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Sissy Dreams

"Crossdresser hubby."

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The meal was simple, just the main dish, desert and coffee. As the women lingered over their coffee I began to quickly eat my meal. I had just managed to finish when I heard Jenifer call, “Mitsy.”

When I entered, she said, “We have decided to have our coffee in the living room. Top up our cups with fresh and bring them to us.”

I started to collect the cups when she asked, “Did you hear me, Mitsy?”

I knew what she wanted so I answered, “Yes, Miss Jenifer, I will bring fresh coffees to the living room.”

Terry couldn’t contain herself any longer and laughed out loud as she said, “Miss Jenifer! Oh, that’s precious.”

Of course I felt myself blushing again as the women walked into the other room. I retreated to the kitchen, refilled the cups with fresh coffee and using a tray carried it into the living room. With my tight corset I had to bend my knees in order to place the cups in front of them. Jenifer said, “Go clean up the kitchen and then come back to see if we want anything else.”

I said, “Yes Miss Jenifer,” and went to clean up. When I finished I returned to the living room and waited silently while they chatted. At some point Terry turned to me and said, “You make a very presentable woman Mitsy. I don’t think I would have recognized you if Jenifer hadn’t told me. I just wish I had a camera handy to record this for posterity.”

Jenifer said brightly, “What a good idea. Mitsy go up to our room and open the larger suitcase. The camera is in the right-hand pocket. Go and fetch it.”

When I came down, they took pictures of me both full length and close up. Then they had me take pictures of them sitting together on the couch. Terry brought a couple of books and set them on the table. Pulling the table back, she set the camera on the books. Then she had me pose kneeling in front of them, and with the timer, she took a shot with all three of us. They liked the idea so much they moved the camera and books to a different table and had me pose bending my knees with their cups on a tray, as if I were serving them. They thought the entire process of posing and picture-taking was great fun.

When they finished taking pictures, Terry asked, “Mitsy, do you like cross dressing?”

I replied, “No, Terry, I don’t.”

Jenifer interrupted and said, “Mitsy, while we are guests in Terry’s home you should treat her with the same respect you treat me and refer to her as Miss Terry. Do you understand?”

“Yes, Miss Jenifer. No, Miss Terry, I don’t enjoy wearing women’s clothes and makeup.”

“Then why do you do it?” asked Terry.

“I do it because I love Miss Jenifer and she told me to.”

Turning to Jenifer, Terry asked, “Do you usually keep him in drag?”

Jenifer smiled and said, “No. Usually he is naked at home. Well naked except for his chastity belt, butt plug and slippers.”

“Ooh, I’d like to see that. Besides, this is a vacation week for both of you and you ought to be able to be yourselves and relax.”

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Jenifer turned to me and said, “Go upstairs and get undressed. Come back in what you normally wear at home.”

I blushed and thought of arguing but I didn’t want her to extend my week of chastity and knew that I had better obey, no matter how humiliating it would be. In the end I simply said, “Yes Miss Jenifer.”

When I came back down, nude except for the chastity belt and the fuzzy pink high heeled slippers Terry couldn’t control her laughter. I was also wearing the butt plug but it was so deep within me that it was almost invisible. Jenifer ordered me to stand in with my legs apart and my hands behind my head. Of course this set off another round of picture taking.

Terry wanted to see the chastity belt so Jenifer had me stand in front of her in the same pose that I had been in. Janet was explaining about the four digit combination lock and how the combination could be reset each time the lock closed when Terry reached out and tugged the curved tube. She then ran her hand, palm up, between my legs and cupped my testicles. After a week of sexual frustration by Jenifer, Terry’s touch caused me to moan. She immediately jerked her hand back and said, “I’m sorry Roger. Did I hurt you?”

I noted that I was back to Roger and no longer Mitsy as I replied, “No Miss Terry. It’s just that it has been a long time since I have been allowed to cum and things are very sensitive.”

Terry turned to Jenifer and asked, “How often do you let him cum?”

Jenifer said, “Almost every day when he’s been good but he was being punished this week and hasn’t cum since last Saturday. Today’s the last day of his punishment and if he is obedient I might let him cum tomorrow.”

Terry said, “That doesn’t seem very nice. After all this is his vacation and I’m sure he would enjoy it more if we let him cum.”

Jenifer thought for a minute and then, with a twinkle in her eye she asked me, “Would you like to show Terry how you masturbate?

I realized she was talking about me masturbating in front of them. Here I was nude in front of two fully clothed women and she was asking if I wanted to humiliate myself further by jacking off in front of them. At the same time I was very frustrated and both Terry’s touch and the situation had made me very needy.

I was desperate to cum so I answered, “Yes, Miss Jenifer.”

Terry asked, “Do we need a towel or something? I don’t want his stuff all over my rug.”

Jenifer’s answer made it clear just how humiliating she planned to make this. He said, “We don’t need a towel. We can just use a glass. A drinking glass will do very nicely.”

Terry must have realized what Jenifer planned because as she stood to go to the kitchen and blushed as she said, “Oh my!”

Jenifer said to Terry, “Come sit here on the couch next to me so that we can both watch together.”

Then she turned to me and said, “Roger, take these coffee cups into the kitchen and bring back a drinking glass. Make certain it is big enough to catch your ejaculate but small enough so that after you ******* your semen you can get your tongue all the way to the bottom to lick the glass clean."

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Written by DominatrixMoore
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