While this is a fictional story a few things are true. My wife Lady Colleen does have a friend whose name is Christine. Being friends since childhood means that Christine really does know of Amanda. In fact one of the more humiliating things that has ever happened to me was when I found out Lady Christine knew of Amanda. My wife then girlfriend handed me the phone and said Chris wants to talk with you. Christine then asked if I had seen the latest Victoria Secrets catalog. When I said no she told me the picture on the cover was of a model wearing "boy short" panties and that there was a sale on purchases over $50. She giggled and said don't you think that would be funny a boy in boy short panties? She then asked if I wore boy short panties and if I would like to order any with her so that we could take advantage of the sale. Up until that moment I had thought Chris now Lady Christine was unaware of my dressing. Her comment about boy short panties was also the seed for the fantasy.

Any way on to the fantasy. I have a lot of fun shopping for lingerie and one of my favorite places to shop is Walmart. I also love shopping for bras and panties marketed at teen girls. Something about the colors and styles turns me on. One day while shopping I started to have this fantasy where Lady Christine took me shopping for back to school clothes. As we walked through Walmart Lady Christine poked through the rack of dresses and such. The back to school ads and posters were everywhere. In the intimates department women were shopping with there teen daughters and I followed Lady Christine to a rack of matching bras and panties. There Lady Christine picked up a blue lace bra, she looked at the size and held it up to my chest. What size bra do you wear? I lowered my head and answered a 40 C my lady. She snapped back I am sorry I did not hear you, what size bra do you wear sissy. As I looked up to answer a second time I could see two women and a couple of teen girls looking at me awaiting the answer. The answer, louder this time, I wear a 42c my lady got a couple of laughs and a look of disgust.

We then wandered to a second rack were Lady Christine handing me another bra. She also picked up the matching fishnet boy short panties. She giggled and said do you wear "boy short panties"? Don't you think that is funny, a boy wearing boy short panties. I turned bright red as her voice was loud enough to be heard by several shoppers. A few moved away but one woman continued to shop close by. Lady Christine then picked up a third bra from the same rack. This one was pink and came with the same fishnet style boy short panty. As she held up the second set, the bra to my chest and the panties to my waist you could hear the woman giggling under her breath. Lady Christine then turned and said "I know isn't it funny but his wife likes him in pink". With that she handed me the third set. We continued to shop for several minutes. Lady Christine picked out a couple of sun dresses which were held up to my chest to see how they would look. The colors were compared to the bra to see how they would look together.

I then followed her to the dressing room. There she took me into a dressing stall and had me remove my tee shirt. She handed me the first bra and had me put it on. After checking it for fit she snapped as picture with her phone and sent it to Lady Colleen. The first bra was exchanged for the second and then the third. The two sundresses were also tried on for fit. All were photographed and sent to my wife for her input on fit and style. When we were done trying things on Lady Christine handed me the bras and matching panties and had me put back on my tee shirt. As we headed to the check out and I thought my humiliation was over. However unlike when I shop alone we did not use the self check out. Instead we stood in line with me holding my soon to be new lingerie. As we approached the register I laid the bras and panties on the conveyor. The young and very pretty sales clerk smiled and looked a Lady Christine. As she looked at Lady Christine she smiled she said these will look cute on you I am sure your husband will like them. Did he chose them for you? Lady Christine laughed and smiled and replied. He is not my husband and these are for him. They both got a good laugh at the answer. Lady Christine then took one last swipe when she said you wanted them so you get to pay for your new undies. My humiliation was complete and we left.

So I did buy the bras and panties that day but with much less exposure and without trying them on. The fantasy was still fresh in my mind as I stood on the deck trying each bra and panty set on. The video was the result of the shopping trip and my fantasy that day. I hope you enjoy both reality and fantasy.

My wife and her lover Lord Gregory have a great deal of fun at my expense. They seem to get sexually excited by humiliating me. More often than not this is done by sending or taking me shopping for lingerie or toys. Lord Gregory has a thing for garter belts and stockings. They then have fun making me match bras and panties to the barter belts and take pictures to post here and on Flickr. On one occasion Lord Gregory was boarded with the everyday black garter belt I wear most of the time. So on a Saturday afternoon he stopped by the shop and he took me shopping. It was summer and prior to leaving to go shopping Lord Gregory took me to the house where he had me put on a matching bra and panties, garter belt and stockings. I was mortified when he handed me a pink ladies tee and ladies shorts to wear. No hair, no make up just me dressed in ladies clothing. My bra and stockings obvious to anyone looking my direction. He just smiled and said there now we will be able to see how a new garter belt will look and fit if we find something I like.


Lord Gregory then took me to a local kink shop because he knew they would let me try on things for fit. We walked from the car maybe a block to the shop which is located on a city street. Several people noticed what I was wearing and I could see from the smile on Lord Gregory's face that he was enjoying my humiliation. Once in the shop the sales clerk who couldn't help but notice what I was wearing asked if she could help. Lord Gregory explained that he wanted to purchase a garter belt for his girlfriend as a gift and that he had brought me along as a model to see what it would look like. The clerk got a good laugh and they picked out a few for me to try on. I tried on each garter belt in the small dressing room and modeled each one for them by coming out on to the sales floor in just my lingerie. As I came out of the dressing room wearing the second choice I could see a young lady who had entered the shop. she just smiled and remarked how cute I looked. He took a picture and texted it to Lady Colleen who approved of the purchase. Here is a picture of the garter belt which Lord Gregory purchased.


When we arrived home I was still wearing my new garter belt and Lord Gregory was very excited so I got to do my favorite thing. I stripped down to my lingerie while Lord Gregory undid his jeans, I dropped to my knees lowered his boxers and began to tease the head of his cock with my toung. As I sucked him into my mouth I could feel him growing hard. He got so incredible hard and he dripped precum by the gallon. Unlike most times he climaxed after only a few minutes with the biggest load of cum I have ever swallowed. I guess hamulating me really is a turn on for him.

Over the years he and Lady colleen have purchased me several garter belts. Most come in the mail and I get to try them on, take pictures and wear the ones Lord Gregory likes best when he comes to lunch on Thursdays. When ever I put on that black garter belt with the flowers I can't help but think of that Saturday afternoon.

Here are a few pictures of garter belts the have bought for me.




As always some fact and some fiction. so....... Fiction; Lord Gregory didn't take me shopping. I did buy the garter belt at a kink shop and I did try it on but I did not go shopping in ladies lingerie and clothing. I have worn all the garter belts in this post for Lord Gregory when he has visited for lunch.

For the past several years my wife has been seeing her lover Lord Gregory. It is not an everyday thing or even an every week thing. My wife, rightly so, enjoys the physical pleasures of sexual intimacy and I am for whatever reason unable to provide her with what she wants. While not my first choice I do understand her reasons and therefore except life as it is knowing that I am and always will be her first and only love. This realization has freed us from the conventional norms of marriage and has awakened feelings and desires previously hidden from view. The result has been a relationship which has given all three of us physical pleasures unavailable to so many. At the top of the list for me is sucking Lord Gregory's cock at lunch on my day off. For Lady Colleen it is well the obvious. I never get to witness their love making nor do I have any desire to do so. And while there are lots of pictures of me neither Lord Gregory or Lady Colleen are willing to be photographed, even partially. All though I am fairly certain Lord Gregory has one or two pictures and videos of me on my knees with his cock in my mouth and cum all over my face.

So one might ask why all the pictures. Simply put, they are used by Lord Gregory and Lady Colleen to choose outfits for me to wear when Lord Gregory come by for lunch. I post them here, on Flickr and Xhamster because I like hearing what people think. As a general rule I have Wednesday afternoon and Thursday morning off from work. Both Lord Gregory and Lady Colleen enjoy hearing stories of my humifaction and shame. So both will set tasks for me that can and do result in my public humiliation. Very often this means sending me shopping on Wednesday afternoon. They will assign me a specific type of clothing to purchase, matching bra and panty, sexy lingerie such as a sheer nightie or a pretty sundress. They will also tell me where to go shopping, Walmart for cheap things, Macy's for hard to find items such as garter belts or the adult book store to find the trashiest stripper lingerie. Simply shopping for a bra and panty set can result in humiliation.

While shopping at Target one afternoon I was poking through the drawers searching for the correct size thong to go with a pretty pale blue bra. As I searched a woman shopper walked over and picked up a light blue and white thong and held it up. She looked to her friend and said "these are the most comfortable thongs I have ever worn". Her friend smiled and agreed they looked comfortable. With that the first woman handed me the thong, smiled and said I think a large will fit you nicely. As she laughed and walked away she said to her friend "they are definitely for him. If you look closely he is wearing a woman's tee shirt and a bra. No doubt he is already wearing panties". I turned beat red with embarrassment but could say nothing as everything she had said was true. Upon hearing the story of what happened Lady Colleen and Lord Gregory insisted on a picture to show them what had been chosen for me. This is also what I wore for Lord Gregory's lunch visit the next day.


As time goes on I hope to post stories of my adventures. Some will be 100% true and others will be slightly embellished I hope you don't mind. For instance in the story above the two young ladies were shopping, One did come over and pick up the thong I am wearing in the picture, looked at her friend and describe them as comfortable but she did not hand them to me and tell me they looked like my size. Rather she put them down and looked at me with one of those knowing looks of I know you are shopping for yourself. As she walked away they both looked at each other with one of those under your breath giggles that couldn't be contained. So I am sure she figured it out and yes I was wearing a ladies tee shirt which was lose fitting with a cute bralett underneath. The lose tee hides the bralett unless you look really closely. Both along with the thong panty I was wearing were left out by Lady Colleen with instructions on where to shop and what to shop for.

After that first night that Lord Gregory spent the night and the first time I sucked his wonderful cock it was clear to me , my wife Lady Colleen and her lover Lord Gregory that I was a complete total cuckold sissy fagot. As Lord Gregory was getting ready to leave the next day Lady Colleen announced that he would be stopping by the house on Thursday (My day off) for lunch. I was to do as I was told without question as if the directions had come from Lady Colleen herself. On Thursday morning Lady Colleen got up and prepared for work. I got up and fetched her a cup of coffee and waited in the bedroom for her to finish her shower. When she returned to the bedroom I dressed her as any good ladies maid would have. When I finished dressing her I stood in front of her and she placed me in chastity for the day and reminded me that Lord Gregory would by promptly at 12 noon.

When Lady Colleen left for work I headed to my sissy bedroom to find what Lady Colleen had laid out for me to wear. There I found a note instructing me to put on my maids uniform along with a very plain bra and panty set. I then set about the days tasks which included laundry, cleaning the bathrooms, vacuuming the rugs and dusting the rooms. At around 9;00 pm I was mostly done with my chores when I received a text on my cell phone. Lady Colleen instructed me to go back to my sissy bedroom where I would find four bra and panty sets laid out on the bed (I had seen them earlier). Each set was to be put on with the accompanying garter belt and stockings. Each set was to be photographed outside on the deck. One picture from the front, one from behind and one from the front with my panties pulled down to expose my caged sissy clit. Lady Colleen calls this front back down and the pictures are combined to make one picture. You will notice this format for several of my pictures here. Each outfit was then to be sent to Lady Colleen so that she could chose the outfit she wanted me in when Lord Gregory arrived.

On this day Lady Colleen choose a leopard print bra, thong and garter belt. Leopard print is one of Lord Gregory's favorite. What I was unaware of until Lord Gregory's arrival was that Lady Colleen had forwarded the pictures to Lord Gregory who had a say in what I was to wear. Here is the set.


At 12 noon Lord Gregory arrived at the front door. I opened the door and stood still for his inspection. He smiled and told me to turn around. Sissy fagot I understand there is leftovers from your wife's dinner last night that are to be my lunch. Yes Lord Gregory let me reheat them for you. Lord Gregory sat at the bar in the kitchen and ate lunch while I stood by awaiting his instructions. When he was finished eating he turned to face me and said now it is time for your lunch and my dessert. He stood and undid his pants. As they fell to the floor I could see his cock was already starting to bulge in his boxer shorts. I quickly feel to my knees and lowered his boxers to expose his growing cock. I had been denied the pleasure of finishing him on Saturday night and I was determined to get what was mine. I slowly began to lick the head of his cock taking it into my mouth. As I sucked him in I could feel him getting harder and I could taste the precum oozing from the swelling head. Nothing makes me hornier than feeling my man's cock grow hard in my mouth. The thought that he finds me sensual and the idea of what is to come is almost to much for me to take. Lord Gregory is a wonderful lover with lots of stamina. I worked his wonderful 8 inch cock for more than fifteen minutes. Just as I thought I would be denied again he pulled his cock from my mouth and jerked his cock so that he shot a gargantuan load of cum into my mouth and all over my face. I did my best to swallow and lick up every drop but could not. He looked down and said good sissy. I love it when you act like a slut. With that he dressed and left.

Yes I was left locked and found no relief but that is ok as a sissy my job is to please not be pleased. This has become a regular routine. Each Thursday Lord Gregory stops by and I am dressed in the outfit he and Lady Colleen choose in the morning.

A couple weeks after meeting Lord Gregory Lady Colleen announced that we would be hosting dinner for Lord Gregory. On the prescribe day I was sent to my sissy bedroom to dress. There I found my French maids uniform. Snice we were home for the day I was already in my chastity cage. After dressing I set the dinner table for two, chilled a bottle of wine and prepared dinner. When things were ready I was instructed to wait by the door for Lord Gregory's arrival. At 5 PM promptly the door bell rang and I opened it to greet Lord Gregory. He had a very pleased smile on his face as I stood there in my uniform. Lady Colleen came in a greeted him with a very passionate kiss which was for my benefit. She turned and gave me a look that said I no longer need your tiny sissy cock for my physical pleasure. In fact we have never had sex since she brought Lord Gregory home that night. As I stood there Lord Gregory had me turn around and lift my uniform and petticoat so that he could see I was properly dressed and caged. This is one of the pictures Lady Colleen took that evening.


We retired to the living room and I served drinks. It was at this point that I started to learn about Lord Gregory. He is 6 foot tall slender but very well built. He has blonde hair and blue eyes and is approximately 180 pounds. Lord Gregory works in banking and his office is only a few short miles from our house. This is also when I learned the most important fact about Lord Gregory, he is like Lady Colleen, bisexual. After a few drinks Lady Colleen sent me to the kitchen to prepare the balance of the meal which I then served to them in the dining room. After each course I stood in the corner and when requested I poured more wine. When dinner was finished they returned to the living room and I cleared the table and did the dishes.

When I returned to the living room I found Lady Colleen in the couch next to Lord Gregory. Her blouse was open and it was clear that he had been foundling her breasts. He also held the key to my chastity cage. I was about to learn the second most important thing about lord Gregory. Lord Gregory started to ask me questions. Many of them were intended to humiliate me. He started with questions about my crossdressing. Did I like wearing panties? Did I wear panties because my cock was so small? Did I enjoy my submissive house maids role? Did I care Lady Colleen was having sexual relations with other men and even women? Eventually the questions turned to my sexual experiences. Had I ever had sex with a real man or another CD? Had I ever sucked cock? Tasted another sissy's seed? Had I ever been fucked in my sissy hole? I had never thought about some of the questions and when asked if I liked to suck cock I found it almost embarrassing to admit I loved the taste of cock and cum.

Lady Colleen then instructed me to get down on my knees in front of Lord Gregory who stood up. Lady Colleen then informed me that one of my tasks going forward would be to prep Lord Gregory for their love making sessions. He smiled and said I am so please to learn you love the taste of cock and cum. I look forward to letting you taste mine on a regular basis. With that he undid his belt and lowered his pants. I could hardly control myself as Lady Colleen pulled down Lord Gregory's boxers to revel what has to be one of the most spectacular cocks I have ever seen. Flaccid he is about 4 inches long and has a almost perfect girth. As he stood there he made me beg to place his cock in my mouth, beg to taste his cum, beg to be treated like a cheap slut and whore. As I slid his cock into my mouth for the first time I could feel my cock dripping sissy tears into mu panties and I knew I would never have Lady Colleen again. Lord Gregory grew very hard and very quickly he was a full 8 inches. I longed for his cum in my mouth and all over my face but it was not to be that night. When he was ready Lady Colleen took him upstairs and they made love the remainder of the night. Alone and in my cage I went to bed and to sleep dreaming of what almost was.

It was this night that I realized I was and would always be a sissy cuckold.

About 4 years ago now Lady Colleen was out one Friday evening. As usual I was home dressed in a cute outfit with my chastity cage on. I was sipping wine watching TV and thinking about heading to bed when I received a text from Lady Colleen requesting a picture. As always I took a selfie and texted it back. This was not unusual as Lady Colleen would often tell people she met while out of her sissy husband. Most would just let it go but every once in a while curiosity would prompt some to ask questions. This would always lead to Lady Colleen requesting a picture to show them. On this night Lady Colleen did not come home. After work on Saturday we arrived home and routine took over.

For me this means heading to my sissy bedroom and changing into the evenings attire. Always laid out before going to work by Lady Colleen. On this occasion I found a black bra, thong, garter belt and stockings but no dress. A comfortable pair of pumps and my CB 3000. After getting dressed, doing my hair and makeup I went to the living room to find Lady Colleen. There I stood in front of her and put on my chastity cage. Once in place Lady Colleen reached over a snapped the lock closed and placed the keys on a chain around her neck. I so love watching them slide down between her wonderful breasts. Lady Colleen then instructed me to make my dinner while informing me she had a dinner date. She then took a full front photo of me, smiled and said Lord Gregory will think this is cute. (this picture was taken at a later date)


It wasn't until about 10 pm when I next heard from Lady Colleen. Her instructions were clear, be standing at the door ready to receive guests at 10;15. I must have been standing there for 3 or 4 minutes but it felt like hours when the door opened. There stood Lady Colleen and a very handsome young man who was introduced to me as Lord Gregory. He smiled and asked me to turn around. There was a nod of approval and he asked me to lower my panties so he could see my chastity cage. Lady Colleen then informed me that Lord Gregory would be staying the night. As they headed to the living room Lady Colleen gave instructions to open a bottle of wine and serve it. I arrived in the living room to find them on the couch. Lady Colleen explained that they had meet the night before and that Gregory was impressed with my willingness to do as instructed. Lord Gregory then slipped his hand into Lady Colleen's blouse and removed the keys to my chastity cage from between her beautiful breasts. He smiled and asked if I would like him to use the keys to free me. Of course all this was making me drip percum so it was useless to say anything but yes.

Lord Gregory smiled and told me I might be able to earn my way out but that first he wanted to see me in a few different outfits. For each outfit I was sent to my sissy bedroom with instructions on what to put on. This was followed by a walk around the living room to show off the choice. Both Lady Colleen and Lord Gregory took several pictures of each outfit for later use. Here are a couple of the outfits I can remember modeling.


Once they had finished the bottle of wine Lord Gregory informed me that he did not think I had earned the right to have my chastity removed. They just giggled and went to bed.

After a couple of weeks with my first chastity cage Lady Colleen sent me shopping to purchase a CB 3000. A little online research on her part found a local kink shop that carried them in stock. It was early summer of 2015 and I was home alone on my day off. Wearing a ladies tee shirt, shorts and a string bikini panty I headed out thankful not to be required to wear a bra or my chastity cage. I arrived at the shop and was greeted by a nice young lady who was only to happy to help me. Lady Colleen had given me permission to purchase the CB 3000 and if I so desired an anal plug. I had never thought I would enjoy a plug but I spotted a rubber one with a cock and ball ring and I had to give it a try. This picture was taken a few weeks after purchasing the cage and plug. (sorry about the hairy ass)


This chastity cage is when things started to change for us. The original intent of the chastity cage was to stop me from "wanking". Lady Colleen had become increasingly more frustrated with my love making or lack there of due to my tiny and almost perpetually soft cock. Lady Colleen's theory was that if I couldn't wank when alone I would be more likely to perform as desired for her. Unfortunately as many of you know that a sissy is a sissy and we crave what we crave and sex with a woman is just not the turn on a big hard cock is. So while things were better for a while it did not improve things very much. In fact keeping me in chastity was starting to have the opposite of the desired outcome and after a few months Lady Colleen explained to me her frustrations had reached an end. I was given two choices, divorce or allow her to take a lover. Neither solution was on my top ten list of things to do but I had to admit that I was no longer man enough to take care of her physical needs. Thus I reluctantly agreed to allow her to take a lover.

Lady Colleen started leaving me home on Friday and Saturday evening. I would be placed in chastity and dressed in my finest lingerie. On two different occasions I was instructed to take a picture and text her the results. I would later learn that she was showing men she was interested in the photos so that they could get a good laugh at my expense. The second time this happened she brought home her first lover. James was a nice enough guy but he was strictly heterosexual. I had been instructed to greet them at the front door in my French maids uniform. After getting a good laugh they went upstairs to bed and I was sent to the spare room in the basement. This arrangement went on for about 6 months. James would come by, take Lady Colleen to dinner and sometimes they would return and sometimes not. I was always dressed in something and always in chastity. I think however that because James wasn't into sissy Amanda that the relationship was strained and it ended.

Lady Colleen resumed her night out routine. Occasionally requesting a picture but never bringing anyone home. More often then not Lady Colleen would return in the morning. It was clear that she was having sex with others and I gradually began to accept my roll as house maid and sissy. On one evening Lady Colleen had dressed me in just my lingerie. a matching bra, thong panty, garter belt and stockings. At around 10 pm I received a request for a picture. As always I did as requested. A few minutes later I received a request for a picture but was instructed to chose a different matching bra and thong panty. This happened two additional times. At midnight I received instructions to greet Lady Colleen at the door in the red bra and panty set that I had modeled earlier in the evening. This was the set I wore although the picture was taken weeks later.


Much to my surprise when the door opened Lady Colleen was accompanied by a very attractive woman. The woman was introduced as Ashley. She was very sweet and very definitely a lesbian. Ashley was thin, about 5 foot 8 inches, maybe in her mid forties with long blonde hair and piercing blue eyes. Both of them just laughed as they walked in and Lady Colleen just smiled and said I told you he does as he is told. For the next hour or so they sipped wine and picked out outfits for me to model. Short sheer nighties then matching bra and panty sets then a real laugh as I pranced around in my maids uniform. My panties have never been so wet. Finally Lady colleen called me to stand in front of her. As I did she lifted my dress and petticoat. It was clear that I was excited by the rather large wet spot in the thong I had on.

Lady Colleen then did something she had never done before. She removed the key to my chastity cage from the chain around her neck and removed my chastity cage. With a giggle she said watch Ashley this is why I take lovers. Lady Colleen then began to rube my pathetic soft freshly shaved cock between her two fingers. My precum made the head slide easily between her fingers. It took all of 30 seconds for me to explode all over Lady Colleen's cleavage. Ashely just snickered and said she had never witnessed a man climax without getting an erection. I was then directed to lick Lady Colleen's chest clean of my cum and I was placed back into chastity. Lady Colleen and Ashley then went to bed leaving me to sleep in the spare basement bedroom. Lady Colleen who is bisexual has continued to sleep with Ashely on occasion but they have never taken the time to humiliate me in this manner again.

After a couple of years of consulting work Lady Colleen and I managed to purchase business. This business is seasonal and for the first year it took up most of our time. About 6 years ago we had grown the business to the point that we each were able to get a day off. A very familiar routine once again a rose and I would look forward to my day off and the chance to dress, even if it meant a day of chores around the house. It was during one of these days off that Lady Colleen caught me "wanking" as she calls it. I was dressed in my new French Maids Uniform cleaning the home. After folding the laundry I was so horny that I went to the bathroom, lifted my dress and petticoat and climaxed into the sink. When Lady Colleen arrived home she called me to the living room. There she instructed me to stand in front of her for an inspection. Inspections were and are common. They are meant to ensure I do not change out of the approved outfit of the day. On this day however it lead to me being caught with my hand in my panties as it was very obvious from the dried spunk on my panties that I had not gotten all of my cum in the sink. With a very matter of fact voice Lady Colleen asked if I had wanked during the day without her permission. I was caught and I knew it, I was left with only one option and that was to admit to what I had done.


It took a couple of weeks but this incident lead to Lady Colleen purchasing me my very first chastity cage. When I arrived home from work on her day off she called me to the living room. She announced with a big smile on her face that she had purchased me a gift. This had always meant some pretty lingerie and In immediately felt a tingle in my panties (yes by this time I was wearing panties 24/7/365). When I opened the gift I was surprised to see the chastity cage. Lady Collen just looked at me and said come on let's see how it fits. Putting on the chastity cage for the first time was a learning experience for both of us. Painful for me as I got pinched in all the wrong places several times. Once in place Lady Collen told me that from this point forward I would be required to wear a chastity cage when ever I was home alone. True to her word she started locking me away before going to work on my day off. I have now been locked in chastity whenever I am home alone for the past 5 years.


This chastity cage would not last long as it cut me several times and was much more difficult to put on than Lady Colleen wanted.

Lady Colleen and I have been together almost 20 years ago. I had been going out with other crossdressers to various support group events. Typically that involved a rubber chicken dinner and a couple of days of dressing at an out of town hotel. We would also get together at each others home for dinner drinks but everything was strictly social. No sex as many of us were still hoping to meet that special woman who would except us for who we were. After a few years a male/crossdresser and genetic female came to me and told me of a woman they had meet on a double date a few weeks back. The person she was with was also trans and they were going their separate ways. They said why not meet her she is bi-sexual and excepting of crossdressing men. I agreed on the condition that she was told before hand that I was a crossdresser. I had grown fond of dressing and I didn't want to hide it from anyone I was dating. All agreed and we met for dinner. A few weeks later we got together for dinner at my apartment and we started dating.

Our third date was an overnight stay for a social event out of town. The event was put on by the group I belonged to and was the vehicle by which I had met the couple who introduced us. Upon arriving at the room checking in and getting settled Lady Colleen (then just Colleen) handed me a wrapped gift. I was very surprised by this and frankly feeling a little overwhelmed but I opened it to find a short teal silk chemise nightie. Oh my I couldn't help it I broke down into tears. No-one had ever bought Amanda anything never mid a real woman. Needless to say I wore it to bed that night and made love to Lady Colleen in it the next morning.

Colleen and I continued to date for several years. We went out socially with friends and had what others outside of our circle of crossdressing friends saw as a normal male female relationship. I was in heaven as I could dress when ever I wanted and I slept in a nightie every night. I wore the teal one out and was a little sad when I finally had to get rid of it. We had and still do have a full regular life were no one knows of Amanda. After a few years of dating we purchased a home and moved into together. After a few more years we got married. I am sure some are hoping to hear about kinky sex but for us it was and still is normal for both of us to wear a silky nightie to bed and have very plain regular sex in the am.

As we have aged things have changed between us. Although we are still committed to our marriage and neither of us would change that my ability to satisfy Colleen has ended. We still have sex but it is not as frequent or as good as it was in the beginning. I don't get as erect as I used to and this results in difficulties having penetrating sex. Leaving Colleen unsatisfied. In late 2012 I lost my job and was out of work. I did various odd jobs but was older and could not find a suitable position (pay wise). I spent many days at home which was great for Amanda but it put a lot of stress on our marriage,. Colleen would get up and leave for work at a job she hated and I would stay home all day dressing as Amanda. I would take pictures and post them to Flickr. I would chat on Yahoo chat (god I miss the chat rooms on Yahoo) and when I was good and ready I would cum and change back to boy mode. I would spend the afternoon looking for work sending out resumes and applying for jobs online.

One afternoon after cumming on cam in a chat room I got up to get changed. While taking a shower Colleen came home from work early. In the shower I didn't even notice she had come home. I dried off and headed to the bedroom to get dressed when I heard her crying in front of my computer. I was devastated as I was sure this would be the straw that broke the camels back and I would be single again. As I walked in there I was on the computer. A picture of me in my garter belt stocking bra and panties, hair and makeup done. She looked at me and told me what a fool I was. How did I expect to get a job if people saw the pictures. Even worse, if I was goofing around taking pictures and posting them on line I was not looking for a job which we needed financially. She got up and left the house. I was sure she would never return. I don't know but I think she spent the night at her mother's house.

The next day Colleen came home from work and sat me down at my computer. She made me open every page for every group I belonged to. She wrote down web addresses user id's and passwords. She then sent me to the guests bedroom with instructions to remain there for the remainder of the evening. When Colleen got up in the AM she told me she would leave me forever if I posted another picture. I was to spend the day in boy mode and start to search for a real job or else. I did as instructed and it was the last we spoke of the incident for a few weeks. Eventually she calmed down and told me her true feelings. She felt betrayed as she had always let me dress. She had never restricted my dressing activities and to find out what I was doing behind her back hurt her deeply. That was 8 years ago and I am sure she is still not completely over it.

After a month or so Colleen began leaving out outfits for me to wear during the day. I had to be in the exact outfit when she arrived home from work, the house had to be clean. the laundry done. and dinner needed to be ready. After dinner I had to produce proof that I had applied to a minimum of 5 jobs and called to follow up on any leads generated. My life became very regimented and I began to serve more as the house maid than a husband. I was and still am ok with that as I was the one who made the error and I need to do whatever I can to make it right. Ultimately my job search failed. In the end we purchased a seasonal business that gives us a great deal of freedom in the summer but keeps us very busy in the winter. This incident changed our relationship. It has progressed in ways that I never thought it would when we first met. More on the current state of things next time.

After living on my own for a few years I began to explore the world outside of my apartment. I found a support group for cross-dresses and I went to my first public event. I had never been out dressed as a girl and I was scared to death to step out the door of the hotel room. It was a simple dinner at the hotel and I remember that as I sat down a very attractive post op girl looked at me and asked me my name. When I said Amanda she just quipped back I know your A - Man - Da but what is your name. I was devastated as my confidence was non-existent. I recovered and spent the evening talking to other cross-dressers for the very first time in my life. I became very social in this group getting together for the monthly events and making friends and eventually joining these friends socially as Amanda. Surprisingly this group of friends never lead to any sexual encounters but it did give me the confidence to start looking.

One of the groups this lead to was a social group run by two dom females. They held a monthly "meeting" in the basement playroom of a home nearby. It was BYOB and you had to get dressed when you arrived. Several times I shared a bedroom with another CD getting dressed. These meeting where a lot of fun. Once everyone was there the two dom woman would start to play. Lady Star would make you stand in front of her while she lifted your skirt. She would caress you and make you hard while everyone watched. This lead to several very horny CD's willing to do whatever they were told. Sometimes they would make us suck each others cocks or jerk each other off. After a couple hours of teasing and playing they would make each of us strip down to our lingerie and they would masturbate us until we climaxed. They were some of the best organisms I ever had.

My experimentation lead me to the classified / personal ads. Yes I know I am dating myself but it was before the Craigslist. There I met a woman from a neighboring city. We agreed to meet the first time for dinner and a second time to attend a private party. I drove to a local mall and finished getting dressed in the back of her mini van. From there we walked into the party. Once upstairs we walked around until she had a comfortable spot to sit. She had me stand in front of her so she could get "a good look" at me. She lifted my skirt to find my black satin thing, garter belt and stockings . All in front of a room full of people to see. She very gentle began to caress my cock through my panties. After a few minutes she pulled my thong down to reveal my freshly shaved cock semi hard and dripping gallons of precum. She continued to caress my cock until it was stiff as a board. When she was ready she lowered my skirt making me look ridiculous. Standing there my hard cock causing my skirt to tent out it was clear to everyone that I had an erection. This was humiliating to stand there as people looked on and she giggled.

After a few minutes of this she made me follow her into an adjacent room. There she made me kneel down in front of a small bench. As I knelt down she pushed my head forward so that I was lying on the bench. She lifted my skirt to expose my bare bottom and loudly proclaimed that no sissy of her's would walk around with a hard little sissy cock. It was at this point that I felt the first strike from her paddle. I winced but said nothing. The second blow fell. This one a little harder. She then began asking me questions designed to humiliate me. Did I wear panties because I had a small cock? Did I like wearing panties? How long had I been a sissy? Would I like to suck another sissies little cock? With each answer came a strike from her paddle. If she thought I wasn't being truthful she would strike me harder. This went on for 20 or 30 minutes. When she was done she told me to stand up. As I did my panties feel around my ankles and I looked up to see 25 or 30 people just watching the whole thing. Humiliated I bent down and pulled my panties up. We then spent the rest of the night socializing with people. She eventually put a collar and leash on me and lead me around offering my services as a foot message slave to all the women at the party. Some took her up most didn't. After we left I got into my car dressed and so horny I jerked off in the car on the ride home.

The social group also lead to meeting several crossdressers who have become life long friends. One of these people introduced me to my wife. Yes she know all about Amanda as I wouldn't go on the blind date unless she was told. More on that next time.