A Toy Party Story

Toy Party Story

Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him.

He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held much responsibility and control. He explained to me that giving himself to me completely would be the ultimate turnon for him, and that doing it dressed as a woman would excite him in a way that he rarely experienced with vanilla sex.

He wanted to give himself to me to be used like a toy. I thought that was really ironic, because I was going to have a toy party, and I thought that it might be kind of fun to have a living breathing sex toy to wait on the people at my party and liven up things a bit.

I thought a lot about who I might invite that would make the sex toy party even more than he had envisioned or planned for. I invited several bisexual friends who were in their 30s and 40s. I also invited one young hunk who was 25 years old who I knew to be very bi curious.

My friend, of course, was pretty nervous about the party. He asked me a couple of times on the phone what he should wear to the party. I finally decided that it would be prudent to take him on a shopping trip to find exactly the right clothes for him.

I also thought that it would be fun to embarrass him in the women's department. I wanted his face to be several shades of pink as I picked out panties, stockings, and bras for him. I also planned on asking the sales woman if she had a measuring tape so I could measure him in the store to figure out what bra to buy.

The day of the shopping and the party came, and I met him to go to the store. I could tell right away that he was both aroused and nervous.

I whispered naughtily to him that I hoped that he hadn't been masturbating or touching himself in anticipation. He blushed and said that actually he had. I told him that he was a very naughty sub and that he would definitely have to be punished. I told him that I was going to pull up his skirt and spank his naughty ass at the party tonight in front of everyone. He said that he would do whatever it took to please me.

At the Store

In the store, I knew exactly what I wanted and made directly for the women's department. My friend was not keeping up and I kind of guessed it was because he was nervous and anxious about what I might say.

Although I understood the nervousness and where it was coming from, I was there to accomplish a task and I wasn't in the mood to coddle him. It was at moments like that I really wished for a collar and a leash. I made do though and grabbed his hand and pulled him along like a pouting child.

I told him that if he wanted a treat after our shopping trip that he had to behave like a good boy. There were other people shopping nearby who smiled and probably were thinking, "what a cuckold?". But that sufficiently embarrassed him so that he quit lagging and kept up.

In the women's department, I headed for the lingerie section. I have to explain here that I like black panties because they are always so sexy and excite me immensely.

I also like pink just for humiliation sake. I like red as a seductive sort of color in lingerie. Of course other colors are nice, but those are the ones I tend to gravitate to. There were some nice sheer black thongs that I though would be great. I picked out a size I thought would fit and I suggested that he touch the fabric to see what he thought of them.

Then I held them up to him. Hm, that would look very nice on you, I said, as other people strolled by. Some of them giggled and some of them looked embarrassed. We soon had that section of the store to ourselves. I summoned the sales person as I had planned and asked for a consultation on his bra size.

The embarrassed salesperson gave me a measuring tape and I measured his chest size right in the store. He was definitely living up to my expectations and blushing a bright pink.

I picked out a waist trimmer that would make his waist look nice and small and girly. Next we picked out some nice lace topped stockings. In the clothing section we picked out a short little black dress and a slip.

I made a point of holding up each item to him and commenting on how it would look on him. Then we headed for the makeup and jewelry counter. I picked out some nice clip on earrings. I decided on a sexy eye shadow and lipstick.

In the shoe section I picked out a lovely pair of black high heeled pumps, and I swear that I was beginning to feel like prince charming as I handed him a few pairs of shoes to try on. I couldn't wait to get him home to my evil dominatrix lair to make him into my prissy little slut.

The Transformation Sissies have always excited me. And I use that term endearingly. I’ve always been attracted to effeminate men. The first boy I ever had a crush on when I was a girl was a promiscuous little sissy who was the first one in our class to french kiss.

When I was older, I dated an effeminate cuckold who got incredibly turned on when I cheated on him. If I wanted his 8 inches to stand tall all I needed to do was tell him how good it was to be fucked by another guy, or flirt with another man when we went out.

I've always thought it was too bad we hadn't taken his masochism and effeminate nature to the next step. If I had been a little more experimental in my early twenties I might have found that he liked taking it up the ass as well. I've always wondered what might have happened if I had discovered my liking for strap on sex at an earlier age.

The act of dressing someone as a woman is extremely exciting to me and the idea of dressing my friend in the clothes we had purchased was no exception to the rule. I was already fantasizing about how he would look in the dress we had bought as we traveled home from the store.

I let him walk up the steps ahead of me and my wicked nature made me grab his ass in the hallway and give it a good slap.

"How will you enjoy being an object on display?" I asked him.

When we got inside I made him shed his man clothes and I took them into the bedroom and locked them in an old suitcase. I told him that he could have them back if he did his job well tonight. I slowly looked him up and down to let him know that he was my sex toy and an object.

I let him stand there on my carpet in silence, me staring at his nakedness with my big green eyes until he couldn't stand it anymore.

He asked me, "Please may I have some clothes Mistress. "

I looked at him standing there naked in the middle of my living room, trying to hide his semi-hard penis.

I laughed at him and said, "I never said you'd be serving us with clothes on. " I said it just to see his discomfort at the idea.

But what I really desired was to see him all dressed up for me. I pulled out the panties that we had just purchased and watched him step into them. I also cinched his waist tightly. I do love a small waist because it is very nice to hold onto during strapon play. Then I showed him how to put on the bra, first hooking it in front then twisting it around and putting his arms through.

I had to adjust the straps of the bra so that it would be situated over his actual breast area. Just for fun, I rubbed his nipples through the soft bra fabric.

Then I made him sit down and I showed him how to very carefully bunch up the stockings and pull them over his feet and ankles and oh so carefully inch them up his calves, over his knees and up his thighs. I told him how delicate they were and how it was very important to keep his feet and his hands manicured so he wouldn't snag them.

Already I could see that the soft fabric of the panty hose was arousing him and his little clit was standing at attention in his panties. I was amused and pleased at the same time. Next I had him put on the slip and the dress, and slip into his high heels. His response was really exciting me and I felt a familiar pulsing of my clit and a wetness between my legs.

I do love to see someone fully dressed. But we weren't quite finished. I clipped the clip-on earrings on his ears. I also had to apply the makeup. I held his chin firmly as I applied a sexy, seductive coat of lipstick to his pouting lips. Next I slowly evened it out with my finger. Then I made him close his eyes as I applied eye shadow. I stepped back and surveyed my work.

"Mmm. Yes you do look like a little slut now. Lick your lips. I ordered him.”

As he licked his lips, I the wicked thought came to my mind, yes, those lips would look so hot around my strap on dick.

Next I gave him walking lessons. I made him walk up and down in front of me, showing me how sexy he could be. I gave him pointers on how to swivel his hips as he walked in his little black dress. I modeled him in front of a full length mirror so that he could see the full effect of his transformation.

I had to explain to him his duties for the night. I planned on him serving drinks to everyone, and acting as Vanna for the sex toys as I introduced them one by one. I also owed him a good spanking. Who knew what might happen afterwards?

Slut Serves at Toy Party

The evening passed quickly and soon guests were arriving. My seductive sissy toy opened the door and met each person as they came in. My friends were open minded and knew to expect anything from me, so my cross-dressing friend did not surprise or offend them in any way.

In fact some of them were even a little playful and interested in my friend. My young bullish bi curious friend seemed especially interested. I wondered at the time whether it was because he wished he was in my friend's place, or if perhaps he wasn't a little bit sexually attracted to my new "woman" friend.

Soon everyone was there, and my slut was kept busy bringing drinks to people and sometimes enduring slaps on the ass or people copping a feel. I imagine though that he was thoroughly enjoying it despite his blushing face.

We started the toy show and my friend did as asked, holding up each dildo and vibrator and daintily pointing to the finer points of each one as I discussed their merits. As we got to the strap on dildos and began discussing strap on play, my little sissy slut was becoming more and more excited. I could tell by the way his eyes were growing and his pupils were getting larger. Also his trembling told me that his response was indeed a very powerful one.

I announced to my guests that if everyone was willing that we could have a more practical hands on type of demonstration of strap on techniques. Anyone who felt uncomfortable was welcome to excuse themselves.

Noone wanted to leave.

I asked my lovely sissy assistant to come front and center. I would now refer to my friend with female pronouns, because the sexual initiation she was going through would thoroughly accomplish the task of allowing her to open to her Mistress in the most feminine way.

I told everyone that my little slut had been so naughty earlier this evening and that I had promised her a good spanking. I moved various display toys and bent her over my display table. I pulled up her little black dress to display the tops of her sexy stockings and her little black thong leaving nothing to the imagination. Although she was reluctant, she had consented in advance to what we were about to do. But I knew that psychologically she needed to know that she had no choice in giving herself over fully to submitting. The spanking would give her a way to save face, and would provide the motivation that she needed to go all the way.

I spanked first one cheek then the other. They were beginning to look a nice hot pink as I humiliated my little slut and told her what a naughty little sex toy she was. I continued spanking her and watched her maneuver to get out of the way of my spanking hand. I told her to raise her bottom higher for me. And I kept spanking until she resigned herself to the spanking and began to beg me to do what I wanted to her. I asked our audience whether they thought I ought to demonstrate strap on techniques on her.

Someone asked how to prepare for strap on play. I took out a non-latex glove and some lube and squirted a generous glob of gel onto my finger.

I said "Lots of lube is helpful in anal penetration. " I shoved my middle finger in my little slut’s ass. I probed slowly and deeply and felt her little puss tighten up around my finger. I commented on how tight she was and said gentle probing would eventually lead to relaxation. But if not you could always suggest that the submissive try to push your finger out with their sphincter muscles.

That seems to have the effect of loosening them up. As I was talking I was pushing my finger in and out of my slut and watching her seductive ass push up to my finger. I decided she needed more, so I slid a second finger inside her, gently working just the tips of my fingers in. I slowly worked my fingers until I was up to the second knuckle. Soon I was burying two fingers deeply inside her. I said, "As you can see, this little BITCH is aching for more. You can tell by the way she pushes back against my fingers that she wants to be taken.

" I slowly slid two fingers all the way inside and pushed deep inside my little sissy. After a couple of minutes, I said, "Okay, now she feels relaxed enough to fuck. Does anyone else want to slide their fingers inside her to see what a relaxed ass would feel like?"

There were a couple of women who volunteered, giggling as they donned gloves and inserted fingers inside my now blushing and totally willing sissy. In fact, she was getting thoroughly excited by all the attention, and her voice was getting high and she was moaning like a girly girl.

Next, I demonstrated fastening the strap on harness and my assistant sissy snapped the harness closed for me, although probably a little weak in the knees.

Then I had her select a dildo for the harness. She selected a nice beaded silicon anal plug which had graduated beads and was about 6 inches long. The end bead was about 1 inch and the one at the base was closer to 4 inches around. I slipped the beaded anal plug into the strap on harness and explained that plugs or dildos could be used in the harness as long as there was a base of some kind on them. Again, I demonstrated the use of lots of lube on the toy.

I pushed the now trembling sissy down so that he was leaning with his hands on a chair, with her side to the audience so that everyone could see what I was doing and see his expression as well. I held the beaded toy in my hand and rubbed it against his ass.

I commented that it was fun to tease with the strap on until the bottom begged to have it inserted by just rubbing the round lubricated end of it against their ass. I also suggested that particularly an oral submissive might also do well to have their oral fixation fulfilled as well as their anal one. Gags work well, but be sure that your submissive has a safe signal since their mouth will be filled.

Or perhaps if you have willing volunteers, a nice juicy cock to suck on, might work very well. I was looking at the shy 25 year old hunk and thinking that I'd love to see him get his dick sucked for the first time. I asked him directly, "Would you like to volunteer?"

He replied, a little embarrassedly, "Yes, I would. " As he stepped forward and pulled down his pants, I watched his young 9 inch cock spring out of his shorts.

"Mmm." I thought to myself that I would really enjoy the sight of that big juicy cock getting sucked.

I told my sissy friend, "Suck it for me you little bitch. " I knew my friend was eager to please me. And I watched her amateurish licking tongue as she eagerly devoured the young hunk's throbbing shaft. She began to get the hang of it and I noticed that our guests were getting noticeably turned on and some were openly masturbating as they watched. Our session seemed to be turning into a circle jerk.

I rubbed the beaded toy more firmly against the sissy’s tight little hole and pressed until I watched the first round bead slick with lube disappeared in the slut's tight cunt. I pressed a little harder and the second one slipped a little more tightly inside, stretching her tight little pussy wide. I pulled out and pushed slowly back in watching the two beads disappear in and out.

S/he was totally turned on right now and moaning on the hot cock in her mouth and pushing back against the toy in her ass. I pushed a little deeper and watched the third bead slip inside.

It was still only a little more than half way in. A good 2 ½ inches were still not inside. But the third bead was really good and tight and I hesitated at stretching him/her any wider. I funked the little slut good, watching those three beads disappear in and out of her tight little ass. I could tell that the hunk was going to unload soon.

I reached around and started milking my little sissies cock really fast. I wanted her to cum when that stud filled her mouth up with warm creamy cum. I rubbed her softly and quickly. I stroked and milked her swollen clit until I could feel the cum rising up inside. It was now or never.

I firmly pushed the last bead inside my horny little slut as I milked her cock of its' cum. Just as she was moaning and growling against the stud's cock, he shot as well, filling her mouth good. I watched as it dribbled out the corners of her mouth.

"Mmm. What a good little sex toy bitch. What satisfaction and power you give to your Mistress when you submit." I knew that this was a milestone in her life. To give me the gift of her cherry ass in front of a room full of people was indeed a true gift to her Mistress.

I never allow my submissive to see me cum, but I enjoyed myself afterwards. It took very little time for my vibrator to do its' work.