Caught cross-dressing by my wife

I have always been a cross dresser and enjoyed it. 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 knickers. I remembered I loved the feel of silk on my body. She left the room and I picked them up and I was running my hand across them and soon I was feeling and rubbing my cock which quickly became erect. All too soon I was shooting the results of my rubbing into my pants… a nice warm sticky mess… well I tossed her knickers back on top of the laundry pile and went to change my very wet underwear!

It was a couple weeks later that I needed to go out of town for the night to visit a customer. As I was packing I took a pair of her knickers out of her drawer and took them with me. While on my trip I wore them the entire time and spend very enjoyable evenings feeling myself and cumming in them. As other trips came up I went back to my box in the basement and took more and more of my special clothes with me. I was soon dressing up and finding new spots to go to and have fun at… bars where I was having drinks bought for me and hands trying to get under my skirt and, well, I’ll come back to that a bit later…. I was careful to have two bags one normal and one special.

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 found 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 knickers with a candy kiss taped on them. I now knew it was known to her what I was doing.

I wore the knickers 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.

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 in order to keep fit and healthy. I also started eating differently/healthier.

After several months, I knew the diet and gym visits where doing their job. My normal clothes seemed tighter in places and loose in others. I did not think about it. The only thing that perplexed me was that in tight t-shirts, it looked like I had boobs… or was that 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 outside deck area. She told me to shower and get dressed and have coffee on the deck overlooking the ocean. I showered and dried off. With a robe on I went to the bed and there laid out was a two piece bathing suit. There was also my secret make up.
I walked over to the door and saw here 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 makeup. I put the robe on and walked to the door. 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, well, at least for a while.

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 learned 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 d**gs 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 to being more feminine. Well, I just laughed.
A little while later our maid came up and surprised me but whilst I was in a female’s bathing suit, she didn’t blink an eye, as if what I was wearing was perfectly normal.
She left and we finished the coffee and headed down to the beach. We walked and did some small talk. She did tell me that she wanted me to have fun and she had set up a few surprises. 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.
I was in heaven walking dressed as a woman and it was in the daylight. 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 strange 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 everywhere. 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 outside by the bar. When I went outside she was sitting down at a table with a couple of 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 favourite drink.

I was relaxed and in heaven, dressed and shaved and in the sun. I listened to their small talk and after 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. We walked over to the ladies room and entered and used the booths and relieved ourselves. As we looked into the mirror she smiled and asked if I was having fun. I said yes.

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 hand on my leg and was rubbing it and while doing that he was moving his hand up to my thigh.

After all the drinks, 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 further up my thigh and I couldn’t help but open my legs a little. He moved his hand still further and…oh my god…he touched my cock...then slid his hand up and down, up and down between my legs. I was now getting an erection so I relaxed and opened my legs a little further as I wanted him to touch my cock again…and again…oh wow, this was really turning me on and as I looked over at my wife again, she just smiled. I had no idea what was going on but I didn’t care!

I was well on the way to making a mess in my swimsuit…and really wanting to, even in public, I was so turned on but, the next thing I knew we all got up and were standing with fresh drinks in our hands and walking over to the beach area where they had large umbrellas set up together with windbreaks creating quite a secluded area.
We sat on some towels and enjoyed the sun and I was soon leaning back and relaxing again. I soon felt that hand again and then it was on my belly and then it was on my chest. Suddenly conscious of the fact we were on a public beech, I turned over but he just started rubbing my behind, and, oh boy, did that turn me on yet again…

He then started on my back and in no time had undid the bikini top and let the straps fall to the side, I felt his fingers slide under the bikini bottoms and begin to ease them down.
Despite being on a public beech, I realised the large umbrellas hid us quite well so what he was doing wasn’t bothering me so much anymore, And besides, I was so turned on by this time that I could feel I was just seconds away from shooting my load!
As he eased my bottoms down, I could feel the light breeze over the crack of my bottom, and he then fully removed my bikini bottoms, sliding them down and off my legs. I then could feel both hands slide up my inner thighs and he then started to spread my legs and began to feel the tip of my cock, groping and massaging and then he went back to my bottom, moving my cheeks apart slightly as he ran his fingers up and down my crack. I just couldn’t help it…I came right then, I came like I’d never cum before, I thought I wouldn’t stop cumming. If I hadn’t been lying down I would have collapsed from the sheer ecstasy of how he had made me feel. I felt so embarrassed I started to sob a little but he said it was OK. He was glad that I liked what he did.



He then rolled me over and there I was naked to the world. At that moment I wished my (now limp and floppy) member was bigger. It was in the open. I had felt it had been bigger in the past but then I had nothing to compare it with and not only that, my ball sac was very small as well.

He then put his hand on my limp cock which was now the size of his little finger. He started to massage it and play with it and I started to feel myself getting hard again. He then spread my legs real wide and knelt between them. I felt his hot wet lips on me, kissing my belly and moving downwards and soon he is putting my cock inside his mouth. As he moves his mouth up and down my hardening shaft, I start to buck my hips and match his moves. I feel that I am building up to cum, again, and as I continue to buck against him he increases his pace going faster and faster and then, oh god, I’m cumming, I’m cumming, I’m cumming and I shoot down his throat. Oh fuck! But that was good!

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 again.

I am now hungry for his load and when he cums, it’s quick and it’s a lot. I swallow as best I can and he finally stops spurting. He pulls out and lays beside me. While I am in the afterglow, still quite dazed with what’s happening and not really aware of my surroundings, he rolls me over on my front and his friend has left my wife and is now is moving over.

He lays besides me and I feel him place his hands on my butt cheeks and move them apart. I feel something cool, a lotion, being applied to my virgin hole and he starts to open my legs further and then to slide his fingers up and down my crack, fingering my virgin hole again and again until he slides a finger inside me, in and out, in and out and OH what a feeling… and then if feels like two or three fingers inside me, opening my hole, a little painfully I have to say but I didn’t want him to stop…and I was getting hard again!!

And then he moves and straddles me and begins to push something much bigger into my tight little hole, oh! I realise it’s his cock! I really hadn’t thought or planned for this and as he continues to push, I can feel my virgin hole slowly opening up to allow him into me. I can tell he is rather large as the pain and pressure is intense at first.

I feel him continue to enter slowly and then start to move in and out, back and fore, with long thrusts, picking up speed. He’s now really fucking me! Going quicker and quicker and I just know that this is going all the way. I’m frightened and excited at the same time. My hand goes down my front. I’m desperately trying to grab my cock as I’m absolutely desperate to cum…again!

His strokes are getting longer and faster. His breathing is getting louder and harsher. I realise there’s no stopping him now. He’s going to cum inside me! I finally get my hand to my cock and I’m now wanking as best I can, lying on my front and I can feel my excitement and my cum starting to boil…

What seems like forever, or just a minute or two? He suddenly rams his cock all the way in and stays there. I’m sure I can feel his cum creating a swelling in me and I’m so turned on by this that I cum as well…again, for the third time.
He starts pushing again, gently this time and I can feel he’s softening and then he pulls out slowly, leaving my tight virgin hole a tight virgin hole no longer. As he pulls out fully, I can feel his cum leaking down the crack in my bum and coating my balls. I reach back and feel the wetness there and pull my hand away, soaked in his cum…and place it in my mouth to taste it.
I can’t move, I’m drained. But I’m 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 happening 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…but, I’m wondering where she keeps the pills :-)