Sissy Stepdad

Sissy Stepdad

Chapter IX

 

When I woke up the following morning, the first thing I did was make sure I had a couple of condoms in my pocket.  After last night’s disappointment, I made a vow to myself to never be without them.  Since I would never know when the girls would permit me to jack off, I needed to be prepared at all times.

 

As much as I=m sure you=d like me to continue relating my day-to-day activities in servitude to the eight cheerleaders, truth be told, I can=t remember much beyond that first week except a few major events.  Suffice it to say that the rest of the semester was pretty much a repeat of the first week, with a few changes from time to time.  I reported for punishment after school each day, which sometimes resulted in another whipping but often enough ended up being something else. 

 

They made me keep my used condoms, numbering each one and keeping a log describing the exact circumstances, in lurid detail, including when, where, how, and who was present to watch.  I was usually permitted to cum a couple of times a week, though several times I was forced to wait as long as three weeks.  Sometimes they made me jerk off six or seven times in just a few hours, after which my cock would be raw and sore for days. But it was the extended periods without relief that were the worst.  Waiting more than a week was nearly impossible for me, and twice I had to report that I=d had wet dreams the night before.  I wasn't permitted to bathe when that happened, but made to wear the dried cum on my legs all day long.  Then, during my afternoon punishment session, they=d have me scrape the flakes from my body and eat them.

 

Punishment slowly changed from physical pain to more of the humiliation I craved.  I still get aroused when I think of the time they made me participate in a practice session out on the empty football field one afternoon.  The story went out that I=d made the claim that cheerleading wasn't a true sport, and that anyone could do it.  The girls had put me on the spot and said that if I could make it through one practice, I=d get to have sex with any one of them that I wanted.  If I failed, though, I=d have to be their slave for a week.  With an audience of about 50 of my classmates watching, I failed, of course.  Not that I would have been able to succeed anyway, but it was predetermined exactly when I=d collapse.  The next step in my humiliation and subjugation was about to begin.  Now the girls could take it public, to some extent.

 

I spent the next five school days wearing a cheerleader=s uniform, complete with makeup, wig and an oversized brassiere holding the water balloons that substituted for a set of 44DD tits.  I was the butt of jokes from students and faculty alike, nearly every one about how cute I looked, or that wearing girls= clothes suited me.

 

After that week, it was no surprise when I was told I=d be going to the school=s Halloween party dressed up like a hooker.   It was Debbie=s idea, though several of the other girls wanted me to be a French maid and wait on them during the dance.  Instead, with Monique herself slathering makeup on my face, I was provided with a black leather mini-skirt and matching halter top, a pair of 6" spiked heel shoes, and fishnet stockings.  Because it was a school function, I couldn't go without underwear, so they put me in a men’s black string thing, with sort of a sack in front and a tiny strip of elastic that fit deeply in my ass crack.  It was the closest thing to a g-string for men I’d ever seen.  While I wasn't used for sex that night, I did have to walk mincingly from table to table, offering my body to everyone just like a real prostitute.  Everyone laughed; I=m sure most thought I was just trying to be funny, but I=m sure some knew otherwise.

 

Things got more intense after Halloween, too.  One time they made me order a male blow-up sex doll through the mail (thank God those things weren't available any other way back than), which I then had to take out on regular Adates.@  I would often find myself at the drive-in theater, in the back seat of one of the older cheerleaders= cars, dressed up like a girl, while my Adate@ would be sitting quietly in my only good suit.  While the girls up front would ostensibly be watching the movie, I=d be Anecking@ with my date, making appropriate girlish noises, eventually sucking Ahis@ cock.  The girls would even douse him in after shave, just to make it more Arealistic,@ they said.  They even made me call him, “Lover Boy,” and when I talked to him, I had to myself  “horny bitch.”  I had to make sweet talk on all our dates, too, nuzzling his ear and whispering how badly I needed his cock.  The girls, of course, made sure this was all recorded.  At one point, they even discussed having me take “him” to the prom as my date.

 

They actually gave me some time off during winter break, which was still called Christmas vacation back then.  Other than my thrice-weekly visits to the gym, I had no responsibilities unless one of them called, and that only happened twice.  I started enjoying my time at the gym - the workouts, that is, though the other part was pretty good too - and began taking fitness seriously.  I even started running on the days I wasn't in the gym, first a half mile on the school track, and eventually up two four or five miles at a stretch.  I could see the results in my body; no longer was I a skinny and bony, but there were muscles visible, too.  By the end of the semester, I was able to show Coach that I could do 50 consecutive pushups, and I even got an A in Physical Education for the first time in my life.  I couldn't swear to it, but I think my dick got longer, too.  Maybe that was just normal growth, though.  Or maybe it was the fact that, while I still sucked Bruno off before each workout, I wasn’t permitted my own relief until school resumed.

 

Things really changed for me when spring semester began.  Not only was I no longer taking P.E., but my afternoon punishment sessions went by the wayside.  Now, this was a good thing - bad thing for me.  The good thing was I no longer worried about getting caught with welts on my ass; the bad thing was the girls didn't worry about it, either.  The only thing that mattered was what things looked like on the outside.  Nobody would see that I was wearing lace panties, or stockings and a garter belt, or that my ass was bruised purple or had whip marks on it.  Counting me, there were only ten people in the world who knew that my toenails were constantly painted a bright pink, or that I usually had an overly large butt plug crammed up my ass.

 

There were other changes, too.  The nights that I didn't have to be at the gym, I was busy doing the girls= homework over at Carmen=s house.  It was just her and her mom, and mom worked evenings somewhere, so the girls and I would all go over there after school.  While they watched TV and chatted, I=d be sitting naked at the kitchen table doing their homework for them.  Once in a while, if there wasn't much homework, I=d spend the rest of the evening kneeling on the floor, licking toes, massaging feet or painting toenails, until it was time for everyone to go home. 

 

Gym nights were a little different.  We’d still all go to Carmen’s house where they’d relax while I did their homework, then at 8:00 we’d head over to the gym.  The girls would ride in their cars, and I would go on foot, running as my warm-up.  My jogging attire was nothing more than a pair of powder blue stain running shorts, but I quickly learned to carry a rubber or two in my clasped hand, just so I’d have one in case it was needed.

 

After stripping down and sucking Bruno off, he’d put me through my fitness routine.  It changed about once every two weeks just to keep it challenging, but I was beginning to enjoy the workouts.  I often voluntarily sucked him off a second time or gave him a tongue bath afterwards, just to show my appreciation.  The girls, of course, watched, made jokes, and photographed all of this.

 

After watching my workout, the girls would retire to the sauna.  I would be their cabana boy, fetching drinks, towels and whatever else they wanted.  They sometimes let me kneel on the floor and jerk off into a condom while focusing my eyes on their beautiful feet.  To this day, I still can’t look at a woman’s bare feet without my dick reacting.  After the sauna, they’d go into the showers and I’d go home.  I still wasn’t allowed to see any of them naked, and even when changing tampons, still wore the blindfold.

 

Whether it was a gym night or not, my chores weren’t finished.  Monday through Thursday, two of the girls would give me the soiled panties, bras and dirty socks they=d worn during the previous seven days.  Each night, I would dutifully hand-wash each dainty item then hang it in my room to dry.  Before school the following morning, I would rush to deliver the neatly folded undergarments to their owner=s home.  This meant two things for me.  First, on gym nights, I never got much more than two or three hours sleep.  Second, between doing their homework, laundry and whatever else they had me do, I never had time for my own schoolwork.  As a result, my grades plummeted.

 

Now, I was never going to be valedictorian or anything, but through my sophomore year I’d managed to pull mostly B’s, with a couple of A’s and a few C’s.  In fact, I’d never gotten anything lower than a C in my life, so my mid-semester progress report – showing a single C, two F’s and the rest D’s – came as quite a shock to my parents.  Of course, their first thought was that I was into drugs, and even after I assured them I wasn’t, they had me tested.  When that came up negative, They figured it must be emotional problems, so they sent me to a psychologist.

 

I’m sure if they’d known what was really going on, they would have found someone else, but Doctor Mary Franklin was a long-time friend of the family.  She was also very open-minded and had a bit of a dominant streak in her.  Not as much as the cheerleaders, but enough that she wasn’t averse to having me serve her, patient or not.

 

Our first meeting, she wanted to hypnotize me.  She said it was good therapy, but I wanted to be sure that whatever I said, wouldn’t be repeated to my parents.  I knew  I’d spill the beans under hypnosis; subconsciously, I wanted the whole world to know, and once my natural inhibitions against a public announcement were blocked, I wouldn’t be able to help myself.  It took three visits before I trusted her enough for that.  Each time, I let something else slip, and waited to see if my parents mentioned anything.  They never did, so on our fourth session, I told her to go ahead and do it.

 

Doctor Franklin found out everything, of course, including the fact that I secretly enjoyed the abuse.   She was completely understanding, and even gave me a few books to read, which really helped me understand myself better.  Each week, she’d expect an essay on whatever reading she’d assigned, and I’d mince around her office in my panties, dusting and polishing, while she read my innermost thoughts.

 

“You’ve never seen, let alone touched, a real vagina, have you?” she asked one day.

 

“Uh, no, Ma’am,” I responded.  Of course she knew the answer before she asked it; I’d confessed both under hypnosis and in my essays.

 

“Have your Mistress call me,” she instructed.  “If she agrees, that may change by next week.”

 

“Yes, Ma’am!” I acknowledged eagerly, my dick instantly straining against the front of the tiny purple panties I was wearing that day.

 

“Oh, don’t get yourself all excited,” she commented offhandedly.  “I have no intent to put that useless appendage of yours to use.”

 

“Yes, Ma’am,” I replied dejectedly.

 

“Your appointment is over.  Get dressed, and once the restroom is spotless, you may leave.”

 

“Yes, Ma’am,” I said, pulling my shirt on over my head.  My pants were always the first thing off and the last thing on, in accordance with Dominique’s instructions.  She was giving me a lot of little rules like that.  For instance, I was no longer allowed to pee in a urinal, and whenever I entered a bathroom or public restroom toilet stall, I had to immediately strip naked.  So, though I dressed to leave Doctor Franklin’s office, once I gathered up the cleaning supplies from the closet and entered the bathroom, I closed the door, took my clothes off, and began cleaning.  I wasn’t permitted to lock the door, and had to hope nobody would barge in without knocking.  Fortunately, that never happened during the time I was seeing Doctor Franklin.

 

When I gave Dominique the message from Doctor Franklin that evening, she just nodded and told me to continue massaging her feet.  The girls were all sitting on the couches watching some afternoon talk show; I was dressed in nothing but a frilly pink heart-shaped apron, in honor of Valentine’s Day.   The girls sat watching television, each enjoying their own large box of Godiva chocolates, while I absentmindedly rubbed Dominique’s feet.  I hoped there were no birthdays approaching; I had to go into debt to my sister again in order to afford the candy.  The forty I borrowed would cost me twenty in interest each week, plus I had to do her laundry until I paid it off. 

 

“Enough.  Go get your journal and read it to us,” Dominique commanded, shoving me away with the sole of her foot against my face. 

 

I mentioned earlier that I was required to keep my used condoms.  Each was individually numbered, and that number corresponded to a specific entry in my journal.  I was required to keep the journal with me at all times.  I scurried off on all fours (I wasn’t permitted to stand without permission) and retrieved the pink-covered notebook.

 

“Ma’am, where would you like me to start?” I asked, kneeling in the center of the living room floor.

 

“Why, from the beginning, silly boy.  After all, there aren’t that many, are there?”

 

“Yes, Ma’am.  I mean, no, Ma’am,” I blubbered, flustered.

 

“Which is it, yes or no?”

 

“Yes, Ma’am, from the beginning.  No Ma’am, there aren’t that many, Ma’am.”

 

“Well, now that we have that settled, begin,” she ordered, leaning back on the couch, smiling.  I could feel the eyes of all the girls on me as I started reading.  A total of 26 orgasms in four months, not counting the times I’d been forced to repeatedly jack off in the same condom until my dick was raw.  Quite a change from my former habit of masturbating at least twice a day.

 

As I recited the record of each condom in my, I would crawl to the girl who ordered me to cum that time and slather her bare feet with licks and kisses. Naturally, I was hoping that one of them would let me cum for their amusement; it had been eleven days, after all, since my last one.  That wasn’t to happen, though – as usual – and I was once again taken into the bathroom, blindfolded, and made to remove tampons with my mouth.  Two of the girls were on their period now, though I wasn’t sure who.  The last thing they made me do before sending me home in nothing but my skimpy blue satin trunks was to chew those used tampons until they were just a single bloody clump of cotton.  I carried it home in my mouth, my hands filled with bags of dirty underthings, finally disposing of the nasty-tasting object in the toilet after I arrived home.

 

A week later – a week without being permitted to orgasm, I might add – I had my next session with Doctor Franklin.  To my surprise, there was someone else in her office with her, a woman I estimated to be in her early forties.  She was pretty ordinary, actually rather dumpy when you get right down to it.  No makeup, a few pounds overweight, and in a frumpy cotton dress and clunky black shoes. 

 

“Why aren’t you dressed – or should I say undressed – properly for your session?” Doctor Franklin asked me sarcastically.  I started to stammer about the other person, but she interrupted me.  “Don’t you think I can see I have another patient in here?  In fact, don’t you think there might be a reason for both of you having appointments at the same time?”  I mumbled a “yes, Ma’am,” and quickly divested myself of my clothing, carefully stacking the folded garments by the door as was required, before kneeling at the doctor’s feet.

 

“Both you and Marilyn have problems that, coincidently, you can help each other with.  You see, you have no familiarity with the female anatomy except what you’ve seen in dirty magazines, and Marilyn thinks she’s frigid because her husband isn’t able to give her orgasms.  Marilyn is going to learn that it’s her husband, not her, and in return, you’ll get your first education in how to give oral sex to a woman.”

 

“Yes, Ma’am,” I replied, my eyes larger than they’d ever been.

 

Doctor Franklin led Ms. Marilyn (the name I was required to refer to her by) to the overstuffed chair in the corner – the same chair Doctor Franklin had reposed in, reading my essays, while I massaged her beautiful feet – and had her slip her white cotton panties off.  Speaking calmly to her other patient, Doctor Franklin set her back in the chair, then lifted her dress up and draped her legs over the arms of the chair, leaving them spread widely and exposing Ms. Marilyn completely to me.  It was the first time I’d ever seen a real, live vagina, but I was able to identify the various parts – labia majora, labia minora, clitoris – from the assignments Doctor Franklin had been giving me.

 

“Come take a close look, boy, but don’t touch,” Doctor Franklin ordered.  I crawled forward, resting my chin on the edge of the cushion and carefully inspecting the object of my desire.  My inspection was made all the more easier by the fact that Ms. Marilyn was shaved; a recent condition imposed by Doctor Franklin’s suggestion that doing so may cause her husband greater interest.   I knelt there for the next twenty minutes, just examining Ms. Marilyn’s vagina, allowing the vision to burn into my memory, before Doctor Franklin ordered me away.  After advising me that there would be no further patients today, she ordered me to lock the office door and get on with my cleaning while she continued her session with Ms. Marilyn.  I reported back to her  45 minutes later that the waiting room and restroom had both been cleaned.

 

“I understand your Mistresses only permit you to cum inside condoms?” Doctor Franklin said as I knelt there before her, Ms. Marilyn now completely dressed.

 

“Yes, Ma’am,” I replied shame-faced.

 

“Did you bring any with you?” she asked pointedly.

 

“No, Ma’am,”

 

“I see.  Marilyn, did you remember to do as I asked and bring one, just in case?”

 

“Yes, Doctor,” she answered, blushing beautifully as though her answer embarrassed her.

 

“Well, would you be willing to sell it to our boy here, so he can entertain us?”

 

“Um, Ma’am,” I interrupted, “I don’t have any money, Ma’am.”

 

“Oh, that’s okay,” Doctor Franklin said with a dismissive wave of her hand.  “I think six hours of housework for Marilyn would be an even trade, don’t you?”

 

“Yes, Ma’am,” I answered.

 

“So ask her!” she said impatiently.

 

“Ms. Marilyn, Ma’am?  May I please be allowed to perform six hours of housework of your choosing, in exchange for the condom you brought, Ma’am?”

 

“Well, I don’t know,” she said almost slyly.  “If I sold you the condom, what would you do with it?”

 

“Ma’am, I’d put it on my penis and jack off for you, if you wished me to.”

 

“But what would you do with it afterwards?”

 

“Ma’am, whatever you wished me to do, but I am required to add it to my used condom collection.

 

“I see,” she replied.  “Well, I suppose so,” she said, opening her purse and pulling out a single rubber.  It was one of those glow-in-the-dark ones, probably bought from a vending machine in a truck stop restroom.  That’s the only place I’d ever seen them.

 

Doctor Franklin and Ms. Marilyn allowed me to lay on my back and use one hand to play with my nipples while I jerked off for them.  This was a novelty – and quite enjoyable – for me, since I was normally required to jack off kneeling with my left hand on my head.  My nipples had always been very sensitive, and tweaking them during my orgasm always intensified the sensation.  Because it had been so long since I’d been permitted to cum, my orgasm was particularly strong, filling the condom to nearly the bursting point.

 

“What should we have him do with all that nasty boy juice, Marilyn?” Doctor Franklin asked, while I lay on my back, panting.

 

“Well, I certainly don’t want it on me,” she replied.  “I know we’d talked about having him rub it into my feet and then lick it off, but the thought of having semen touching me right now makes me shudder.”

 

“Hmm…okay, how about we just make him eat it.  Or better yet, pour it on his face and rub it in?  Didn’t you say your husband said cum is supposed to be good for the complexion?  We could find out, you know?”

 

“Great idea.  Okay, boy,” Miss Marilyn ordered, “Take the rubber off, empty it on your face and rub it in nice and good.”

 

“Yes, Ma’am,” I replied, carefully pulling the filled condom off my now-shrinking dick.  I wasn’t told to move, so I just remained on my back and held it over my face, allowing my own cum to drip out of the open end of the rubber.  Carefully rolling it up like a toothpaste tube to get every drop, I then began rubbing the semen into my skin, covering every part of my face.  My eyelids, nose, lips, and cheeks were all shiny from the wet fluid.  Once I’d rubbed it in completely, I was ordered to get dressed and go home, with instructions to not wash my face until after school the next day.