The New Sissy Club Pt. 02

(It is recommended you read The New Sissy Club Part 1 first or this won't make much sense to you.)

After my first meeting with the "girls," Phyliss set up email and text chat groups for us to stay in touch and discuss any issues. During the week, at times I felt guilty over my behavior after that first Saturday with them, but then I knew I belonged here, with Phyliss and Robin, and I was a full participant now. I tried on new outfits that I could wear to meetings during the week. I bought several new panties, bras and stockings online and had them shipped to my home. I discreetly tried on shoes at my local Walmart to be certain they would fit. Not wanting to look conspicuous, I disguised my ladies shoe purchases among "manly items" in my cart.

I began to wonder if I had really been gay or a sissy all my life and now it was coming true. How could I love pussy and yet feel this way? I had never really been attracted to men in the past although I always admired a man with a nice hard cock in porn videos. I found myself jealous and envious of their size and ability to please a woman. My ex and former girlfriends never really complained about my size, but all of them admitted to me that I was "small" in comparison to other lovers they had been with. Still, I tried to convince myself I wasn't attracted to men since this was an all "girls" group....but who was I kidding? Phyliss and Robin definitely had cocks....and I had a "dolly." I still hadn't sucked cock yet, and I was a little envious of seeing Phyliss and Robin sucking each other last time. But I knew my time would be coming. Would I be ready for it? What if I don't do it very well? What if I gag? What if they laugh at me? I still secretly still longed to be a cocksucker for them both! And I wondered how I would feel if they ever sucked me.

Phyliss informed us via email that she had a new potential member for our group. One of the last rules for the group was that any new members would need to audition to maintain our privacy and insure we didn't get the wrong kind of "men" applying and just trying to infiltrate our group. Phyliss was always very protective for us. She said she was going to invite him Saturday to audition. We asked Phyliss how we were going to do this and keep our privacy? What would be involved with the audition? Would we still be dressed while he auditions?

Phyliss told us: "It will be no different from a regular meeting with a few small changes. We will arrive at our regular time, 11 am, and Alex (Alice) will come at noon, giving us time to all get dressed. I bought us all black veils from a costume shop that we can clip in our hair to protect our identities just until we are sure about Alice and none of us are familiar to her.

"As far as her audition goes, I wrote new audition rules that I sent to her as follows:

1. You must agree to all regular club rules.

2. You will bring and model two outfits for us. One will be ladylike, women's clothes. The other will be lingerie.

3. While wearing an outfit, or partial outfit, we will interview you.

4. You will be asked to complete a task of my (the superior in the group) choosing.

5. You will get dressed in your street clothes and leave. We will inform you of our decision within 24 hours.

She agreed to all the audition rules. Are we all agreed here?"

Robin and I both agreed to the rules.

The 3 of us all arrived around 11 am the following Saturday. We took turns using the bathroom to dress, mostly for make-up and hair. We could save time by just openly dressing in the room together. But it still seemed sexier to me to see the girls after they were dressed, rather than in the process. I still felt a bit of modesty, even after all I had been through last week, so I dressed on the side of the bed nearest the wall. Unless they were really trying to peek around the bed, they wouldn't really see me, and I wouldn't be looking at them. I brought a short bright pink skirt, a pink floral top, white stockings and garter, a white lacey bra and white heeled sandals. While in the bathroom, doing my wig and the little make-up I wore, I dabbed a bit of perfume down my crack. I tried adding some eye shadow today for the first time too. I finished with a pink lip gloss to match my clothes. Phyliss wore a navy-blue dress with black hosiery and Robin dressed in all red. We put the black veils on and set up chairs across from where Alice would be auditioning.

Alice arrived and was of a darker complexion, perhaps Indian or Pakistani, maybe Mexican, but she spoke perfect English. We must have looked rather strange to her with the three of us wearing those black veils. Phyliss introduced us and explained to her why we were wearing them.

Alice was about 5'5, very slender and her nearly black hair was pulled back in a ponytail. We all knew she wouldn't need a wig. Just let down that beautiful black hair. I was hopeful with her small frame and physique that I would perhaps no longer be the "smallest" in the group. Phyliss immediately took charge, as usual, and told Alice to go into the bathroom and change. Phyliss played another video for us while we waited for her. It was a Sissy Trainer. A woman explaining and teaching us how men should become sissies and cuckholds. She encouraged us to give up pussy for real men's cocks. I had that new tingly feeling I've been experiencing in my panties again.

Alice came out wearing a mostly purple, but multi-colored dress, closely matched lavender color shoes, 2" low heels and had let her hair down. She even managed to curl it a bit at the ends to make it flip up around her shoulders. Her make-up was nicely done. Lavender eye shadow, black mascara and eye liner and a deep purple lipstick. She even wore purple press-on long pointy nails! She was really quite exquisite!

Phyliss said, "Very nice, Alice! Are you wearing the required bra and panties under that lovely dress?"

Alice responded, "Yes, Ma'am."

"You can address me as Head Mistress, just for today, since I'm leading our group today. It has a bit of a double meaning as well."

Without hesitation Alice responded, "Yes, Head Mistress, whatever you prefer."

"We'd like to see your undergarments, now, dear. Show us your panties and bra. Robin, please go over and help unzip her and get her out of her dress for us."

Robin helped unzip her and she stepped out of her dress. Beautiful lavender panties and bra. Big dark brown areolas peeked out over her push-up half bra. I thought I noticed a few long black hairs around her nipples, but I couldn't see them completely. Stay-up thigh-high taupe stockings. We could see the outline of her semi-erect penis through her panties and what appeared to be very dark pubic hair! I was glad no one could see me blushing behind my veil. She really looked pretty! A very unique sissy girl, especially compared to me!

Phyliss said, "Good girl, Alice. Turn around and face the wall, Sweetie. Take down your panties...not all the way off, just to your thighs, Hon. Now bend over and spread open your bottom for us."

I was shocked that Phyliss told Alice to do this! But Alice didn't hesitate. She turned and faced the wall and pulled her panties down to mid-thigh. When she bent over and spread her cheeks, my dolly (since Phyliss called it that, I began using the name myself; it just seemed appropriate for me. I had a little dolly, and I was going to try not to feel ashamed about that) was so stiff in my panties, looking at those beautiful purple nails against her dark brown skin pulling her ass cheeks apart while we all watched. I was beside myself when Phyliss told Robin to go up and smell her anus to make sure she was clean, as our club rules state.

Satisfied, Phyliss told her, "Very nice. Now turn and face us, hands at your sides so we can interview you properly."

I immediately thought to myself I'm glad they didn't have me audition this way! I don't think I could have done it! I was feeling embarrassed for Alice yet feeling very aroused. That tingly feeling in my panties was growing stronger. I liked feeling that way now! Pre-cum leaked into my panties.

As she turned to face us, her cock sprang out jutting and bobbing in front of her. But it---she---was different. She was uncut and had a foreskin! We were all circumcised. I'd never seen a male in person like Alice. I was fixated on her cock! My jaw dropped. Her legs and body appeared to be hairless, but she had an incredible big, black, short curly-haired bush surrounding her petite, slender cock. It was trimmed neatly but there was a lot of hair! It was not unflattering at all. It looked normal and natural on her....like a woman's bush! She was truly magnificent; so feminine looking! Her cock was semi-hard and pointing out, bobbing up and down, pointing towards us. It looked long, maybe between 5 and 6", longer than my 4" dolly, but it was slender, like the girth of a thin carrot, and veiny with slight curves in it. Her balls were almost tiny looking and withdrawn, snuggled up tightly under her penis. But I was so attracted to her whole package between her legs!

Phyliss looked Alice up and down and then stated, "Alice, we have no shame here. I'm glad to see you have no problem following instructions. I know you feel vulnerable and exposed right now, but we feel it's the best way for you to be honest with us, and the best way for us to interview you like this. You cannot hide how your penis reacts when your panties are down, and we will want to see that. I see you're already excited. I know you've read all the rules, Alice, and agreed to them. So now, tell us about yourself."

Alice told us, "I'm 34, never married. I've always felt different from other boys and fashioned myself as more of a girl...or a girly-boy. I liked art classes and dancing growing up. I love to dress in feminine clothes and my crossdressing began when I tried on some of my older sister's clothes at a young age. I started buying my own clothes after that, hiding them, and my secrets."

"What did you like about your sisters' clothes, Alice?"

"The feel. The look of them. The textures. The fabrics. The softness. Especially her panties, slips and bras."

Next, Phyliss asked, "Have you been with any men before?"

"Just one," Alice said. "I acted as a housewife for an older neighbor gentleman, Charles, for about a year. He was 72, widowed and had seen me dressed in my home from his bedroom window. He invited me over to talk about it and he said we could both get what we want if I agreed to be his housewife in the evenings and on Saturdays. I had a key and would go over after work, dress and live out the nights as his housewife. He would always be nude when I arrived to tease me. His big cock and balls hung low and would swing between his legs. He didn't shave so he was very hairy, even his balls. He liked me to rub my face in his graying-hairy bush.

"He was a little overweight but for an older man, he was very virile and always horny. I loved looking at his cock and touching it. I would do a small list of chores when I arrived that he had ready for me to do. On various days I would cook, clean, vacuum, dust, change his bed, even clean his toilets. He loved it and when I finished my chores, he would reward me with his cock at the end of my nightly visits. He taught me how to give him a hand job and blowjob. How to suck his cock. He taught me to accept his cum and I learned how to swallow it. He said cumming in my mouth always helped him sleep at night after I left. He loved that I swallowed his loads. He said his wife never did that. Sucking him helped me sleep too. It put my mind at ease, and I felt peaceful and tranquil. His manly ways, big cock and balls were good for me. But he never touched me though and said he never wanted to see me naked. He said he wasn't gay like that."

"So how did you receive any relief?"

"When I got too horny or frisky, he would usually take me over his lap and pull my panties down and spank me. He would put a towel on his lap and allow me to cum like that while he spanked me. At times, he would also have me put on a condom and bend me over the kitchen table, pull my panties down and spank me until I came. Sometimes he spanked me so hard that I wouldn't ask about an orgasm again for weeks. It taught me to respect him and his needs and not my own. I learned to be a sissy with him. He taught me what it meant to be a sissy. He spanked me for my own good. He also bought most of my clothes for me. He really liked to see me in nylons and heels prancing around his house. I liked that too."

"Obviously, this was a very exciting time in your life, yet you say he never played with you. Were you allowed to masturbate?"

"No. Never. He said that wasn't ladylike. He said I should learn to cum just from sucking his cock."

"Were you ever naked with him?"

"Oh, no, Head Mistress. He never wanted to see me naked. I would only wear girly, feminine clothes in his home. He said he wanted a feminine housewife, not a naked little boy in his house. But I did often wear G-string thong panties while doing chores. And he always wanted me to take my dress off during his pleasuring time. Just be in my bra, panties, hose and heels. But I would often cum in my panties just from pleasuring Charles."

"What was the most humiliating or embarrassing thing you ever had to do with Charles?"

"Charles was never really mean to me but, of course, I did consider him a very dominant man. But he did have one sort-of game he liked to play with me. He sometimes made me wear a diaper and an adult bib. The bib had the word 'SISSY' printed on it in big letters. He said he ordered it special for me. That's all I had on. Then he would sit at the kitchen table with his chair turned out and place a towel on the floor. He would coat his thick cock and hairy balls with honey, dangle them over the edge of the chair, and I had to crawl over to him on the floor and kneel between his legs and lick it all off. He would always reward me with a huge load of his thick cum."

"And how did that make you feel?"

"He would never laugh at me while doing this, but it was the most humiliated I ever felt with Charles. But he really enjoyed it...seeing me like that...and doing it that way for him. It was humiliating and embarrassing for me, but I never objected and found myself even asking him a few times if we could play the game. He said he was proud of his little sissy housewife for asking. I was always hard and wet in my diaper when we played this game. Sometimes I would even cum."

"Thanks for your honesty, Alice. So, you have never been naked or exposed, like you are now, in front of anyone, man or woman?"

"No, Head Mistress. This is the first time."

"And how do you feel right now?"

"I didn't realize how intense this audition would be. I didn't know the level of questions I would be asked. It's embarrassing for me to be standing in front of you all like this, answering these questions, but you can see my obvious excitement. I'm relieved to finally expose myself. It's nice to be with other sissies who understand. My boner feels so good right now. I'm getting so hard."

"Why are you getting so nervous and stressed? You've done well so far."

"I'm used to wearing panties. Not pulling them down to expose myself and stand like this. It's very humbling, Mistress...I mean Head Mistress."

"Would you like to stroke yourself while we finish this interview? To help you relax more?"

"Oh, yes. Please. May I?"

"Yes, but slowly. I don't want you to orgasm. Just use your thumb and index finger. Up and down."

Alice started to stroke herself. She moaned slightly. Her two fingers, with those long-painted nails, glided lightly over her unusual slender cock. Her tight little balls pulled up with every stroke. I was mesmerized just watching her.

Phyliss asked her, "Is that better? Is that helping you relax a bit? You don't ever have to feel ashamed to masturbate here with us. Carly was embarrassed but she masturbated for us last week. You look lovely and so sexy like this, Alice. Just enjoy it. It's almost over."

"Yes," Alice said. "I've never touched myself or done anything like this before in front of anyone."

Phyliss praised her "Good," and then asked, "Now tell us why it ended with Charles, Alice?"

"He sold his house and moved of state to live with his daughter. He emails me often and tells me how much he misses our time together. He said I gave him more blowjobs in a year than his wife gave him in over 40 years of marriage. He says his cock and balls miss my mouth. He encourages me to stay celibate and never have sexual intercourse with a woman."

"Have you ever kissed a man, Alice?"

"I never kissed Charles. But once, in a gay bar, I flirted with a handsome older man in a booth. I unzipped my pants and showed him my panties. I made out with him, and we kissed while I fondled him through his pants under the table. While we were kissing, I made him cum in his pants."

Phyliss continued questioning Alice while she stroked her penis. "Have you ever been with women?"

"Yes, but I've never had intercourse. I've never been in a woman's pussy. I used to answer ads for women seeking oral pussy worship---and oral only. They were mostly older, lonely women, sexually frustrated. I preferred larger, chubby women...calling themselves BBW. That means Big Beautiful Woman. The hairier they were the better for me. The only thing I asked of them was to allow me to wear their worn panties while I performed oral on them. I serviced two women on a fairly regular basis. I stopped seeing the women only after I met Charles. He didn't want me involved with anyone else if he took me as his housewife. The girls were disappointed that I wouldn't be their little oral pet anymore. Charles said he would reward me with his cock often, and that's all I would ever need."

Next, Phyliss asked Alice, "Why do you want to join our club?"

"The only time I have ever truly felt free to be a sissy was with Charles. Charles helped me understand who I am...that I'm a sissy. I've always had to hide it from others. I hope this can be a freeing and safe experience among other like-minded men...I mean, girls like us."

Phyliss looked at me and said, "Carly, you seem fascinated with Alice's stories and her cock. Is your dolly tingly? I see she's leaking a bit. Why don't you go over and help her? Take your veil off. She has a little different cock from ours. Take your fingers and gently draw down her foreskin so her knob pops out completely from the shaft skin. It's like a clitoris hood. You have a little dolly. Alice has a clitoris cock. Then lick those pearly beads dripping down her shaft and around the tip of her clitoris. Go ahead, don't be shy, Carly. Kiss her cock. Kiss her clitoris. Your first taste of cock and cum. Swirl your tongue around her cockhead. Stick the tip of your tongue into her little pee hole. Stroke her shaft tenderly and try to draw up a more pre-cum. You're such a special Sissy, Carly, helping our new friend like that."

Omg...I don't know if it was Phyliss's talking to me like that or the excitement of touching my real first men's cock, licking it, his tip...her tip...rubbing his...her... thin shaft and slippery foreskin, seeing her with that big bush surrounding her cock, but I was flooded with excitement. I started to buckle at my knees, wobbling on my heels, bending over, and trying to squeeze my thighs tight together, but I couldn't stop it. I couldn't hold back. I tried to keep it quiet and muffled a low grunt. I came in my panties. I was totally embarrassed.

Phyliss knew what happened and so did Alice. To embarrass me further, Phyliss said to me, "Carly are you wet? Have you done something naughty? Did you wet your panties, Carly? Did your little dolly spurt? Did you cum just from kissing Alice's pretty clitoris she-boy cock?" She knew I did. I had no choice except to answer. "Yes, I came in my panties. I'm so sorry. I couldn't hold it. I got so tingly and excited."