Confessions of a Sissy

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by Wee Willie Winkle (edited)

I suppose this memoir might be entitled the confessions of a small cock sissy. I grew up the youngest of four children, with three older sisters. I suspect that I was an “ooops baby” or unplanned since my sisters are 9, 12, and 15 years older than me. I never really knew my father. He left my mother and us when I was about three years old. Mom never remarried and did her best to raise us on her own. As you can see I grew up in a very female centered household.

Thinking back I have to admit there were advantages to being the baby of the family and the only boy. Even though mom worked a lot to support her family I never lacked for attention. Much of that attention was given to me by my sisters, as I was often left in their care, especially my oldest sister Maggie. She was very much like a second mother to me. I suppose to the girls I was almost like a living doll, albeit one that needed to be bathed, clothed, fed, and entertained. And yes having my diapers changed and being potty trained by the girls as well as mom. I know it took me a while to figure out that guys could stand when they pee too, lol.

I grew up in a world of dolls and dollhouses, bras and panties, hair curlers and make-up, in fact all things girly. I suppose it is no wonder that my masculinity was tamped down at an early age and my feminine or softer nature encouraged to develop. As Maggie and my next oldest sisters Janice and Rachel like to remind me they would sometimes even dress me as their “little sister”. Lol, no wonder I like wearing panties even to this day.

My upbringing undoubtedly had a lot to do with my ultimate “sissification”. Not that I see that necessarily as a bad thing. Another major influence is the fact that I have a small penis and almond sized rather than walnut sized balls as well. On my best day I probably top out at about 3 1/2 inches fully erect. When soft I’m probably an inch and a half. Not exactly built to be a super stud. Thankfully that was never anything I wanted to be anyway. I have a much more submissive nature and am more than willing to let the ladies and as it turns out sometimes the gentlemen lead the way.

I have discovered that I am much happier and contented when I am in the company of an older take charge lady. Lol, think it has anything to do with growing up in a house full of older females? I did try dating girls my own age for a while, but most of those relationships bordered on the disastrous. Not only did it become readily apparent to the girls I dated how undersized my package is but I’m embarrassed to admit that I also have an issue with P E or premature ejaculation.

So not only were my erections lacking in stature but duration as well. Most of the time I would end up squirting during foreplay or at the first moment of vaginal contact. I know it had to be very frustrating for the few girls I dated. And a couple of them were not shy about telling me how disappointed they were with my “shortcomings”. Not surprisingly I soon became very self conscious around girls and hesitant to get involved in a relationship.

Things began to change for me in college. I got involved in the theater. It was there that I met the woman who would set me on the path I was probably always destined to travel. Ms. Arlene was in charge of set design in the theater department. Being much too shy to ever go on stage that is where I found my niche too as her assistant, protege, and gofer. Ms. Arlene was in her mid 40’s while I was just entering my 20’s. While not model thin pretty she had what could be described as rugged outdoors type good looks.

Tall with short cropped blonde hair and striking green eyes she was an imposing woman at about 5’8″ and 175 lbs, both taller and heavier than myself. I found myself rather in awe of her. She had the powerful arms and shoulders of a swimmer and the muscled thighs and buttocks of a woman who appeared to work out on a regular basis, and absolutely magnificent breasts that always seemed to be straining against the material of whatever she was wearing at the time.

I had been working with her for about three months when unexpectedly our relationship took a sudden twist one night. We were working late one evening finishing a set that was going to be used in a production the following week. Everyone else had gone home about 7 o’clock and I enthusiastically accepted her request to stay and help her complete the project. I’m sure that after three months she had a pretty good read on my personality and knew that not only was I submissive but likely a sissy pantyboy as well.

This was the first time we had actually spent time alone together and as we worked on the set Ms. Arlene began to ask me questions to get better acquainted she said. At first the questions were innocent enough covering topics like music and television. When she asked about girlfriends I had to admit that I wasn’t dating. When she asked why, I couldn’t come up with a good answer, or at least a truthful one I wanted to share with her.

She asked if it was because I liked boys and assured me that if that was the case it was perfectly OK, and that there were lots of “homosexual men” in the theater. OMG, Ms. Arlene thought I was gay. I was so embarrassed and flustered I stammeringly assured her that I liked girls just fine and wasn’t the least bit interested in men. Although that wasn’t entirely true since I had masturbated to gay porn before. But I wasn’t going to tell her that.

Ms. Arlene told me there was no need to be embarrassed that a lot of young people my age were still figuring out their sexuality and sexual boundaries. My face must have gone crimson when she informed me that she had seen me checking out her boobs and ass when I thought she wasn’t looking. She asked if I liked what I saw. Instinctively I denied that I had ever looked at her body. “Then you must like boys”, she accused, “…because I know real men find me attractive. Or is it that you think I’m too old?”

I was so confused I didn’t know what to say. I found myself blurting out the truth, “No, I think you are beautiful”.

A look of triuumph flashed briefly across her face before she sternly inquired “So that explains why you are parading around in front of me with an erection?”

Oh shit. It was true. All her talk of sexuality and just being so close to the woman I admired so had given me a mini boner that my loose fitting gym shorts and cotton panties weren’t doing much to contain. I was so humiliated, even though I had never consciously intended become aroused, much less show my arousal.

“You do realize it’s rude to display your erect penis to ladies don’t you?” she chastised me. “What would your mother think if she knew you liked to strut around like a little rooster showing off your cock?” she continued. “Would you like me to call her and tell her?” she asked.

I was both shocked and humiliated. Ms. Arlene had actually referred to my penis as a “cock” and shamed me by accusing me of intentionally exposing myself to her. And lord no, I wouldn’t want my mother to think I would do such a thing. Although I do recall when I would get the occasional erection in front of my sisters growing up mom was usaully my defender. The girls would tease me about it although I think they secretly enjoyed seeing it especially since I had the only penis in the house. Mom would tell them not to pick on me, that sometimes boys would react that way to certain things. I wasn’t sure she would spring so readily to my defense now that I was grown up especially since Ms. Arlene seemed to think I was intentionally “strutting my stuff” in front of her.

I was almost at the point of tears. “I’m so sorry, please don’t tell my mother. I didn’t mean to do it. It will never happen again. I promise.”

I shamefacedly entreated the stern faced Ms. Arlene. “Tell me exactly what it is you’re sorry for, dear,” she said in a softer tone.

“I’m sorry I was was rude.”

“And how were you rude?” she continued.

It was obvious she wasn’t going to let me off the hook too easily. “I was rude for having an erection,” I confessed.

“Not just for having an erection,” she corrected, “…but for practically waving it in my face. Is that what you meant to do, stick your hard little cock in my face?”

OMG there was that word again. I felt even more ashamed to have her refer to my penis as a cock. “No Ma’am,” I whimpered.

“I’m not so sure,” she challenged. “I can plainly see that you’re still erect.”

And it was true my little hardon had not diminished at all even through all my shame and embarrassment.

Ms. Arlene took a seat in a straight backed chair that was one of the stage props. “Come here,” she ordered signaling me to stand in front of her. “Closer,” she demanded as I took my place about three feet in front of her. I stepped toward her until our knees were practically touching. Before I even had a chance to react she reached out and grabbing the waistband of my gym shorts and underlying panties with both hands she skinned them down to my knees in one swift motion.

My breath caught in my throat I was so surprised. Instinctively I tried to cover my shame with my hands. “Hands at your side, mister,” she commanded.

I did as I was told.

She was clearly in control now. I saw the briefest of smiles cross her lips as her eyes focused on my mini erection before she became stern faced once again. “Is that what you wanted me to see, your hard little cock?” she questioned.

I was in shock and didn’t know what to say. Fortunately the question was apparently rhetorical and did not require an answer.

“It’s obvious to me young man, what a big part of your problem is with girls,” Ms. Arlene cooly informed me as she studied my slender 3 inch manhood. “You know if I were a guy and hung as small as you I don’t think I would be so anxious to be exposing myself to the ladies,” she went on. “Most women prefer a man with some meat between his legs. Have you had ‘size issues’ with your girlfriends?” she inquired.

Unable to look her in the eyes I admitted that I had.

“And panties too?” she remarked glancing down at the pink floral print panties now bunched between my knees. “I suspected as much.”

I dropped my eyes in shame. They opened wide again, however, when she surprised me by reaching between my legs and cradlied my tight little scrotum in her fingertips. “Small underneath too,” she remarked to herself as much as to me. I must have flinced when she touched me because she told me “Relax and I won’t hurt you.”

Did that mean she would hurt me if I didn’t relax?? I did my best to relax.

Continuing to caress my little pink ball sac with one hand she reached out and grasped my penis with the other. With her fingers curled around my little dicklette she began to gently stoke the tender underside with her thumb. My shame was complete when I almost instantly began to squirt semen in her direction. I felt weak at the kness I came so hard. Most of my cum landed harmlessly on the floor or dripped on myself but some sprayed as far as her lap and landed on her jeans. “Ho!” she half chuckled, “A minuteman too. I think I understand the rest of your problem with women.”

As my senses and strength began to return to me I heard her say, “You produce quite a bit of ‘baby batter’ for being so small, but you should never cum on a woman without her permission, and certainly not the instant she touches you.” With that she reached out and soundly smacked my bare bottom with her hand. “Do I make myself clear?” she demanded spanking the other ass cheek.

“Yes ma’am, perfectly,” I replied.

“And not a word of this to anyone,” she cautioned laying another whallop on my exposed bottom. “Understood?” She applied another firm smack on my reddening derrière.

Not responding quickly enough I found myself the recepient of two more well placed blows to my backside. “Yes ma’am,” I replied quickly this time.

“You will find yourself in a world of trouble,” she cautioned “…if you disappoint me.”

I had no intention of disappointing her. To be honest I was a little bit afraid of her but also I think falling in love with her. “Now pull up your panties and go home,” she ordered taking the opportunity to give my bottom another whack as I bent over to do as ordered. “Tomorrow is Saturday. I’ll expect to see you here at 9 AM so we can continue our conversation. Do you have a problem with that?”

“No problem, Ms. Arlene. I’ll be here I assured her.”

I slept fitfully that night wondering what the continuation of our “conversation” on the morrow might entail.

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