Sissy Stepdad

Sissy Stepdad

Chapter VII

I was awakened the next morning to a pounding on my door.

"Wake up!  You're going to be late for school!" my mother yelled. 

Oh, shit!  I looked over at the clock, and saw that I only had twenty minutes until the bell.  Not enough time to eat, let alone get cleaned up. 

"I'm up!" I replied, jumping out of bed and throwing my robe on, then opening the door.  She didn't appear angry, so maybe she wasn't aware I was out so late.

"Hurry up, and I'll drop you off!" she said, turning to walk back into the kitchen.

I knew I reeked of my own sweat and the filth from the toilets I'd cleaned, but there was no time for even the quickest of showers.  I grabbed my deodorant from the top of my dresser - I'd moved all my hygiene items out of the bathroom in deference to my sister - and slapped some cologne on, in hopes that it would hide the noxious odors from others.  I didn't have any clean clothes, but my extra pair of jeans were quickly retrieved from the hamper.  I managed to find a shirt that wasn't too dirty or wrinkled, and threw it on just as Mom honked the car horn.  I rushed outside to find she had a brown bag breakfast waiting for me.  I gulped down the fried egg sandwich while she drove me to school, thankful that the smell of the eggs covered the stench from my own body from her.

"Thanks, Mom!" I said as she pulled up in front of the school to let me out.  It wasn't until then, when I saw Angela waiting with a scowl on her face, that I remembered.  I hadn't bought her any gifts, and I didn't have any money to buy her anything now.  I knew I was in trouble. 

"Guess what, slut?" she asked, a malevolent grin on her face.

"I know, Ma'am.  I don't get to cum today, right, Ma'am?"  I'm sure I sounded like I was about to cry.

"Bingo!  Okay, take my books anyway," she said, pointing to the pile on the sidewalk and walking off at a brisk pace.  I picked them up and followed.  We stopped at her locker, and I held her books while she opened it.  Taking the books from my hands, she looked at me thoughtfully.

"Maybe I will let you cum today, I just don't know," she said.  "Perhaps if you're especially obedient..."

"Oh, yes, Ma'am.  Whatever you'd like, Ma'am!" I replied, the eagerness evident in my voice.

"Okay, give me your undershirt, socks and shorts, right now!"

"Now, Ma'am? You want me to undress right here in the hallway, Ma'am?" I asked, shocked.

"No, you can go over into that doorway," she said, pointing to the janitorial closet, which was set back from the hallway by about two feet.  "Strip first, then put your shirt, shoes and pants back on - in that order.  If you underthings aren't on in my locker in two minutes, yesterday's punishment will seem like a day at the park!" 

"Yes, Ma'am," I replied forlornly as she looked down at her watch.

Thankfully, class had already started and the hallway was deserted.  I backed up to the inset door and quickly pulled my shirt over my head, simultaneously kicking off my shoes.  My jeans and undershorts came off next.  Twenty seconds later, I was re-dressed and my underclothes were in a pile on the floor.  I picked them up and returned to Angela's locker.  She motioned for me to put them inside, and when I did, she shut and locked the door.

"One last thing.  Kneel down and open your mouth," she commanded.  As I did so, she reached into her pocket and pulled out an object wrapped in a plastic sandwich bag.  "I was really hoping not to have to do this, but we didn't think you'd be here on time to help Carmen out, so she wanted you to have this," she said.  I looked up and saw her carefully holding a used tampon by her fingertips, even the string covered in menstrual blood.  She dropped it in my mouth, then presented her fingers to me.  I used my tongue to clean them off, barely successful in my attempt to keep from gagging as the nasty wad of cotton sat at the back of my throat.

"See you at lunch, slut!" she said over her shoulder as she sauntered off to her first class.

After running to the restroom and spitting the tampon into the toilet, I decided I'd better stop by the attendance office before going to class.  My first hour teacher was a bit of a hard-ass about tardiness, and he'd probably be sending me there anyway.  So I reported in as being late, got my tardy slip, and went to my civics class.  As had been the last few days, my mind wasn't into it, and the few questions I was asked resulted in stern looks from the teacher and giggles from the class.  The rest of the morning classes went the same.  Although I wasn't late for any others, between the soreness of my ass and preoccupation with my overall situation, I might as well not have been in school at all.

Lunchtime found me delivering my cafeteria tray to Angela, then making repeated trips to the snack bar to fetch soft drinks and refills while the eight girls talked about classes, cheerleading, boyfriends - in short, about everything except me.  It wasn't until Angela motioned me to clear their table of empty trays and cups that she even acknowledged my presence.

"There's a drug store two blocks down the street.  You know which one I mean?"

"Yes, Ma'am," I replied.  Of course I did, I walked by it every day.

"Go get me a pack of condoms," she said, dropping two dollar bills on the tray.  "Get as many as you can for that, and bring me back the change."

"Yes, Ma'am," I answered, wondering why she'd want me to buy her some condoms, and hoping the answer was that I was going to lose my virginity to her.  I figured it was a long shot, but what the hell, if you're going to fantasize, fantasize big.  Right?

So, after I dumped the trash and slid the trays through the dish window, I scurried off to the pharmacy.  Now, back in the early 1960's, rubbers weren't out on the self-serve counter like they are today.  Back then, you had to ask the Pharmacist for them.  I admit to being more than just a little self-conscious as I walked towards the back of the store.

"Can I help you?" the Druggist - a woman, which again was unusual for that era - asked.

"Um...yes, Ma'am...I need...um...."  I'm pretty sure my stammering was accompanied by a deep blush.

"Condoms?" she asked in a helpful voice.

"Yes, Ma'am," I answered softly.  "As many as I can get for two dollars, Ma'am, please."

"You and your friends planning on a gang-bang?" she asked as she turned to the proper display.   "Or do you just have a lot of girl friends?"

"Um...neither, Ma'am," I replied, thinking quickly.  "It's...like, a joke for someone."

"Oh, gonna blow them up and stick them in some girl's locker, then?  That happened to me, you know."  She turned back towards me, setting two three-packs down on the counter.

"Um, yes, Ma'am, something like that.

"Okay, well, I just want to warn you that we've had a lot of complaints about these particular rubbers.  If you really are going to use them for sex, well, I wouldn't, okay?  They have a tendency to break."

"Yes, Ma'am, thank you," I replied, stuffing the condoms, receipt and a few pennies change in my pocket.  I nearly ran out of the store, and believed I could feel her eyes following me, a grin on her face.

I got back to school just before the bell rang, but was unable to find Angela.  She must already be in class, I thought, so I went off to mine.  It was Algebra, the same class I'd messed up on the last exam in, and this time I was able to concentrate on my work, nearly forgetting the dull ache in my backside.

It wasn't until gym that I remembered the beating my ass had taken the day before.  Fortunately, I did remember that I wasn't wearing any underwear, managed to get out of my previous class a few minutes early - by claiming I had diarrhea, which was the only excuse I could think of - and by the time my classmates arrived to dress out, I was already in my gym clothes.  I'd completely forgotten about my bruised backside until I undressed for the shower.  Strangely enough, it didn't hurt at all, but much to the amusement of my classmates, my ass was covered with welts and deep purple bruises.  I could no longer just laugh it off, either, so just hung my head and said something about my old man getting drunk and laying into me.  In a few years, such a comment would have undoubtedly resulted in a visit by some social services agency, but back then, an ass-beating - and often enough any beating - was simply thought of as "parental discipline." 

I followed the same routine this particular afternoon as I had the previous few, lingering until I was the last one in the locker room, then after hiding my street clothes, knelt naked in front of the girl's locker room door awaiting my orders.  It was a cold, overcast day.  Not rainy, but damp, and the chill in the air was a sign of the coming winter.  Granted, winters on the central California coast aren't exactly harsh, but I still found myself shivering uncontrollably.  I waited and waited, unsure what I should do.  I knew the janitors would be coming soon, and I couldn't afford to get caught - no matter what my fantasies and dreams were.  I had just about decided to leave when I heard familiar female voices approaching.  Only they weren't coming from inside the locker room.

"Oh, were you waiting for us, slag?" Mary asked with a laugh.  "Debbie here got paid last night, and decided to treat us all to a nice, hot cup of cocoa over at Denny's after class.  We figured you wouldn't mind waiting, right?"

"No, Ma'am, I don't mind waiting, Ma'am," I replied dutifully, my shivering even more pronounced now, seeing the eight girls all bundled up in warm jackets, two holding styrofoam cups with steam coming out of them.

"Well, we decided we're not going to play tonight.  At least not here.  You can go home now, but be at Frankie's Gym at seven tonight.  You'll wear your gym shorts and tennis shoes, nothing else."

"Frankie's Gym, yes, Ma'am."

"Oh, one more thing," she said, almost as an afterthought.  "Except for your head - scalp, eyebrows and eyelashes - I don't want to see any hair on your body when you get there.  And bring your condoms."

"Yes, Ma'am," I replied softly, my voice shaking.

"Good.  See you then, hairless!"  The girls all laughed at the joke, but all I could do was, once again, turn bright red.

Because they'd waited so long to come back, I had less than two hours to comply with their wishes.  Retrieving my street clothes, I quickly pulled them on and ran the six blocks home.  Beth was already there, but was busy watching television.  She nodded absentmindedly when I asked if it was okay if I used the bathroom for a while.

I'd only recently started shaving, using a hand-me-down electric that my dad gave me.  I didn't have - or know how to use - a blade.  I'm not sure a blade would have been easier, but I suppose clipping the major hair - not that I had much, except a tuft above my dick - with the electric, and then shaving with a blade would have been less painful.  As it was, the electric not only tugged at the coarse, short hairs, but it took a lot longer than I expected.  It was already 6:30 by the time I was able to climb into the shower and rinse off.

Mom and dad had gone out somewhere, so I didn't have any problems getting out of the house wearing nearly nothing.  The girls hadn't told me I could wear street clothes and change at the gym, only what I was supposed to be wearing.  I decided not to take the chance, and with just ten minutes to spare, dashed out of the house into the cold, damp and now dark evening.  I ran as fast as I could; I had to, because Frankie's was over a mile away.  Like I said, I wasn't much of an athlete, but my light weight helped me in this respect.  Still, I was panting and out of breath by the time I arrived - just as the college clock tower bells began to toll.  I made it just in time, but the gym was closed!  I was trying to figure out what to do, when the door suddenly opened, and I was dragged inside by a strong hand on my arm.

The inside of the gym was dark, and I could barely see, but I could tell the person dragging me was a man. 

"Stay," he commanded, forcing me to my knees and leaving me there while he walked to the windows and pulled down the shades.  When all the windows were covered, he flicked on the overhead lights, bathing the entire gym - and my shivering body - in harsh brightness.  I looked up at him, a massive man with bulging muscles, as I trembled as much in fear as because of the cold.

"Stand.  Kick off the shoes, shorts down at your ankles, hands clasped behind your head," he commanded brusquely.  I did as I was told, standing there scared out of my wits while he slowly circled me.  I instinctively glanced downward, and saw that my dick was so shrunken it was barely visible.

"Squat.  Knees apart," he ordered next.  He pushed down on my shoulders, forcing me even lower.

"People call me Bruno," he said.  "You, however, will call me, ‘Big Daddy, Sir.'  Got that?"

"Yes, Sir," I replied.  My response was immediately followed by a kick to my shoulder, knocking me forward onto the floor.

"The girls said you were stupid.  Try it again.  What's my name to you?"

"Big Daddy, Sir."

"Good.  Now, get back up and into position."  I struggled to comply, my stomach doing flips now.

"They also said you were a scrawny fuck.  Are you?"

"Yes, Big Daddy, Sir.  I'm a scrawny fuck," I replied submissively.

"They said they're embarrassed to be seen with you, and want you bulked up some, so let me explain what's going to happen.  Tuesdays and Thursdays evenings after closing, and Sundays after you finish mowing lawns, you're going to come here for training.  Sometimes it will be just you and me, other times there will be other people here.  In return for me spending my time training you, you're going to do two things.  First, we start out the workout with you giving me a nice blow job.  Then, when we're all done, you play janitor and clean the gym.  Got it?"

"Yes, Big Daddy, Sir," I answered.  I knew I'd eventually be servicing men with my mouth - it was, after all, on my list - but like the other items, now that it was a reality, I wanted to run.

"Have you ever sucked a man off?" he asked.

"No, Big Daddy, Sir."

"Ever had a blow job yourself?"

"No, Big Daddy, Sir," I admitted softly, averting my eyes.

"Hmmm.  No base of experience to go by, so I guess I'll have to teach you."

"Yes, Big Daddy, Sir."

"You afraid?" he asked, with an almost concerned tone in his voice.  I knew it didn't matter whether I was scared out of my wits or not, I was going to end up with his cock in my mouth.

"Yes, Big Daddy, Sir," I replied, my voice trembling.

"Don't worry," he said, patting me on the head like I was a pet.  "It won't be so bad.  I won't even make you swallow my cum this time, since you're a virgin."

"Thank you, Big Daddy, Sir," I replied, actually somewhat relieved.

"Well, let's get started then, shall we?" he asked. I knew it wasn't a question, though.  "Just leave your shorts on the floor."

"Yes, Big Daddy, Sir," I acknowledged, obeying as he motioned for me to stand and follow him.

He led me into a small, dingy office furnished with a desk, office chair, and a ratty, well-work couch, pointing to a spot on the floor in front of the couch.  As I knelt there, I could see stains on the front edge of the seat - semen stains? I wondered.  He stood between the couch and my kneeling form, his legs on either side of mine.

"Keep your hands clasped behind your head, and pull my pants down," he instructed. 

"Yes, Big Daddy, Sir," I responded, lifting myself up off my heels so I was kneeling upright.  He was wearing sweat pants and the waist tie wasn't fastened, so all I had to do was grasp the hem with my teeth and gently tug, pulling them down first over one him and then switching sides to do the other, finally taking the very front in my mouth and pulling them down to his ankles.  I was surprised - but shouldn't have been - to discover a jock strap underneath the sweats.  He was, after all, a fitness trainer, and wouldn't exactly be wearing jeans and boxers for work.

I could smell a manly sort of cleanliness as my face moved close to his bare thighs, and was thankful that he'd apparently showered and changed into clean clothes.  I could only imagine what he'd smell like after a workout, but somehow knew I'd find out for myself soon enough.  The thought excited me, and I could feel myself growing erect.

I wasn't sure how to get the jock strap off, but decided to use the same technique as I had with the sweats.  First the left side and then the right, pulling the strap down over his hips.  To my dismay, however, he had to turn around so I could pull the back down.  His ass was covered with thick, curly hair - as I would later discover his whole body was - and I could smell the scent of his body even more strongly as I tugged, trying to hold my breath as much as possible.

With the top strap of his jock down over his hips, I returned to the front.  There was only one way to do this, I knew, and taking a deep breath, I reached up and grabbed the top of the cock pouch - I didn't know what else to call it - and pulling it as far out as I could, carefully jerked it down.  I wasn't able to avoid his cock, though, and it sprang up, bouncing off my cheek and striking me in the nose as soon as I had the garment down far enough.  Blushing, I ignored it as much as possible, pulled the jock strap down to his ankles, and released it.  I knelt there, my head down, face burning, not daring to look up.

"You're blushing.  How cute!" he said, causing my body to respond with an even deeper blush.  "And you seem to be liking this," he commented, tapping my now- hard cock with his foot.  I couldn't trust my voice, so I simply nodded my head shamefaced.

"Okay, just do whatever you think I might like," he told me in a calm voice.  "If I don't like something, or if I want you to do something in particular, I'll let you know."

I would have thought that after all this, he'd be hard, but he wasn't.  His flaccid cock, which was even now twice the size of mine, drooped limply against his left thigh.  I propped my hands on the couch on either side of his knees and carefully moved my face close.  Like I said earlier, I could smell soapy cleanliness, but still there was a bit of manly scent about him.  I rubbed my cheek against the inside of his thighs, slowly moving closer and closer, until my eyes were mere inches from his cock.  I studied it carefully, noting its symmetrical head, the tiny slit staring at me.  I half-imagined it to be a snake, ready to strike.  I noted the blood vessels, like little tubes, or maybe worms under the skin, slithering to and fro.  The follicles covering his balls - his entire pubic region - with a thick coating of curly hair.  I nuzzled those balls, too, feeling their fur coating scratch my face, inhaling their not unpleasant odor.  I moved my head slightly, allowing my lips to contact his now-hardening shaft.  I kissed the underside gently, moving from base to tip, my lips moving like those of a goldfish, softly opening and closing as I lightly brushed them against him.  I ran my tongue around the contour of his dickhead, licking ever so lightly under the ridge of his circumcision.  I took it into my mouth, grasping him with my lips and feeling his penis pulsate ever so slightly.  I began to suck gently, just the head in my mouth, my lips locked at the top of his shaft, and was rewarded with a low moan and the feeling of his hands on the back of my head.

At his urging, I slowly began taking more and more into my mouth, the feel of his throbbing cock causing my own to react.  He slowly forced my head forward until my nose was mashed into his belly, then pulled back slightly as my gag reflex began to activate.

"Relax.  Breathe through your nose," he told me calmly, then applied more pressure to my head, forcing me to engulf him fully once more.  Three times he released me, then forced me back down, until I was able to overcome my fear of choking.  Slowly, he began fucking my face - that's the only way I can describe it - his hands forcing my head forward and back, impaling my throat and then pulling nearly completely out of my mouth.  He quickened his pace, not forcing me as far forward now, concentrating on the top third of his cock, making me suck forcefully on the head.

"I'm going to cum!," he announced, releasing my head.  "You don't have to swallow."

I responded by leaning as far forward as I could, taking him as deeply into my throat as possible and massaging his cock with my tongue.  I sucked harder than I ever had before, feeling his penis start to pulsate even more, until a few seconds later, I was rewarded with a forceful blast of semen hitting the back of my throat.  I coughed in surprise, but kept my lips sealed around his member, swallowing as fast as I could while he spurted into me.  As the spurts slowed down and became less forceful, I became aware of the fact that I, too, had managed an orgasm - without even touching myself.  I opened my mouth began gulping down fresh air, both of us panting in the otherwise quiet room.

"That was phenomenal," he said.  "You're sure you've never sucked cock before?"

"No, Big Daddy, Sir," I gasped, still trying to catch my breath and wiping a bit of cum from my cheek.

"Damn.  I've never met anyone who was able to deep throat the first time!"

"Was that what I was doing, Sir?  I mean, I've heard of that, but never knew what it meant."

"Yes, that's what you were doing," he said, grinning down at me.  "It seems I wasn't the only one who had a good time, either," pointing at the puddle of semen on the floor.  "Don't you think you should clean that up?"

I started to bend over, thinking that he expected me to lick my own cum off the floor, but he stopped me.

"No, I meant with a towel or something," he said.  "But if you want to use your tongue, that's okay too.  The girls did say you were submissive."

"Big Daddy, Sir, I really would prefer to use a towel, Sir, if you don't mind."  He reached behind him and took one that was draped over the back of the couch, tossing it down to me.  I quickly wiped up my mess, then knelt there awaiting further instructions while he got dressed.

"Okay, let's go get you started," he said, motioning me to follow him out to the exercise floor.

I have to admit that I was pathetic that first night.  He took me around to each piece of equipment, showed me how to use it, and then we found out how much my maximum weight on each exercise would be.  Bruno said he'd never seen anyone as out of shape as me, except for fatties.  I was only able to curl 10 pounds, and bench press 30.  He had me do pushups - perfect pushups, not the kind I'd been able to get away with in class - and my arms collapsed after four.  The same with sit-ups, though I managed 12 of those.  In the end, he set me up with a program of light weights with high reps to start with.  Making sure I understood each of the exercises I was supposed to do, he then set me to work.

I had just finished cleaning the toilets and was mopping the floor in the women's locker room when the girls showed up.

"No, this won't do at all," sixteen year old Angela said.  "You're improperly dressed to be a cleaning maid."  I stopped and began to remove my shorts, figuring they wanted me naked.

"No, no, no, silly boy," she said.  "You need to put THIS on!"  She reached into an unlocked locker and pulled out a grey cotton dress.  "Maybe if you're good enough, you'll eventually promote to something nicer, like a French maid's costume!"  They all laughed while I slipped the frumpy garment over my head, then continued to make crude and humiliating comments about me while I finished my work.

"Did you bring your condoms, boy?" Mary asked when I was finally done.

"Yes, Ma'am," I replied.

"Good.  Strip, go get one, then bring it back here," she ordered.

"Yes, Ma'am."  My mind was rushing as I thought of all the things that could happen here.  Maybe I was going to get to fuck one of them...or rather, one of them was going to fuck me!  Staying on all fours, I crawled as fast as I could back to Bruno's office, where I'd dropped them.  Ripping the box open, I grabbed a single rubber and rushed back to the women's room.

"Put it on," Mary's twin, Susan, ordered. 

"Yes, Ma'am!" I answered excitedly, ripping the package open and carefully slipping the sheath over my erection.  I knelt there, anticipating, my eyes moving from one cheerleader to the next.

"You may now show us how you pleasure yourself," she said.

"Ma'am?" I said, confused.

"None of us have ever seen a boy jack off, so do it!" she explained.

"Yes, Ma'am," I replied, dejection apparent in my voice.

"Oh, did you think one of us was going to let you stick that nasty thing in her?" Angela laughed.  "Sorry, little boy.  We only fuck men."

Dejected, I reached down and began masturbating for them, keeping my legs spread as they demanded so everything was visible.  During my humiliation, they ordered me to tweak my nipples, change hands, even suck on my finger and stick it up my ass.  It was in that position - my right hand wrapped around my cock, my left index finger up my ass - I was in when my balls finally emptied into the condom.

"Not much there," Dominique commented.  "Have you been disobeying us?" she asked, her hand grasping my chin, forcing my head to look up into her eyes.

"Ma'am...no, Ma'am, but when Big Daddy, Sir, made me suck him off, Ma'am, when he came, so did I, Ma'am," I stammered.

"‘Big Daddy, Sir?' Where did that come from?"

"Ma'am...Bruno, he said I was to call him ‘Big Daddy, Sir,' Ma'am."  The girls all laughed at that one.

"Okay, I guess a slut like you couldn't help it.  Swallowing cum must be something that turns you on, right?"

"Yes, Ma'am," I replied.  I knew better than to say otherwise, and wasn't all that sure it wasn't a fact anyway.

"Okay, one more thing and you're done for the night.  Carmen needs her tampon changed again."

"Yes, Ma'am," I answered, holding my head still so she could put the blindfold on.  I waited while Carmen got in position over me, then feeling her thighs against my face, I stuck my tongue out and moved it around until I found the string.  Clamping my teeth down, I tugged gently until it fell out, landing directly on my lips.  I opened my mouth and let it fall inside.

"Chew, chew, chew!" I heard Dominique's voice say.  "Yummy!"  I did as she ordered, feeling the sogginess squish between my molars as I chewed, swallowing the vaginal blood that was squeezed out of it.

"Keep the tampon in your mouth and the condom on your dick until you get home.  Once you're there, you can dispose of the tampon.  Take the condom off without losing the contents, tie it closed, and bring it to school tomorrow.  Understand?"

I nodded, afraid to open my mouth for fear the tampon would fall out.

"Susan is in charge of you tomorrow," was the last thing I was told before the girls walked out, leaving me alone in the darkened gym.