The New Sissy Club Pt. 01

Many years ago, when Craigslist was popular for dating and sexual encounters, I used to like read ads. I happened upon an ad in the "Men Seeking Men" section. It was titled "Sissy Club Forming." The title intrigued me and when I clicked it, I read:

"Sissy Club forming for pantied crossdressers and sissy men. Private and discreet. For more information reply back to Phil."

I must have clicked on and off that ad 10 times. I really didn't plan to respond but then I thought what could it hurt just to find out more?

So, I responded: "Hello, Phil. My name is Carl. I've been a closet crossdresser for many years and I'm interested in learning about your club."

In less than hour I got this response:

"Hello Carl. We are all like you, most of us closeted crossdressers. This is your opportunity to live out your fantasies and dreams with other sissy men and 'come out' and expose yourself in a very private and safe setting. I hope you will strongly consider joining us. So far there are two of us. You would be the third, hoping to continually ad others. If you're serious, respond back with, 'Yes, Phil, I'm a sissy CD and wish to expose myself with other sissy men like me.' If you do so, I will send you the rules and details of where and when we will meet."

I was nervous about it, but this might be my only chance for this.

About 30 minutes later I sent this to Phil: "Yes, Phil, I'm a sissy CD and wish to expose myself with other sissy men like me."

He wrote back:

"Good girl, Carl. From now on you will be Carly with our club. I'm Phyliss. Our other member is Rob (Robin in our club.) Here are the (so far) established rules, but they are subject to change."

1. You must provide a negative STD test.

2. You must dress fully at a club meeting including a wig. A bra and panty must be worn under all outfits as well as hosiery. Make-up is optional except for lipstick, which is mandatory.

3. You must be willing to expose yourself to the group (penis, balls, ass, tits, etc.)

4. You may be fully naked at times.

5. You must be willing to touch and feel all other group members, as asked, or directed, as well as perform oral and manual stimulation to the other sissies.

6. Sissies must ask if they wish to kiss another sissy. While you may not think it now, believe me, it will happen for you!

7. Anal sex is only allowed with permission from both participants. But you must keep your anus clean for all meetings as anal fingering is permitted and encouraged.

8. You must be open to prostate massage and milkings as well as performing both for others. (Look it up if you don't know what it means.)

9. You must ask and receive permission if you wish to tongue-rim another sissies anus.

10. Your bottom must also be kept clean and available for another sissy to rub himself off between your cheeks from behind.

11. You must be willing to accept some things that you find embarrassing, uncomfortable (at first) and possibly humiliating. But remember you will be among sissy friends who will feel the same as you. Over time and more exposure to certain things, they will become normal and even enjoyable for you when asked to perform them.

12. Toys (anal plugs, pussy sleeves, dildos, etc.) will only be permitted by group vote.

13. No cock cages or chastity devices are allowed.

14. You must be willing to masturbate in front of the group.

15. You must be willing to taste cum and swallow at times, including your own.

16. Nothing that happens at a meeting ever leaves the room. It is strictly private between club members. What we do here, stays here. You must sign an agreement. No pictures, recording devices or videotaping is allowed.

17. You must always be honest and open with all your thoughts and feelings with the group. Even if it's embarrassing to admit them. Your secrets remain here.

18. The only age requirement is that you be over 21, but no limit to upper ages and all body types are welcome.

19. No negative comments about other members will be tolerated. But helpful critique is encouraged as regards to clothing choices, make-up suggestions, accessorizing, etc.

20. Comments regarding penis size is a normal activity, whether complimentary or humiliating. Sissies always love to talk about cock, no matter what size. (Note: The smallest male in the group will always be teased.)

21. You will be asked to leave and never return if you break any of the rules.

22. You may also leave the group at any time on your own, but you will never be allowed to return.

23. To protect the privacy and integrity of the group, all new members going forward will need to "audition" and be approved by the group majority.

He included the address of a local hotel and told me the next meeting was going to be the following Saturday at 11 am. The email said to bring my suitcase with at least two outfits packed and one bedtime outfit (lingerie, nightgown, etc.) I was to reply if I agreed to all the rules and planned to join the meeting.

I never imagined myself doing anything like this but just reading the rules was making me hard. I masturbated thinking this would calm me down and I'd clear my mind and get over this. But the masturbation didn't help. 15 minutes later I was back at my computer. I knew I had to try it. I wrote back: "I agree."

The rest of the week leading up to Saturday I was looking at my outfits trying to decide what to take. Since I've been living alone (divorced) for the past few years I had started shaving my legs on a regular basis about a year ago. I learned from a lady friend that it feels so much smoother that way with stockings. I have very little chest hair, but I removed that as well and also shaved my armpits. I'd never done that before. I always left my bush intact but decided that I should shave it off for this, so Friday night I shaved and I sculpted a little landing strip above my penis. I used a depilatory on my balls to smooth them out completely. I must admit it looked and felt great to be so nearly hairless and imploring such a very feminine-looking body. I showered Saturday morning and checked again for any hairs I may have missed. I put on jeans and tee-shirt with men's boxers underneath. Phyliss didn't say anything about wearing panties to the meeting and I didn't want to presume anything at this point. Phyliss texted me the room number and I headed out.

I had no idea what Phyliss or Robin looked like or their ages. Phyliss sent me some general information but that was pretty much it. I was pretty sure I would be the senior in the group being in my sixties and hoped that wouldn't offend them.

I knocked and the door opened.

"Phil?," I asked. He just looked at me. I tried again. "Um....is Phyliss here please?"

He smiled and said, "Yes. Please come in. You must be Carly. Robin called. She's on her way.

"Do you want to take the bathroom for some privacy to get dressed? I'll use it after you. Then we can wait for Robin to dress and I'll pour us all some wine. When we are all dressed, we usually greet each other with a little kiss on the cheek. You don't need to ask permission for that. It's just a nice way to greet each other and get things started."

I hesitated and looked nervously at Phyliss. Phyliss was tall; over 6 foot; probably in her mid-forties. A nice-looking man with a nice smile and a soft, comforting face. I already began to wonder what those long legs would look like encased in nylons.

Phyliss said, "Don't be embarrassed now. We all know why we're here. You signed up and agreed to this. It's what you have long desired. We all have. You are a sissy, aren't you Carly?"

"Yes, I am Phyliss."

"Say it, Carly. It will help you through this and give you more confidence."

"I'm a sissy, Phyliss."

"Good girl, Carly. Now tell me why you're here."

"I'm a sissy," I replied. "I want to show myself to you and Robin....dressed in my pretty women's clothes. I want to show you my stiff little penis in soft pretty panties. I want to wear my nylons and high heels in front of you."

Phyliss said, "Carly, that was good. Don't be afraid to admit your desires. I know you've wanted this. It's hard to admit that you're a sissy. But you're here and you're finally ready now. To come out of your closet. To expose yourself as a sissy. I know you want to kneel in front of me, like a good girl; to take my penis out of my panties and suck on me; like a woman, like a girl does. That time will come for you, and it will make you very happy and at peace with yourself. But now, I want you to show us. Go in the bathroom and get dressed. Show me the sissy you've always wanted to be."

It was still embarrassing for me, but he did make me feel better with his words. It is what I've wanted for so long. I picked up my suitcase, went into the bathroom and closed the door. I don't look feminine at all, but I know feminine dress. I used to pick out clothes for my former wife, although that was over 25 years ago. But she used to say I had excellent taste in women's clothes. Like many crossdressers I used to play with her clothes when she wasn't home, but she was never really aware of my perversion. I can trace back my crossdressing to my late teens. What did surprise me was early on in our marriage my then wife bought me a pretty purple and cream-colored long women's nightgown. She said she wanted us to feel soft together in bed. So, from then on, we both wore nightgowns to bed. Unbeknownst to her, that increased my desire to wear more women's clothes.

I unpacked a red pleated skirt that would flow and open easily from underneath. It came about 3" above my knees. I had a black and red loosely fitting blouse top. I put my bra on first, a red 40A. Some say "man-boobs." My ex used to say I had "baby-tits." So, the 40A works for me without using padding in my bra. I brought nude stockings; the old-fashioned kind that require a garter belt to stay up. I put the matching red garter belt (that matched my bra) on first and rolled the stockings up to attach them to the garter straps. A matching pair of full cut red nylon panties completed my undergarments.

As an older man I sometimes have ED issues, but I was already getting semi-hard just getting dressed. I added my blouse and skirt and slipped into my red, shimmery 3" heel pumps. I have pierced ears, so I added gold long bangles and a gold necklace with little butterflies on it. The wig I brought was a curly, short haired style so it would leave my earrings exposed. Since lipstick was a "must" in the rules, I used a closely matching shade of red to accentuate my rather large lips without trying to look too "slutty." I wanted to look ladylike, especially for my first time. I had a little red clutch purse, so I put my lipstick in it along with some tissues. I wanted to be prepared for anything that might happen. I rechecked everything in the mirror and went out to meet with Phyliss, clutch purse in hand.

Phyliss was sitting on the bed and looked up at me. I bowed my head feeling a little ashamed.

Phyliss said, "Very nice, Carly! Nice choice on your outfit today! I can't wait to see what you have on underneath! Turn around for me!"

I turned and sort of twirled my skirt around in front of her. I couldn't help but notice that Phyliss had a bulge in the front of her pants! I'm fairly used to wearing heels ( I do that at home), so I walked over to the table and chairs near the window, tucked my skirt under and sat down, crossing my legs demurely at my ankles. Phyliss got up, took his suitcase and headed for the bathroom.

She said, "Just make yourself comfortable. I'll be back shortly."

There was a knock at the door. Phyliss called to me, "Will you get that, Hon? That will be Robin."

I thought to myself, omg, he's going to see me like this for the first time! I walked to the door and cracked it just enough to look out.

He said, "Hi. You must be Carly. I'm Rob. Robin."

I opened the door and he said, "Wow, you look great!"

I blushed and said thank you.

He said, "You know all the rules, right?"

I said, "Yes, but I printed them out and put them over on the desk there just in case I forget any of them."

Rob said, "Rule 5. May I kiss you, Sissy?"

My heart pounded a little faster. I was taken aback. I loved that he called me Sissy and asking my permission! It felt girly and sweet to me...to be asked.

I just blurted out, "Yes....Rob (soon to be Robin)....you can kiss me."

He was a little taller than me, even with my pumps, so he leaned down, put his arms around my waist and pulled me into him; to his lips and I felt my first "sissy-kiss." He pursued another few seconds and slipped his tongue into my mouth. I accepted it and tickled back with my tongue. I felt oddly strange but very girly, dressed and kissing like this. I just kissed a man! Just then the bathroom door opened, and Phyliss came out and caught us kissing.

Phyliss turned to us and said, "Well, I see you two have met! Carly submitting to a kiss already? I presume Robin asked you?"

"Yes," I said, "He did."

"And how did that make you feel, Carly? Remember the rules, Carly. You must be open and honest about your feelings, even if they embarrass you."

I told Phyliss, "I felt tingly, excited...in my head...in my stomach...and down below...you know...in my panties."

"Good Carly. Sissy-kissing with men is very exciting. You're going to find it very enticing, very sexual, very arousing. The stirring in your panties is a very good sign, Hon. It means you're accepting your feminine side and it excites you to sissy-kiss. It's really just a very first step, but the more you kiss the more you'll want because you get that tingly feeling in your panties, Hon. Maybe later today, Robin can sit in your lap and you can sissy-kiss while you hold and fondle his penis and balls under his dress and feel him in his panties. Do you think you would like that, Carly?"

I felt ashamed and didn't answer.

"Carly, what did we just talk about? About our thoughts and feelings. You can leave right now or appreciate that I'm trying to help you be honest and open. Don't make me ask you questions repeatedly, Carly. I would like an answer. Would you like that, Carly? Look at me and tell me, Carly."

I trembled and finally said, "Oh, yes, Phyliss. I would like to sissy-kiss with Robin while I fondle his penis and balls. I would feel so tingly and excited!"

"Good. That's a normal thought, Carly. There's no reason to feel shame." Phyliss towered over me. Her six-foot plus frame, now standing in 3" black heels and looking prettier than I could have imagined. She had a beautiful, long blonde wig, eye shadow and dark red lips. She wore a slinky black dress, mid-thigh with very sexy black, back-seamed stockings. I couldn't tell if she was wearing a padded bra or not. I was in awe.

"Phyliss," I asked, "May I kiss YOU?"

"Yes, dear, you may," as she backed me into the wall behind me and bent down to my level. We both smeared our lipstick with that kiss and went to the mirror to freshen up.

"Did that make you leak and tingle...in your panties again, Carly? Tell me how you feel."

She didn't have to ask me twice this time. "Yes, yes, so very tingly! I think I wet my panty already too!"

Robin had been watching us the whole time. Phyliss said to him, "Please get dressed, Robin. We're waiting for you."

I was guessing Robin was probably in his mid-thirties. It's probably why I was so excited that he wanted to kiss me being nearly half my age and he still found me attractive as a woman; or at least dressed as one. He was taller than me and had a nice slender body. Easily the most physically fit of the 3 of us. He came out of the bathroom wearing a white miniskirt with white stockings and white strappy sandals! I must admit, he looked hot! Or was it she? His skirt was so short that when she sat down to join us, I could see the bottom of her ball sack in her white panties on under her skirt! It appeared that she must have padded her bra under the pink top she was wearing as she had some rather nice tits under that blouse.

Phyliss poured us all a glass of red wine and we chatted for a bit, learning more about each other, all together now and fully dressed with each other for the first time. I explained that I was divorced and always found myself attracted to women's clothes. Phyliss was married but his wife didn't know about his obsession. Robin had a very open-minded girlfriend who encouraged his dressing with her. She had found the Craigslist ad for him and suggested he join the group! She helped him with his make-up and clothes. Robin asked if she, Kate, his girlfriend, could join the group sometime...strictly as a spectator. I found the thought of that exciting! Phyliss said he thought it would be ok and would decide when we would invite her. Maybe after we have another member, he told us. Phyliss and Robin had met twice before I became the third member. It was Phyliss who posted the original ad and obviously was the superior in the group. I don't know what Phyliss and Robin did at their first two meetings.

To get things started, Phyliss put a DVD on for us to all watch. I couldn't help but stare at Phyliss's long legs in those black sexy nylons. She had beautiful, curvy calves and slender ankles. Robin's ball sack was still exposed in her panties sitting across from me. I had that tingly feeling in my panties again. The DVD was 3 older gentlemen with two crossdressers, both dressed as maids, in typical black and white maid outfits, serving coffee and tea to the men. When they bent over to serve the coffee, the camera angle showed them both wearing no panties and we could see their penises and balls under their dresses. The 3 men seemed to show no real interest in the sissies except as servants to them.

As the men sipped their coffee, the two maids started unbuckling the men's pants and taking off their shirts. This was hot to watch! The 3 men stood up and the sissy maids finished undressing them. The two sissy maids kissed! And then the 3 completely nude men sat down, all had hard-ons, and the maids went to their knees in front of them. The sissy maids began taking turns on the men's cocks, one being stroked while the other two filled the sissies' mouths with their cocks. They bobbed up and down on the men's poles. The camera again panned from underneath, and we could see how "happy" the sissies appeared to be with erections under their dresses. The two sissies were caught several times on camera reaching under each other's dress to stroke each other's penis for a few seconds each time. But they were totally focused on the men, really enjoying their cocks and pleasuring them.

The 3 of us at this point all began sporting our own erections, our dresses and skirts tenting out our panties. Phyliss's bulge pushed her slinky dress out the furthest. I assumed at this point that she would have the largest cock. After all, she was also the tallest. It appeared I would be the smallest man there, my skirt barely prompting a small lump in my red skirt.

Phyliss asked me, "Carly, does this excite you? Watching the sissy maids with these men? Is that something you would like to do? Are you tingly and hard in your panties?"

I didn't hesitate to answer this time. "Yes, Phyliss, very excited and tingly. I would like to dress like those girls and pleasure those men!"

"That's right, Carly. I knew you would. Now stand up for us, Carly," Phyliss said to me. "Lift your skirt and pull down your panties. Let's see how excited and tingly you really are. Hold your skirt up and show us your undergarments and penis."

I stood up but now I got nervous again. Phyliss and Robin were still fully clothed. Phyliss now more forcefully said, "Carly, Rule 14! 'You must be willing to masturbate in front of the group.' It's your choice, Carly. You can leave now and never return or skirt up, panties down, Carly! "