The New Sissy Club Pt. 05

Phyliss informed us by email that Pam, the photographer, would be coming to our next meeting. We are to arrive an hour early to dress and be ready for her arrival. Phyliss said we could interview her and ask any questions before we begin. As the oldest sissy, I was nervous but excited for this new experience. I wanted to look my best and looked for outfits that might flatter my chubby body. I took extra care the night before and shaved twice, just to get all the hair shaved off and as close as possible. Even at my age, looking in the mirror at my hairless body and genitals made me feel younger and excited. I decided on a royal blue flare skirt, with flowers on it, a white top and white lace bra, white garter belt with taupe nylons and white pumps with 3" heels. I accented the outfit with a pearl necklace and matching pearl earrings. It was an old-fashioned look, but I am the oldest in the group anyway so I thought it would be an appropriate look. I used a brown, shaggy cut wig. I did minimal make-up, blue eye shadow, eye liner, mascara and burgundy lipstick.

When Pam arrived and knocked on the door, we all got a little more nervous, wondering how she would react to seeing four cross-dressed men in the same room. I mean, we all knew she knew what she was coming for and probably what to expect, but this was something none of us had ever experienced. A young girl with four older crossdressers and we knew we would be at least partially exposing ourselves to her. She did promise to work naked and that made me a little more at ease.

Phyliss answered the door and introduced herself. She was pleasant, smiled and shook her hand. All the girls looked great! She brought in her equipment, tripods, cameras, film bag, extra lights, etc. As she looked around the room Phyliss introduced us by our fem names, and she shook everyone's hand showing no signs of being shocked or surprised by our appearance. She said, "I'm so glad you accepted my offer and invited me to do this photo shoot with all of you. I understand you all may have some questions for me before we get started?"

Phyliss started the questions and we all added in our own. "I've told the girls everything we discussed in our correspondence but please reassure us that nothing will be published or posted without our permission."

"That's right. I'm building my own portfolio to work with art and erotica publishers, and I also want to do this for all of you. Crossdressers and sissies are highly sought after in pictures and on the Internet and highly desirable on fetish and dating websites, if any of you may be looking for partners---either male or female."

I asked if she could explain a little more about that.

"Sure. For example, I'm currently working with a publisher on older males who have become feminized, submissive and even cuckolds for their younger wives. Some do this voluntarily and others do it out of necessity---for their wives' or female partners. There are many women and men who enjoy a sissy partner. They are more docile, attentive and obedient. Some men are trained to be sissies by their partner, to suit their own tastes and lifestyle. Mature women usually want less penetration, or none at all, and more oral---both vaginal and anal. They often prefer toys to their husband's penis. That's not acceptable to most alpha males but a sissy can be trained for that type of service to the woman. The sissy often masturbates replacing sex with his wife. The article and accompanying pictures won't be to embarrass or humiliate the males, but rather portray how a marriage can be saved with a change in lifestyle. Many married women have a very rewarding and fulfilling marriage and sex life with sissy husbands. The story and accompanying pictures will explain many reasons males become sissies. Some just desire it and feel more feminine than masculine. Some are househusbands who take on more traditionally female roles at home, or that of a housewife, and dress accordingly. Essentially, they become sissies at home and wife finds she can assign her sissy household chores, cooking and cleaning, laundry duties and the like, and the sissy makes her life easier.

Some older males experience ED or impotence issues and leaves them feeling emasculated and turn to more feminine ways. The wife may cuckhold the husband at this point to save their marriage. And the sissy often becomes a participant in his wife's lovemaking with other males. By oral pleasuring her and even pleasuring her male lovers. To be blunt, the sissy prepares the male's cock for his wife---by sucking his penis. A sissy may be able to enjoy watching his wife have sex with a lover. A sissy can also replace wifely duties for a male, making his mouth and rectum available for his male partner. A good sissy can learn to enjoy cocksucking and being taken anally more than intercourse with his wife. Some sissies just want a dominant in their life, be it male or female, a more powerful figure of authority, to control and guide them. And of course, some crossdressers just enjoy the lifestyle, wearing softer, feminine clothes that feel good against their bodies, giving up masculine ways, and may want to explore more bi and gay experiences together. From what Phyliss has told me, the last one applies to all of you here, and why Phyliss started 'The Sissy Club.' I want those type of pictures from you all."

Pam was exciting me, just by her explanation, and I was already experiencing the tingly feeling in my panties.

Phyliss said, "If there are no further questions, I guess we're ready to get started. Pam, you said you would work in the nude. If you're ready, I think the girls are ready. Please take your clothes off."

Pam had offered to be naked, as a way of trusting her and putting us more at ease, so she had no resistance to Phyliss's request that she disrobe. Pam had a young, pretty, face, dark brown, long hair and black glasses. She posed no objections to undressing. Alice took her clothes from her as she undressed and took them to the closet to hang them up. I watched Alice smell her panties as he walked away with her clothes. When she was nude, my dolly twitched in my panties. I hadn't seen a naked woman in person in quite a long time, maybe a few years, and never a young girl like this, unless you count my college dating years! So long ago that I couldn't even remember what young girls looked like in person! Pam had lovely grapefruit sized breasts with large puffy nipples, that hung down perfectly, and a lovely, full, overgrown, non-trimmed hairy, brown bush between her legs. Honestly, I thought she looked amazing! Quite a contrast from all of our shaved bodies and genitals. Even more surprising, Pam told us, "You can see I'm not exactly a traditional female. I don't shave my pussy and I don't shave armpits either," as she raised her arms to show us her beautiful hairy armpits.

She said, "If you are all satisfied about my sincerity, then let's begin. I want you all to trust me and just do as I tell you. I know the kind of pictures I'm looking for and what publishers and the Internet want. I won't be curbing my language and I will be directing you to do some things that may embarrass you, especially in front of me and my camera. That is not my intent, but it is necessary to get the kind of photographs I need for my work. Please just follow my instructions so we can move quickly through this first session. Sometimes I need to take several shots so if I tell you to 'hold it', it means to stay in that position until I give the next instruction. Sometimes I want you try to forget that I'm here, naked with you and taking your picture. Just act natural. From what Phyliss has told me, you'll be doing things that can be considered normal activities for your regular group meetings. Except I'll be photographing it. Some things will be new to you, but I know what the publishers are expecting, and I want to deliver them the right product. I'm going to be calling out commands quickly sometimes and click quick pics. Just follow my directions and everything will run smoothly."

I thought to myself about her words and this being the "first session." Did that mean there would be more? What was she expecting us to do for this session? I was getting chills, but good chills, the kind that make my dolly tingle and leak.

Pam called us up one by one for individual shots first. We were fully dressed to start, and she posed us in various positions, leg out or forward, hands on hips, looking back over the shoulder, etc. Next, she said to each of us, one at a time, "Skirt up and hold it. I want to see panties."

When it was my turn, she saw I was wearing a garter belt and told me, "Skirt up and adjust your garter strap. Good. Now hold that." She followed by saying to each of us individually, "Panties down, just to thighs. Turn sideways to show your erection."

I was nervous about my ED issues but I wasn't having any problem today staying hard. I wasn't expecting this today. I was thinking maybe just some casual shots of us girls in dresses and skirts and maybe a few panty pics. I was aroused by every instruction and command that Pam called out to us.

"Now let's take your dresses and skirts off, leave your panties down where they are and pose like a shy girl, hands over your cocks, covering yourselves."

We all followed Pam's directions as she called them out. "Knees together. Bend forward. Cover your genitals. You're a shy sissy posing for your picture taken. Bra off and cover your breasts with one arm across your chest."

It was though she was directing a movie and we just followed her directions. She never asked us "please." We were just expected to do whatever she said. Looking at our naked director made it easier for all of us to follow instructions. Several times I found myself staring at her very hairy bush!

"Good. Bras back on. Now panties at your ankles, hands on your hips and push your pelvis forward. Turn sideways."

Her commands continued to get more embarrassing. "Hold your penis. Pull forward and hold it. Now all the way back and hold it."

"Let's shoot that again. Stay sideways. Forward stroke and hold it. Now back and hold it."

My dolly was leaking. Several strands dropped to the floor. Repeating that action felt like torturingly slow masturbation...without release. She made all of us do that twice. She knew how to tease us as well as take photo's!

She then told us to turn around with our backs to her. "Bend forward. Hold your ass cheeks open. Hold it."

It was the first time she offered any explanation for the pictures she wanted. "Men especially like seeing the sissies ass and what she has to offer him back there."

After we finished these individual embarrassing shots, she had us put our panties back on and remain in our undergarments; bras, stockings, garters for those of us wearing garter belts (myself and Phyliss---with her exceptionally beautiful long legs) panties, and our heels. Pam started doing some group shots. We posed with legs out, Can-Can/Rockettes style and some forward shots.

"All of you turn around with your bottoms towards me. Put your hand inside the sissy's panties of the one next to you."

It felt nice to touch another man's ass. I put my hand down Phyliss's and Alice panty and they both had a hand inside mine.

"Good. Face me again."

All of us had wet spots on our panties and Pam took several shots of that before her next command: "Panties down in front on thighs."

"Good. Nice hard penises. Reach under and cup each other's balls. Hold right there."

Standing between Phyliss and Alice, I cupped Phyliss and Alice cupped mine. Phyliss cupped Robin and Alice held her own tiny balls. Pam took a series of shots with us standing this way. Everyone had a boner.

Next, she wanted two of us together. She said the contrast between the largest and smallest cocks would make for some great pictures, so she had me and Robin come up. She called out, "Face each other, panties down to thighs and hold it."

"In closer together. Cocks touching."

Phyliss interrupted. "Carly is the smallest among us. Hers is a dolly. Please refer to hers that way."

"Hold your penises---Carly, your dolly---and touch your cockheads together. Perfect. Stay like that but lean in and kiss each other."

Omg...she had no idea how much Robin and I love to kiss! Holding our kiss would make it even better for the camera shots. So, we kissed, Frenching, but holding our mouths tight together. My dolly touching Robin's almost made me cum, and in a way, I was relieved when she called out for the next pose so that I wouldn't have a rather embarrassing accident. But what Pam said next embarrassed me even more!

"Good. Now Carly, go over to the bed and bend over, palms down on the bed. Panties still on but a little lower, around your knees. Robin, take your panties off and stand directly behind Carly. Place your cockhead between Carly's cheeks and hold it. Now hold that position and put your hands on Carly's hips."

Robin's cockhead was pressed right up against my anus! Phyliss had told Pam our group hadn't done anal yet, except for oral anal, and Pam only made Robin simulate that action. Phyliss told her "yet?" What did that mean? Pam came around the side of the bed to film my underside, my dolly poking out in front, while Robin held my hips with his cockhead pressed into my ass. I was hot as hell! My dolly was dripping strands of pre-cum!

Pam said "Girls, all panties up. I want all four of you for this next series of shots. Carly and Alice, go freshen up your lipstick."

When we came back from the bathroom, Pam continued, "I'm going to do wide angle. Phyliss and Robin back-to-back. Carly and Alice on your knees in front of Phyliss and Robin, sideways from me." Phyliss moved in front of me, and Robin went to Alice. "Carly and Alice, hands on the waistbands of your partners panties and hold them there. Begin taking down their panties, just exposing the head of their cocks and hold it there."

"Great! Now pull your own panties down and pull your partner's panties down to their thighs."

"Good. Now I want to see dominants holding your cocks up and sissies licking their balls. I want to see tongues out. Sissy subs, bring their balls forward with your hand. Lick their balls. Hold that."

"Now tops, point your cocks towards your sissies' mouth and hold it."

"Tongues on your partner's pee hole and hold it!"

"Carly and Alice, I want to see lipstick imprints on your partner's crotch, just above their penises, on the nice shaved smooth skin."

"Very good!"

"Two bottom sissy submissives start sucking your dominant's cock. Just your mouths over the tips. Hold that."

Pam didn't hold back on her directions. But every order she barked out seemed to make us all even hotter and hornier. I'd never thought of us in those terms but apparently Pam saw us that way, at least for these pictures. "Bottom sissy submissive." I liked that. A lot. And to suck my "dominants cock." Mmm... It seemed like Pam knew me personally. She picked Alice and I for the sub positions. We were both perfect for this, Robin and Phyliss having the much larger cocks. I'm sure Pam picked us that way when she saw our sizes.

"Sissy subs, suck their cocks about halfway. Get it nice and comfortable in your mouth and hold it. If anyone feels like they are going to cum, we'll stop and take a little break. Are we all good here?"

Both Phyliss and Robin groaned at the same time as we took them in our mouths. Alice and I were in no position to give an answer, but Phyliss said, "I think everyone is fine. Let's continue."

I took Phyliss about halfway to her base, maybe a little more. I'd sucked Phyliss before, so her cock size wasn't a surprise to me. Alice was probably the most experienced cocksucker being with Charles for a year. She didn't have much problem sucking Robin's cock, despite her huge size. Alice must have eased Robin's cock partially into her throat. I wished I could do that.

"Subs, hold your penises. Keep sucking your partner. No in and out. Just hold it in your mouth."

"That's good. Hold that. Turn a little more towards me."

Pam moved in for close-ups of our mouths stuffed with the girls' cocks.

We were so worked up and hot that Phyliss started to push in my mouth, then stopped and said to Pam, "We need a break and I hope you understand, but we all need to release. We need to cum. All my girls are overly excited right now. We all can't stay hard like this while we're dripping pre-cum and ready to ejaculate. We can continue this at another session."

Pam said, "I want some cum shots. I'm sure you knew I would."

"Yes, I suppose I did," said Phyliss.

"I said there could be no touching of me, but since these pictures are for both men and women, I want to show how a sissy can still enjoy sex his wife's body without intercourse. Each of you can jack-off on different parts of my body without touching me. One on my pussy, one on my tits and one on my feet and toes. The last one can jack-off on my hairy armpit. I'll use my remote clicker to capture pictures. Give me a minute to set up my camera."

We were all a bit shocked the way Pam had just taken over our group, but no one objected, and we all couldn't have been any more turned on. We were all going to be face-to-face so to speak (face to pussy/tits/feet/armpit) with this young, nubile, student photographer and jacking-off while she captured our cumming on her rolls of film.

Pam sat in one of the oversized chairs and said, "Panties around your ankles, girls. Biggest to smallest, in the order I said. Robin, you get my pussy. Kneel."

Omg...this was exciting! Watching my sissy friends masturbating to a woman's body. Pam held her hairy pussy open, and we got a good look inside. She was definitely wet! Robin, of course, had the best close-up view and stood when he was ready to cum. It was less than a minute as he pointed his erection at Pam's pussy and splashed his semen on her hairy mound. Phyliss was next and stood over her chair aiming his cock directly towards Pam's beautiful, round tits. She held them together as Phyliss shot gooey globs on her globes. Cum was dripping from Pam's pussy and tits as Alice kneeled in front of Pam's pretty feet, her toenails painted deep red. Alice's slender clitty-cock slid quickly back and forth in her hand as she too spilled her sperm quickly on Pam's toes. My dolly was thicker than Alice but shorter, so I was last.

Pam slumped down in the chair and raised her arm up over her head. She stroked the hairs under her armpit with her fingers, teasing me towards her. She had a solemn look on her face and I just stepped up quickly, near her armpit and aimed my dolly towards it. I almost imagined her armpit as a pussy with the hair around it and after watching my 3 sissy friends soak Pam's body with their cum, it was barely a few strokes, and I was cumming on Pam's armpit.

Pam went straight to the bathroom and turned on the shower. She popped her head back out of the bathroom before she got in the shower. "We'll do lingerie at our next shoot. I want painted fingernails and toes from everyone."