I apologize for not posting for so long. Mistress informs me that I will have to catch up. They have sent me out many times but fortunately I have not had to blog about them. But that will change.
Today I experienced one my potentially most embarrassing outings ever. Normally when they send me out as a sissy it is away from home but today they decided to do it here. It was time for me to cut the grass, or mostly the weeds, which had gotten rather high due to recent wet weather. I had on bright pink bra and panties. They let me put a pair of white shorts and a white blouse on. The pink undergarments were noticeable if you looked closely but a passerby would not notice. I did not have to wear my breast forms so only my natural 44B breasts were visible not my 44DDs. Just after I started it started misting. By the time I was half done the sidewalk was entirely wet. I went in and asked if I could stop. Since the forecast is for a couple of wet days they said that the yarded needed to be done and I should finish. I went back out and continued as it misted more heavily. I was getting soaked. We live on a corner and the side street is fairly busy with traffic and joggers, dog the walkers and mothers pushing strollers regularly go by. I was still mowing when I heard a car stop next to me and a young lady yell out, “I love your pink” and then drive off. I looked down and the rain had made the blouse and shorts translucent and you could clearly see the pink. I was so embarrassed. Many people had gone by and I did not notice anyone I knew but I also wasn’t really paying attention. I ran thru the last pass with the more and was in tears by the time I got the mower back in the back yard and the gate closed. After I put the mower away I went inside. Cindy said, “Now that wasn’t too bad. You finished before it really started to rain.” I had to tell them about the comments from the lady. They looked at me and Alicia said, “Oh my, I can clearly read the Call Me on the back of your panties. I hope no one else saw that and calls you” with a hearty laugh. I really hope that no one that knows me drove by after I was wet.
Monday, September 17, 2012
Thursday, April 1, 2010
Another adventure
Mistress sent me out on the most humiliating days I have had yet. First she had me put on a temporary tattoo on my arm that said "sex slave". Then i was dressed in a short schoolgirl skirt, see thru pink blouse, black stockings, garter belt, black flats, two sissy anklet, my pink dog collar with sissy heart dog tags, pink 46DDD bra with breast forms.
The skirt barely covered my stocking tops. She first sent me to Walgreen’s to buy tampons and rubbing alcohol so that I could remove the tattoo.
As I got out of the car, dressed as an obvious sissified male, totally male head, a clerk came out of the store I guess just to look around. She saw me and just started smiling. She was about 25 and very attractive little woman. She stood at the door as I walked in with a big grin on her face and asked if she could help me. I told her I needed rubbing alcohol and she told me where it was. I went to the back of the store and picked up the alcohol and then to the feminine products section where I picked up regular and super plus tampons and went to check out. The same clerk was at the check out. I was third in line behind two women. The clerk kept looking at me and smiling. It was finally my turn and she asked me if I knew I had two sizes of tampons and I had to tell her that the regular were for mistress and the super plus were for me. She laughed and said, "Oh I see". She then noticed the tattoo and said it was pretty as were my pink nails with the French tips.
I could not wait to get out of that store. My next stop was Dots where I tried on several dresses. With the new boobs that I now wear (46DDD) none of the dresses would fit over them properly so I did not have to buy a dress.
Then I had to go to the Hustler Gentlemen’s Club and visited the video arcade. I went into the room where they were showing relatively hardcore movies. They were several men there and I became the center of attention.
I sat on a couch and two men sat on either side of me and they began feel me up. They pull my skirt up and were rubbing my ruffled sissy panties. They kept trying to feel my sissy clit but it is so small and was covered with very thick maxi pad.
They each took one of my hands and placed it on their member and I had to stroke them. I then felt two hands on my boobs and looked up to see two men behind me stroking themselves as they groped by boobs. My arms got very tired as I stroked the men next to me but neither one got very hard but they did ooze precum. One of the men behind me dribbled down my shoulder onto my breast. The other one tried to force my head to turn to suck him. I told him I was not allowed to suck anyone with out a condom. He asked if I had one and I got one out of my little Princess pink purse. He put it on and moved around to the front of the couch in front of me. The two men on either side pulled me up over the couch so that I could suck the other man. In doing so they bent me over the back of the couch. They pulled my skirt completely off and proceeded to grope my ass. When one of the girls on the screen started spanking the other one, they got the same idea and started spanking me. Both my ass and my thighs and occasionally underneath on my sissy clit. They must have spanked me 100 times. My bottom was very sore. I was unable to get the other man to cum. Eventually he just ripped off the condom and started stroking himself. The other two sat me back down on the couch and it hurt to sit. The third man came around and continued to stroke himself until he shot all over both of my breasts. He then put himself away picked up my skirt and walked out. He took the skirt out into the adult boutique and threw it into the corner. I followed him in with my black stockings, garter belt and pink ruffled sissy panties fully exposed with wet cum stains on my blouse covering my shoulder and boobs. The two clerks laughed as I picked up my skirt and put it on before leaving. I have never been so humiliated in my life.
Tuesday, July 14, 2009
New adventure
I left here wearing pink bra, breast forms, pink stockings, black garter belt, pink ruffled sissy panties, two sissy anklets, corset, Barbie watch, 3 sissy bracelets, a man's shirt tucked into the panties, and khakis with black flats.
My first stop was McDonalds where I ordered a sandwich and drink and then sat at table where I had to put on my pink leather dog collar with 3 sissy hearts and long press-on nails with pink tips. Fortunately no one seemed to notice.
Next stop was Lane Bryant at South County mall. The clerk remembered me and said that you have not been here in a while. I told her that mistress had not sent me recently. She just smiled. I told her I needed a new short dress or skirt and it could not be any longer than knee length. She could only find one to try and it ended up being to small and too long. I then when out to the car where I had to change into the short dress I bought a couple of month ago at Dots. I it barely covers the stocking tops. I stopped at For Lovers Only, an adult lingerie and novelty store, and had to purchase my first butt plug. I bought a medium size butt plug that was 5 inches long and 1.75 inches in diameter at its widest point and put it in my pink clutch purse that I was carrying.
My first stop was McDonalds where I ordered a sandwich and drink and then sat at table where I had to put on my pink leather dog collar with 3 sissy hearts and long press-on nails with pink tips. Fortunately no one seemed to notice.
Next stop was Lane Bryant at South County mall. The clerk remembered me and said that you have not been here in a while. I told her that mistress had not sent me recently. She just smiled. I told her I needed a new short dress or skirt and it could not be any longer than knee length. She could only find one to try and it ended up being to small and too long. I then when out to the car where I had to change into the short dress I bought a couple of month ago at Dots. I it barely covers the stocking tops. I stopped at For Lovers Only, an adult lingerie and novelty store, and had to purchase my first butt plug. I bought a medium size butt plug that was 5 inches long and 1.75 inches in diameter at its widest point and put it in my pink clutch purse that I was carrying.
The next stop was the Dots store that I have had to go to the last couple of times. I had to get a dress or skirt. Mistress was still angry that I did not come home with a dress when she sent me 10 days ago. The lining of the only short plus size dress they had then was several inches shorter than the thin dress and my stocking tops and garters were very obvious. When I got home, she said she did not care. This time I knew I had better come home with something whe
ther it was appropriate or not. I looked at the clearance plus size garments and did not find the dress anymore. All three clerks offered to help me. Two of them started looking for dresses that were knee length or less. They found two possible dresses. I went to try them on. When I first entered the dressing room, I took my dress off, pulled my panties down and had to sit on the butt plug to insert it into my sissy pussy. It was the first time anything but the tampons I wear during my monthly period had been in my sissy pussy. It was very uncomfortable. I pulled the sissy panties up and tried on the two dresses. One, a white one, looked awful on me but the flowery one did not look too bad and was clearly above the knees but if I was careful covered the stocking tops. The lining if pulled down properly was only a couple of inches from the bottom of the dress. The garters and stocking tops although noticeable if one was looking did not stand out like in the dress I did not buy last time.
I came out of the dressing room wearing the flowery dress and walking a little different due to the butt plug in my sissy pussy. I asked the clerk if I could pay for and wear the dress out of the store. She got a pair of scissors and cut off the tag and left it on the counter for the other clerk. The other clerk was checking out another customer, a very attractive blonde woman. She helped her and asked her to sample several perfumes. It took several minutes and the blonde kept looking my way and smiled. Finally she finished with that sale and s
tarted on mine. She said, I don’t suppose you want to sample the perfumes, do you?” I told her not this time. As I was paying for the dress the clerk said, “That pink necklace matches your dress.” I thanked her and told her that mistress says I have to always wear it when I am out so that everyone knows my status.
I then went next door to Payless Shoes where they have been very nice before. A clerk who helped me last time came over and welcomed me and asked to help. She looked at my heels and said that they were her favorite shoes. I told her that they were mine also and that I had bought them there a year ago. She pointed out the 11W and 12W shoes and left me to look around. The other two younger clerks, in their 20s, came by and offered to help. They both seemed to stare but were very helpful. One spent some time admiring my collar and asked about the tags. I told her that mistress got them for me. She said it was very nice. She had me sit as she tried two pairs of shoes on me. She noticed and commented on the lacy tops of my pink stockings. It was uncomfortable sitting on the hard stool with the butt plug in place. Unfortunately, they did not having any pink shoes which is what mistress wants me to get. She did offer that they received shipments on Tuesday and Thursdays and that I should come back and check in.
ther it was appropriate or not. I looked at the clearance plus size garments and did not find the dress anymore. All three clerks offered to help me. Two of them started looking for dresses that were knee length or less. They found two possible dresses. I went to try them on. When I first entered the dressing room, I took my dress off, pulled my panties down and had to sit on the butt plug to insert it into my sissy pussy. It was the first time anything but the tampons I wear during my monthly period had been in my sissy pussy. It was very uncomfortable. I pulled the sissy panties up and tried on the two dresses. One, a white one, looked awful on me but the flowery one did not look too bad and was clearly above the knees but if I was careful covered the stocking tops. The lining if pulled down properly was only a couple of inches from the bottom of the dress. The garters and stocking tops although noticeable if one was looking did not stand out like in the dress I did not buy last time.I came out of the dressing room wearing the flowery dress and walking a little different due to the butt plug in my sissy pussy. I asked the clerk if I could pay for and wear the dress out of the store. She got a pair of scissors and cut off the tag and left it on the counter for the other clerk. The other clerk was checking out another customer, a very attractive blonde woman. She helped her and asked her to sample several perfumes. It took several minutes and the blonde kept looking my way and smiled. Finally she finished with that sale and s
tarted on mine. She said, I don’t suppose you want to sample the perfumes, do you?” I told her not this time. As I was paying for the dress the clerk said, “That pink necklace matches your dress.” I thanked her and told her that mistress says I have to always wear it when I am out so that everyone knows my status.I then went next door to Payless Shoes where they have been very nice before. A clerk who helped me last time came over and welcomed me and asked to help. She looked at my heels and said that they were her favorite shoes. I told her that they were mine also and that I had bought them there a year ago. She pointed out the 11W and 12W shoes and left me to look around. The other two younger clerks, in their 20s, came by and offered to help. They both seemed to stare but were very helpful. One spent some time admiring my collar and asked about the tags. I told her that mistress got them for me. She said it was very nice. She had me sit as she tried two pairs of shoes on me. She noticed and commented on the lacy tops of my pink stockings. It was uncomfortable sitting on the hard stool with the butt plug in place. Unfortunately, they did not having any pink shoes which is what mistress wants me to get. She did offer that they received shipments on Tuesday and Thursdays and that I should come back and check in.
Wednesday, June 10, 2009
Shopping Trip
Mistress sent me out on another shopping adventure again last Thursday. I was wearing the usual pink ruffled sissy, black garter belt, black stockings, sissy anklets, corset, pink bra, and breastforms. I wore Mary Jane’s with 3 inch heels, thin white crop pants, pink peasant top, pink dog collar with sissy dog tags, pink press-on nails, and a pink Barbie watch. You can easily see the pink panties and black garter belt and stockings thru the top and pants.
I was sent to a Dot’s store in Maplewood. It was the first time I had been there. Mistress had been in and had seen a thin frilly pink top and a couple of flowery short dresses that she wanted me to buy.
The two clerks were not very friendly. They seemed to ignore me but offered to help others. When I asked for help with finding a size they did help and when I had pick out 2 dresses and the pink top to try on, one of the did become helpful. She led me to the dressing room and after she opened the dressing room door, she looked closely at my neck and asked what the necklace said. I had to explain that it was a dog collar that mistress made me wear and that the tags said, “Owned by Diane”, “Diane’s Sissy”, and “Wendesis”. I told her that was my name. She just responded “Oh.” The top fit fine but the dresses, although very cute, were two sizes smaller than I usually wear and as a result too short. They did not cover my stocking tops at all. I purchased the top and asked if I could change into it to wear. I put it back on and the clerk help remove the tags for me. I left the store and went to the car where I removed the pants and put on a short black skirt. Here are pictures of the new sissy top and my stocking top and pink nails.
I then drove thru McDonalds with my skirt pulled up and purchased a soda.
It was then across the river to the Hustler Club. I went into Boutique/Video Arcade and bought a wristband to go into the arcade to watch videos in the booths. I walked around for a few minutes before I walked into a booth. Mistress had told me to leave the door ajar for at least ten seconds before I closed it. I watched a shemale video and then left the booth to walk around again. There were about 10 men wandering around but thankfully none seemed interested in me. After watching another video, I left and drove to Wiseguys Gentlemens Club.
When I walked in there seemed to be more dancers than men. Several of the ladies said hi to me and Autumn came rushing over and gave me a big hug and kiss. She said she had had a bad day and seeing me really cheered her up. We went to the bar and bought me a Shirley Temple and she got a shot. We then went and at a table and talked, held hands and rubbed legs. She is always so nice to me. At 1:30, I had to excuse myself and tell her that it was time for me to change my tampon. It had been four hours and I am not allowed to miss by more than 10 minutes. I went into the men’s room and changed my tampon and returned to Autumn. She suggested a private dance. I asked how much and she said $30. I only had $25 left and she said she would do it for me. We went into the backroom and she gave me a private although she never really touched my crotch and I did leave very unsatisfied. Next time I am sent there, I will tell her that if she is not going to help me cum, then I would rather tip her to just sit and talk for a long time rather than have a one song private with little stimulation.
When I returned home, Mistress Diane, Alicia, and Cindy were there. I do to describe in detail the entire trip while I was masturbating for them. After I came I had to clean up the mess with my tongue while continuing to stroke for 20 more minutes. They just laughed at my futile efforts to get my "little sissy clit" hard again.
I was sent to a Dot’s store in Maplewood. It was the first time I had been there. Mistress had been in and had seen a thin frilly pink top and a couple of flowery short dresses that she wanted me to buy.The two clerks were not very friendly. They seemed to ignore me but offered to help others. When I asked for help with finding a size they did help and when I had pick out 2 dresses and the pink top to try on, one of the did become helpful. She led me to the dressing room and after she opened the dressing room door, she looked closely at my neck and asked what the necklace said. I had to explain that it was a dog collar that mistress made me wear and that the tags said, “Owned by Diane”, “Diane’s Sissy”, and “Wendesis”. I told her that was my name. She just responded “Oh.” The top fit fine but the dresses, although very cute, were two sizes smaller than I usually wear and as a result too short. They did not cover my stocking tops at all. I purchased the top and asked if I could change into it to wear. I put it back on and the clerk help remove the tags for me. I left the store and went to the car where I removed the pants and put on a short black skirt. Here are pictures of the new sissy top and my stocking top and pink nails.
I then drove thru McDonalds with my skirt pulled up and purchased a soda.
It was then across the river to the Hustler Club. I went into Boutique/Video Arcade and bought a wristband to go into the arcade to watch videos in the booths. I walked around for a few minutes before I walked into a booth. Mistress had told me to leave the door ajar for at least ten seconds before I closed it. I watched a shemale video and then left the booth to walk around again. There were about 10 men wandering around but thankfully none seemed interested in me. After watching another video, I left and drove to Wiseguys Gentlemens Club.
When I walked in there seemed to be more dancers than men. Several of the ladies said hi to me and Autumn came rushing over and gave me a big hug and kiss. She said she had had a bad day and seeing me really cheered her up. We went to the bar and bought me a Shirley Temple and she got a shot. We then went and at a table and talked, held hands and rubbed legs. She is always so nice to me. At 1:30, I had to excuse myself and tell her that it was time for me to change my tampon. It had been four hours and I am not allowed to miss by more than 10 minutes. I went into the men’s room and changed my tampon and returned to Autumn. She suggested a private dance. I asked how much and she said $30. I only had $25 left and she said she would do it for me. We went into the backroom and she gave me a private although she never really touched my crotch and I did leave very unsatisfied. Next time I am sent there, I will tell her that if she is not going to help me cum, then I would rather tip her to just sit and talk for a long time rather than have a one song private with little stimulation.
When I returned home, Mistress Diane, Alicia, and Cindy were there. I do to describe in detail the entire trip while I was masturbating for them. After I came I had to clean up the mess with my tongue while continuing to stroke for 20 more minutes. They just laughed at my futile efforts to get my "little sissy clit" hard again.
Friday, December 26, 2008
Dog Collar
Mistress brought home a pink dog collar with pink sissy dog tags for me to wear from now on whenever she sends me out. Here are a couple of pictures. I am not looking forward to being seen in public wearing this but I will have no choice.
Monday, December 15, 2008
Friday, December 12, 2008
Tuesday Mistress Diane sent me out on another adventure. As I was dressing, she took pictures of what I would be wearing as I made my rounds. I started with white lacy garter panties and a kotex pad to keep my sissy clit from staining my panties, a black garter belt, hot pink fishnet stockings, and pink ruffled sissy panties.
I also had on a rubber corset and pink bra with breast forms,
two sissy anklets and 3in black heels.
I left the house wearing a short dress, Barbie watch and three pink sissy bracelets and carrying my pink clutch purse. 
I was also wearing press-on nails with french tips. 
My first stop was For Lovers Only, an lingerie and adult novelty store. I had to ask for clear bra straps as the pink bra straps showed with the thin spaghetti straps of the dress. They did not have nay but suggested that I go to K-mart. My next stop was the Dots store at Telegraph and 255. The dress I was wearing came from a previous trip to a different Dots store. I was supposed to purchase a new outfit. The clerk had they had no dresses on sale and she could only find one skirt. I had to try it on but it did not fit well. Before I left, I asked if they had clear bra straps but they did not. I then went next door to Payless Shoes to look for pink shoes. The clerk asked if she could help and I said I just needed pink shoes. She said they had no pink ones in stock in my size and kept showing me other that she said would look good with my outfit. I left without purchasing anything.
I then had to take off my dress in the car and put on a pink peasant top. As I sat in the car my garters, stocking tops, and sissy panties were very obvious. I had to drive thru Dairy Queen and ordered a soda. After the clerk took my money, she left the window and went and talked to another clerk who came over to the window with her and stuck her head out looked closely at me and said, “Nice outfit”. The first clerk handed me my soda and change and said, "Have a pretty day”.
I then drove across the river to the Hustler Club. Before getting out of the car, I put my short black skirt on which barely covered the stocking tops and garters.
I then had to take off my dress in the car and put on a pink peasant top. As I sat in the car my garters, stocking tops, and sissy panties were very obvious. I had to drive thru Dairy Queen and ordered a soda. After the clerk took my money, she left the window and went and talked to another clerk who came over to the window with her and stuck her head out looked closely at me and said, “Nice outfit”. The first clerk handed me my soda and change and said, "Have a pretty day”.
I then drove across the river to the Hustler Club. Before getting out of the car, I put my short black skirt on which barely covered the stocking tops and garters.
I went into Boutique/Video Arcade and bought a wristband to go into the arcade to watch videos in the booths. I walked around for a few minutes before I walked into a booth. Mistress had told me to leave the door ajar for at least ten seconds before I closed it. As I was reaching to close it, opened and a man asked to come in. Once in side, I put money in the video machine and we started watching a shemale video. He asked me to pull up my skirt and I did and tucked it into the waistband. He did the same with the back of the skirt and then he started rubbing my bottom. He then unzipped his pants and took my hand and placed it on his member. I very reluctantly stroked him until he shot. He wiped himself on my skirt, quickly zipped his pants and left. I stood there sort of stunned. After a few minutes I regained most of my composure and left. As I walked back into the boutique, I heard one of the dancers that I passed say, “look at those sissy panties”. I then realized that my skirt was still pulled up in back revealing everything. I left and ran to the car as quickly as I could.
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