always tell him that there was no pressure and that I did not mind. I was happy because after I cleaned up all his cum he would watch me while I masturbated to a climax, and I course, I got unrestricted access to his cock.

    However, Andrew did break this pattern one day. We were sitting on the sofa watching porn movies as usual and I was rubbing his hard cock through his panties. He asked me to get up and move into a spare bed room that Andrew used as his ‘office’. I agreed and on entering the room I could see, on one side, a built in closet that had ceiling to floor mirrors on it. On the other side was his computer desk. His computer was on and I could see our bodies from our knees up to our lower chests down in a small window. He had his web cam set up and it was filming us. I could see in another window a photo of an attractive white woman in her 40’s sitting back in a comfortable arm chair dressed in pretty black bra, panties, suspender belt and sheer black stockings. Then I see her move and realised that we were hooked up to a live video feed. I was a bit shocked at first but quickly settled down and thought hmm, this could turn out to be something nice. Both Andrew and I were already turned on by our ‘fore play’ on the sofa and I didn’t know what to expect. Andrew quickly grabbed me by my shoulders and turned my back to him. He bent me forward and asked to me to put my hands on the back of a chair. I could feel him smearing some lube on my ass hole and looking into the mirror I could see him pull the band of his panties down over his cock and balls. This was a beautiful sight as the rubber of the panty band sat under his scrotum holding his balls and dick like a very pretty pink, silky, cock ring. His cock was engorged now and was incredibly thick with the glans penis turning purple in colour. I then felt him put the head of his cock against my rectum and with one quick push slid it past my sphincter. I yelped a bit because because my as had not been loosened first and the action was so quick and it did hurt a little. But it was only seconds later that the pain subsided and was replaced by absolute pleasure. He started fucking me like he was a man possessed . I could not take my eyes of what Andrew was doing to me in the mirror. His ass was moving back and forth with his wet shaft sliding in and out of me. I could see my hard cock flaying around from the force of his fucking and making slapping noises as it hit my stomach. This rhythm was counter pointed by the noise Andrew was making as his balls whacked against mine, his tummy smacking against my ass and the moans that both of us were emitting. I was in absolute heaven now and I had lost all sense time and where I was. But all good things must come to an end and, much too soon when I think about it now, I could feel my passion well up in me. Without even touching my cock I began to squirt thick in globs of cum on to the floor in time with andrews thrusting. Just as the last drops were dripping from my cock I could feel Andrew’s dick thicken inside me and his body shudder. His rhythm changed and was replaced by hard, sharp thrusting as he shot his cum deep into my bowels. He rested for a moment then slid his rapidly wilting cock out of my ass his cum began to leak out of my satisfied fuck hole to join the pools that I already left on the floor. I then remembered the woman on the computer. I looked over at her and I could see her sitting back deep in her chair, but this time with her panties removed. She was licking her fingers had a very contented look on her face. Even it the small window I could see that her natural cunt was swollen and glistening with fuck juice.

    Andrew and I changed pleasantries as we always did after a session together and we agreed to email each other and make another time to meet. I left him for day and went back to work. I emailed Andrew a week or so later to arrange another meeting but my email was returned and marked ‘undeliverable’. I tried to contact him again over the next few weeks but still was unsuccessful. The time when Andrew finally decided to physically pleasure me by fucking my ass was the last time that I saw him. Still today I wonder why he disappeared?


    February 26, 2010 @ 11:37 pm
  4. Comment by Jamie:

    WOW. How lucky can one man be. The images you described will last a lifetime
    In my mind.
    I believe I am beginning th journey. I wear panties 24/7. I also wear sports bra,s daily unless I go clubbing, then I wear my Victoria secret lacy thing. I am sorry I don’t have a wife to share the journey. I hope to find a suitable understanding woman.

    April 11, 2013 @ 12:12 pm

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