The New Sissy Club Pt. 04

While we were all dressing for our next "club meeting" Robin and I happened to be alone together in the bathroom, adding our jewelry and final make-up touches. Robin was easily the most passable among us, dressed the sexiest, had the largest cock, and for some strange reason had a fascination with an older sissy-guy like me. She especially loved to kiss me, and it always thrilled me when she did.

There's just something so secretively sexual and erotically charged when two crossdressers kiss and knowing we both have hard-on's while doing it. I doubt I would have ever kissed a man as a straight guy, but as a sissy all my dreams were coming true. He made me feel so womanly, even though it was more like two women kissing when we were dressed this way. The difference was two lovely erections in our panties as we kissed. We watched each other in the mirror applying our lipsticks. Robin turned to me. Knowing she didn't need to ask me (per club rules) in private since I gave her my prior permission, Robin turned her head towards me, leaned her head left and I leaned with her to allow our lips to meet. I closed my eyes. Our lipsticks meshed over our slippery lips. She whispered, "Oh, Carly, you kiss so passionately."

I loved hearing that. I loved feeling that. She circled my lips with her tongue. We sucked each other's lips, opened our mouths and our tongues entwined. Robin made me hot and excited, and I wanted to touch her cock. I reached under Robin's sundress and felt her heavy, smooth balls and felt her hard cock through her panties as her tongue darted in and out of my eager mouth. I loved the feeling of submitting to Robin as the sissy I felt like inside. I wanted her to keep kissing me while Phyliss and Alice had no idea what was going on in the bathroom while they dressed in the bedroom suite. Pre-cum was already seeping into my own panties and I felt the same on Robin's panties as I held on to her cock and stroked her though her panties. Robin's breathing was getting heavier. She whispered, "We better stop and join the others."

I said, "Robin, please, just let me make you cum," as I continued to rub her through her panties. "Please, Robin, I want to." While I had always fantasized for years about moments like this, I never thought I would ever experience them, let alone me saying these words to another man, while holding his cock! I wished this group would have existed many years ago, to bring me out of my seclusion. I could have never admitted this when I was married and trying to play the macho husband role. At this moment, the tingling in my panties told me this was where I was meant to be. I wanted to stroke Robin's cock and make her cum. Robin moaned and put her forehead down on my shoulder. Her cock was so much larger than my dolly and it thrilled me to hold her in my hand. I told her, "Robin, I'll clean you up and you can put on fresh panties and no one will know. Please just let me make you cum. Just say yes."

Under her labored breathing she quietly whispered, "Ok. Yes, I want you to make me cum."

I replied, "Pull your panties down a little...and kiss me."

Robin wiggled her silky panties down around her thighs and held her dress up. She looked lovely for me, pointing her joystick towards me. I grabbed my tube of lube from my make-up bag and worked the lube over her swollen shaft. I wrapped my hand around her thick shaft and began jacking her off. She moaned again and kissed me hard. She pushed her pelvis forward, in a fucking motion, and said, "You're going to make me cum, Carly!" Not wanting to mess up our dresses I quickly grabbed a towel with my free hand and brought it over her cock and my hand while I finished her off. Robin shot several huge globs of his semen into the towel. I cleaned her up. She kissed me again and we went to join the others. My panties were still damp.

We were only alone together in the bathroom for maybe 10 minutes, but we didn't want to keep Phyliss and Alice waiting. There were no specific rules preventing us from doing what we did in there, but we didn't want to hide our actions from the others. After all, that's why we were all here. To allow our sissy-side to be seen by other sissies. It didn't feel "gay" to any of us really. Not like two naked men in bed together having some sort of sex. This was a feeling of sissy men, who loved to cross-dress and feel accepted, even though we all loved feeling each other cocks. I guess Robin kissing me could be seen as gay, but to me, I felt womanly as she held and kissed me. I felt like I was out of my male body and transformed into an effeminate sissy. Sometimes I admit I had wondered what it would be like to have a pussy, but the fact remained: I liked that I had a hard little cock---my little dolly, as the other's called mine, between my legs. And I liked reaching under a "woman's" dress and finding her penis! It's the real reason we are all here. There's nothing more exciting, at least to the four of us, as wearing panties, bras, stockings and dresses together and knowing what we all have between our legs.

When we joined Phyliss and Alice in the big room, the girls looked lovely. Alice was wearing purple again, her favorite color. Phyliss wore a long green dress with slits up both sides showing off her long sexy legs with sheer black nylons underneath. As always, she took charge and wanted to discuss something with us. She informed us that a woman named Pam contacted her through the Sissy ad on Craigslist. Phyliss said her email was very polite and didn't want to intrude but had something she wanted to offer us. She said she was a young photographer, in her 20's, wanting to build her erotica portfolio and reputation, and asked if she could take pictures of us. No faces if we wanted them that way. But she wanted to create interesting poses and scenes featuring crossdressers, and since the Craigslist ad said, "Sissy Club," she said she would like to take pictures of sissy men and hoped that it was ok to refer to us that way. She promised they would be artistic, tasteful, and professional, and suggested besides for her portfolio, we could use the photos for public viewing on fetish websites, or possibly to attract new club members, or just for our own personal club use.

She said there are men and women who love looking at pictures of sissy men and seeing a group of us individually and together would be even more enticing to viewers. She included several shots of nude women and solo crossdressers she had photographed and wanted to do individual and group pictures of us together. She suggested we could do some shots fully clothed and then progress to more revealing, in lingerie, panties, bras and stockings. She said she even wanted some shots with erections if we were willing to do that. Phyliss said Pam seemed very sincere and corresponded respectfully with her. She asked for our thoughts about doing this.

We all seemed to agree that this would be an exciting step for us but wondered about exposing ourselves to a stranger into our group. And now this would be a young girl. Phyliss said she promised to show us all the pictures and delete any we were uncomfortable with. She said she would only post pictures on websites with our approval and keep the rest of the pictures in her private portfolio for artistic and erotica magazine editors to review for her future work opportunities. Again, none would ever be published without our consent. There would be no charges for her services. She even offered to do the session naked just to put us at ease and gain our trust in her, but we would have to agree not to touch her. She said she wanted to direct the photo shoot and would instruct us for posing and modeling.

I expressed my concern about being the oldest member of our group and how she would feel about that. Phyliss said she asked Pam about our ages, and Pam reassured her that we would all be treated with respect and older, mature crossdressers often make the best models and their pictures are highly desirable by both men and women. She said our session would be private just with her, and none of us needed to feel embarrassed or ashamed about our crossdressing. We all did love women, so the thought of a young nude woman taking pictures of us greatly excited us! We trusted Phyliss's judgement and if she decided we should do this we would all agree to it. Phyliss said Pam would provide a contact and we decided to let Phyliss act on it on our behalf and would agree to whatever she set up. Phyliss said she would make the arrangements with Pam, and she would set it up and let us know the date.

After our discussion, Phyliss had another porn video for us to watch. Phyliss told us to pair up and watch the video as "couples." She said, "I want us to feel like we are on a date, sitting close and watching a movie together." Robin immediately took my hand and led me to the edge of one of the beds and we sat down together, our bodies touching. Phyliss and Alice paired up on the love seat, but we could all see each other from where we sat. The video started with a young boyish looking sissy, dressed sweetly, standing in sexy lingerie, a short sheer, yellow nightie with matching see-thru panties. Nothing else. Just those two little skimpy articles of clothing to hide her body. She had a little girlish patch of hair just above her flaccid penis and small ball sack.

"Daddy," as she addressed him, a large older, burly man came into the room naked and sat down on a couch. He told the young sissy he called "Tina" to lay across his lap with her bottom up. There was no explanation why, but apparently Tina and Daddy enjoyed this type of pet-play, as Daddy pulled down Tina's panties and began spanking her! Tina whimpered and wiggled her bottom. Daddy toyed with her, smoothing his hand over her rump, and then smacking her bottom again. This went on for several minutes, repeating the spanking and soothing of Tina's buttocks. Daddy reached under and rearranged Tina's little, now hard penis to settle between Daddy's thighs. He told Tina to cum while he spanked her and Tina grunted, pushed her hips down into Daddy's thighs and came, almost immediately after hearing Daddy's instructions. This must have been a familiar scenario for Tina, as she quickly lifted herself off Daddy, kneeled in front of him and began to lick her own cum off Daddy's hairy thighs. Daddy was hard and pointing straight up, nearly twice as big as Tina's little penis.

These videos always excited us girls as we watched the action unfold. Robin told me to spread my legs and reached up under my dress to find my wet panties and hard dolly. Phyliss had her panties down around her ankles with her legs spread and Alice was playing with Phyliss's cock under her side-split dress. Alice was the only one who had ever experienced anything close to what we were watching when she had her ongoing relationship with Charles. I recalled her conversation about him during her interview.

Tina lapped up her cum and moved up to Daddy's balls and licking his big, thick cock. We could tell she was well-practiced and took most of Daddy, going down on him quickly without any gagging or hesitation. I was getting so hot, watching them, and feeling Robin's hand on my panty-covered dolly. Robin pushed me back on the bed, lifted my dress and took my panties off. Robin began masturbating me. It was feeling so good! Phyliss told Robin, "Kiss her dolly, Robin."

Robin held my balls, and I held the base of my dolly and pointed it up so Robin could kiss it. Robin leaned down to kiss my cockhead and lick along my shaft. I nearly begged Robin, "Please...please...suck me." Robin bobbed down on my dolly and sucked me into her mouth. She had no problem with my small penis and took me down to my base. I was getting my first sissy-suck job and loving it! No man or sissy had ever sucked me before, and now it was Robin, who so lovingly kisses me on my lips and now was sucking my dolly! Omg...

The movie was still playing but no one was paying any attention to it now. Phyliss and Alice focused their attention on the two of us, enjoying the sissy show we were providing for them. I felt wonderful with my dress pulled up, my panties off and still wearing my hose and heels while Robin sucked me in and out of her mouth and the other girls watched us. I felt the build-up in my balls and penis, and I jacked the base of my cock as Robin continued to mouth me. I called out, "Robin, I'm going to cum!" Robin held her mouth firmly over my dolly as I spurted into her mouth with 4 or 5 heavy squirts. She held me gently in her mouth until I began to soften and finally go limp. I looked over to see that Alice had masturbated Phyliss to completion and there was cum on her long, sexy, nylon-covered legs and thighs. We are all attracted to Phyliss's long, shapely, womanly legs encased in smooth nylons. I remembered my own excitement licking my own cum from her legs several weeks ago. I was simply in bliss now and my sissy feelings were flowing. I couldn't resist and simply asked if I could lick Phyliss's semen from her legs. She said, "Please. Come enjoy yourself Sissy! Suck up my cum."

I took her heels off and for some strange reason I just wanted to kiss her toes in those pretty nylon stockings. I gave a quick lick to her toes and then I took her panties off from her ankles so I could get a better angle to lick her legs. Alice had extracted quite a load from Phyliss and some cum had dribbled down to her calves. I began there as I looked up between her legs to see her cock and balls. As I worked my way up her legs I wondered if after such a short time she might be able to get hard again. Phyliss being nearly half my age, I remembered myself at that age and it usually didn't take long for a round two to occur. Phyliss was enjoying my oral attention to her legs and watched me swallow her cum as I licked my way up near the tops of her stockings. I decided to take a chance and licked her big, hairless balls, sucking each one gently into my mouth. Phyliss's cock twitched. I knew she wanted me to try.

Alice and Robin had taken off their dresses and panties and were sitting side by side on the bed masturbating each other as they watched me fellate Phyliss. I gently pulled and stretched her balls as I took her in my mouth and brought her semi-hard cock back to full rigidity with my mouthing. Alice and Robin made each other cum while watching me. I really was enjoying cock-sucking now, like I guess I always knew I would, and I liked seeing the pleasure I could bring to a man. I felt like a woman, giving head, and it was amazing. I wanted to bring Phyliss off again, in my mouth and suck down her cum. I loved kneeling between her spread legs. I wanted Phyliss to desire my mouth on her cock the way Robin loved to kiss me. She held the back of my head in place, grunted and bucked a load of her seed into my mouth.

On my drive home, I began thinking about Pam and doing our photo shoot. I was getting hard again...