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Sissy panty boy phone sex for a sissy slut wanting tiny cock humiliation

By Sissyplaytime May 23, 2025 Humiliation phone sex, Sissy panty boy phone sex

Recently, I had a really hot panty boy phone sex call. The caller is a little sissy slut and a sissy faggot who wanted a good dose of cuckold humiliation phone sex. At the beginning of our call, I dressed this naughty sissy panty boy up, in a sheer hot pink teddy with matching sheer hot pink panties, black, tall high heels, and bright red lipstick. I had to make her lips look good, because she was soon going to become my cock sucking faggot. Shall I make her into a fluffer, I do know that not all sissies are into this. For now however, I tied her down to a table, had her splayed out on her sissy back, spread eagle.

This naughty sissy was so excited as she received my wicked small cock humiliation that I like to do during a sissy humiliation phone sex call. I also managed to call her some vulgar, humiliating names, as I invited in three men with really big dicks to compare her little dick to. These studs took turns fucking my pussy, as this poor sissy stood in the corner, little clit out, stroking as everyone laughed at her. I had a good gang bang, while this sissy watch the three well hung men fuck me with their rock hard cocks.I did manage to put the little dick sissy to good use. She gave me a good ass licking and I fed her my cream pie. I think I will turn her into a cum eater for me. That’s a good idea I think, she seems to love cum already!Call Ms. Cassie for your sissy phone sex and humiliation at: 1-877-368-7505

Sissy training phone sex |Debbie | Ms. Jennifer 1-877-368-7505

By Sissyplaytime May 22, 2025 Cross dressing phone sex, sissy training phone sex

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Sissy training phone sex with my new cross dressing gf Debbie. I have a wealth of information about a new trainee she is very willing to embrace being feminine. I am going to be posting in a few updates – starting with the very beginning. This is so you wannabee sissies will be able to learn and possibly dress up like Debbie does.

She contacted me originally wanting to know what I thought about her dressing up for the first time. She is lucky because she already has a boyfriend in mind. She told me that she called him and informed him to get her some lubricant and I also mentioned some lipstick (I had suggested these). He did. Afterwards, she told him, if he wanted me to do so again, I would need more lingerie and clothes. He agreed and said he would get some more. I will call to inform you how it all went.

I was so happy when I found out that she told her bf to get the items I had suggested to her on the phone. After her bf came over, she said “Oh, what I didn’t like, I had cum dripping out of my sissy butt while working last night. I had to go to the restroom and put paper towels in my underwear. I wasn’t prepared for that. Does the seeping normally happen? If I continue, should I get some panty liners like women do?”

That is pretty funny. I had to laugh when I heard that, but told her it was perfectly normal. I also suggested that she start getting some female things, like lingerie and makeup. This is what I heard back, He called and informed me, he has some cosmetics (eye liner, mascara, a small box eye shadow, lip liner) bra, panties and a peignoir set (I had to look it up). I asked him where he got them, he said he asked his sister to pick up. She is aware that he likes his guys in lingerie but doesn’t know who I am and that he pays her back for her expenses. I told him to get some panty liners from her. He agreed and said he will be over around 6. We both have to be to work at 11pm.

I was very excited when I heard this. I think Debbie is moving right along. That night he came over to visit Debbie, this is what she had to say “He helped me put the bra on and now I have to try and put the makeup on. I feel so excited. I can’t help it.”

I will keep all you sissy’s posted on Debbie’s progress.

Ms. Jennifer 1-877-368-7505

Humiliation, pain, chastity during sissy phone sex call with Ms. Vanessa

By Sissyplaytime May 20, 2025 Humiliation phone sex, Sissy Phone Sex for Panty boys, small penis humiliation phone sex

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Vanessa

Ms Vanessa just did a super fun sissy phone sex call with tons of humiliation, chastity and pain, with MY sissy Martie, she is a sissy whore and likes pain and sissy chastity. She had a few clothespins, and a whip, I own and control her, and wasted no time in getting her on board so that I can use her sissy mouth and ass for my amusement. She started out by licking my perfect ass, and I put clothepins on her balls, and tits, and thighs. I spanked her sissy ass, and we talked about getting a dildo and butt plug, and more panties.

I like spanking her clitty during our sissy phone sex call, and I plan on using her more in the future as she is a dirty little slut. Did I mention her clit is small, small penis humiliation phone sex ranks high in my favorites. Martie likes to be humiliated and abused and needs that sissy spanking on clit and ass to remind her of what a sissy whore she is.

Ms. Vanessa for sissy phone sex at: 1-877-368-7505
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Panty boy phone sex

By Sissyplaytime April 15, 2025 Cross dressing phone sex, foot fetish phone sex, panty boys

Panty boy phone sex, is great. I enjoy talking to panty boys. I have always been attracted to guys I who I could dress up like I wanted to. I can promise you one thing, and that is that I will want to dress you up from your panties to your heels. Your dream will come true as I turn you into my little girl! Plenty of sexy girlie clothes, lingerie, panties, makeup and perfume to top it all off. Perhaps you are looking for a cross dressing phone sex session. I need to know exactly what type of feminization you desire. Would you only want to be dressed up, and then have lesbian sex? Or wouldo you like to or want to suck dick, do you like only real girl pussy? Would you like your pussy to be used. Even though I am in charge, it does not mean, the session goes my way. It goes my way in the fact that I do it as I see fit, but will custom tailor your session to suit your fetish needs.

I could have you out all night making you the biggest cum whore in town. You might be sucking, licking, and fucking and your pussy will be so sore by the time we are all done with you! How many loads of Cum can you swallow in one night? Oh let’s do find out! My feet are wonderful. I bet you’d just love to have them pressed against your face or cock. Licking and smelling them before I use you.

Ms. Audrey 1-877-368-7505

Sissy panty boy phone sex – let’s grind together and play

By Sissyplaytime April 6, 2025 sissy feminization, Sissy panty boy phone sex

Mia

Wanna play dress up with me and have some panty boy phone sex? I feel like dressing with you in pretty pink panties and garters with sexy white silky thigh highs. Let’s slide those sexy, soft, silky blush pink panties up over your balls and hard cock. I love the way the panties show off the out line of your beautiful cock. I can’t help but run my hand over the front of your panties.

Doesn’t it feel good to slowly slide the thigh high up your leg? You know it does. I love watching you dress up for me. You are such a good little panty boy and you really do deserve the best panty boy phone sex ever. Why don’t you lie back on the bed and let me climb on top of you. I love the way it feels when we grind together in our panties and thigh highs. Your hard cock in your panties rubbing against my wet little pussy in my panties. Our legs entwined in our thigh highs. It feels so good, faster and faster. Lets cum together in our pretty pink panties. I can’t wait anymore and I can feel your cum squirting through your panties as I cream through mine.

Lets have some fun intelligent panty boy phone sex! Call:Mia 1-877-368-7505

Sissy phone sex with Ms. Audrey

By Sissyplaytime April 6, 2025 Feminization phone sex, pink panties, sissy husband feminization

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Sissy Trainer Audrey

John is my latest naughty sissy slut for sissy phone sex. He is an sissy panty boy addict of my huge strap on phone sex chat, he called me and continually begged me to let him get on his knees, dressed up for me all pretty, and suck my big rubber dick. He knew just how to please me, so that I would cave in to his strap on desires. Even this early into getting to know John, he is already becoming extremely obedient to his Mistress. He will be getting on webcam for our next sissy phone sex session, and he promised me that he would be dressing up in very sexy lingerie for me, while I send him pictures of my big strap on.

John loves femme domme phonesex with a strap on and sissy twist. He told me when he is with his wife, he loves to be on top, so he can try to get his little clitty inside of her as deep as possible, but of course, neither of them remain completely satisfied, he can’t feel the walls of her pussy, and she can’t really feel his little dick. But with me, he is my bottom, he knows that he is my submissive sissy slut. I commanded him to beg for my cock, to show me how much he wanted my big rubber dick with his mouth and his cocksucking skills, and since he was such a good sissy slut, he did end up getting my big rubber dick jammed right up his man pussy.

For sissy phone sex call Audrey at 1-877-368-7505

Sissy cross dressing training phone sex | Debbie | Ms. Jennifer 1-877-368-7505

By Sissyplaytime March 23, 2025 Cross dressing phone sex, lingerie, sissy phone sex

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Whether it is sissy cross dressing phone sex training or feminization, I am the phone sex Mistress for you! I have been having a great time helping Debbie find the feminine side. She is fabulous, and I love the updates she sends me, she is also getting help learning about being a girl from her boyfriend’s, sister. She was hesitant at first at having his sister help him decide about clothing and makeup, so with my coaxing and her eventually going over to Debbie’s house, Debbie is now quite a creation. She has sent me photos, and WOW, she looks incredible.

She called me today and told me her vagina panties arrived and will be wearing them tonight. These panties have a vaginal in the crotch. Debbie said there is a hole in the vagina making her able to even sit and pee in her vagina panties. I guessed that they were flesh colored, and I had suggested breast forms, which she did purchase. So with her breast forms and pussy vagina panties she is now a real girl. She told me that it gives the illusion if you wear jeans to look like a pussy. Does this mean you have a camel toe? Debbie is going to wear her new panties tonight. She has a date with her boyfriend and he is going to bring over his van. She will wear a cocktail dress, Debbie said it is for easy access, meaning he can have access to her ass. We talked about when she gives him a blow job, if she wants to get her ass fucked, then she needs to be sure, he does not cum in her mouth. Then when he finishes, she told me he will suck her cock. She is so lucky to have a great boyfriend. She will try her vaginal pussy tonight for the first time.

We also had a pretty interesting discussion about lingerie and pantyhose. She told me she gets hot sleeping in her bra and stockings, I suggested a baby doll nightie. Also she gets a lot of runs in her pantyhose, and her bf’s sister told her to save the panty hose, cut off the side with run, and then wear two pairs. I never heard about this tip. It’s a good one!

I will keep you posted on Debbie’s date and her new vaginal pussy!
Ms. Jennifer for your sissy feminization phone sex training 1-877-368-7505

Look in your wife’s panty drawer and call me for panty boy phone sex!

By Sissyplaytime July 22, 2024 panty boy phone sex, sissy husband feminization

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Amy

I am in the mood to play during a sissy phone sex fun playtime call, with someone wearing sissy panties for me, who maybe thinks he isn’t a real man, most likely with a small penis, and a fascination for womens’ clothing. When your wife is not around, that is the best time for some sissy husband feminization phone sex. Let’s dig through your wife’s drawers together, maybe even through her dirty laundry. Report back on your findings, what colors, fabrics, and cuts of panties does she have? While bras are great, does she happen to own any corsets? Any sexy lingerie? Revealing, sexy clothes? Let’s get you all dolled up and looking your sexiest.

Call Amy for sissy phone sex at 1-877-368-7505

Ms. Vickie wore a school uniform

By Sissyplaytime June 17, 2024 Cross dressing phone sex, sissy

sissy phone sex Wow, I had a lot of fun last night with Ms. Vickie. She got dressed up in a school uniform. I took her to the lingerie store and we had her fitted for a new Bali flower underwire 32B bra, in sissy pink. She had on white cotton panties, and then we got her a little very short plaid skirt, blouse, with a tie, stockings over the knee, mary janes, and some lip gloss.

I could not resist, I sat next to her, she looked so lovely and adorable, I kissed her on the lips, and Auntie is a naughty girl, as My pussy was so wet. I slid my hand under Vickie’s skirt and played with her big clitty. Before you know it, I was sitting on and and riding her. We had wonderful lesbian sex.

I am looking forward to dressing Vickie up for school.

xoxo’s Ms. Kate for sissy cross dressing phone sex 1-888-833-1586

Sissy phone sex dress up at the lingerie store with Ms. Vanessa

By Sissyplaytime June 15, 2024 Cross dressing phone sex, Feminization phone sex, lingerie, sissy phone sex

I do enjoy playing dress up with a sissy gurl during sissy phone sex. I have many sissy’s that call me, and one of my favorite sissy panty boy’s has a favorite sissy fantasy that he likes to role play with me. It is about me milking him, and when I give him a thorough sissy milking. In this particular fantasy I am the owner of a custom lingerie shop, the reason I am in this business is because I like to incorporate my preference for sissy cock into what I do as an occupation as well. Basically I love lingerie, and also love sissy gurls who love it as well. I get to live my fantasy in real life every day. I often close the shop for personal fittings with special clients. Imagine this could be you! Think about you walking into my shop, and being greeted with open arms. You are given the extra special attention that you so desperately crave.

If you are shy, I might have to coax you into one of the private back rooms with a full size bathtub. There I would I proceed to shave you from head to toe. I want you all lovely and smooth, so W/we will shave you all over. You will wear slinky, silky, underthings that I will pick out for you, this will be just the beginning of a wonderful afternoon romp.

For your sissy phone sex call Ms. Vanessa at: 1-877-368-7505

Are you 18 years of age?

Feminization – training – cross dressing