Chapter 1

I’ve always known I was a little different from most others. Even in my mid-teens (14 - 17), my friends were much older than me. By 14, I was already covered in body hair and could grow an effective beard and/or moustache.

But where I knew I was different was when the guys talked about sex. All my friends wanted to discuss was the female body’s mysteries. Who they’d had sex with and who they’d like to have sex with.

When they expressed their fantasies, it was about them and the girl of their dreams. I had those dreams as well, but mine were a bit different. My fantasies often had an extra element: a girl I fancied wanted me to join her and her friend, a friend with a dick.

I’m a tall guy with broad shoulders and long legs. During the years I’m reminiscing about, athletics had sculpted most of the fat off me. After that, I was all long, lean muscle and loose limbs. I didn’t consider myself good-looking but have been told I am by enough pretty girls to think it might be true.

Halfway through my second year at High School, my fantasies came shockingly to life! Just not in the way I’d thought.

My current crush, Cheryl, had suddenly started to invite me back to her place after class, ostensibly to study for the end-of-year exams. However, for some reason, her best friend Emma would always be there even though Emma and I had never exchanged more than two words.

One afternoon after track training, I knocked on Cheryl’s back door, shouted, “Hi,” and bounded up the stairs to her room. Cheryl’s parents both worked, so we had the place to ourselves for at least the next 2 hours.

I entered to find Emma sitting between Cheryl’s thighs. Cheryl stroked Emma’s hair and kissed her neck. A little taken aback, I nevertheless suffered an immediate rush of blood to my groin.

For an endless moment, all I could do was stand and watch. Then, slowly Cheryl peeled Emma’s blouse away till it fell away from her body. Emma sat tall and proud in her skirt and a lovely peach bra.

Cheryl wrapped her arms around Emma’s body, interlacing her fingers across Emma’s belly.

Watching me, she kissed the nape of Emma’s neck. Emma sighed and leant back into her. Cheryl slowly raised her hands and cupped Emma’s breasts, gently kneading them through the bra.

With her eyes firmly on me, Cheryl slipped her fingers inside Emma’s bra. She tweaked and pulled on Emma’s nipples, eliciting a sharply caught breath and a luxuriant sigh.

Pushing Emma forward, Cheryl undid Emma’s bra hooks. She brushed the straps off Emma’s shoulders, slowly revealing Emma’s firmly rounded, nubile young breasts. Emma leant back into Cheryl again and turned her head for a kiss. Cheryl gently stroked the sides and curves of Emma’s breasts as they kissed, occasionally returning to Emma’s nipples to either stroke or pinch them.

Emma began to softly moan, and their kissing became more fervent and passionate.

Reaching around Emma’s hips, Cheryl grabbed a piece of Emma’s skirt. Then, with her eyes again firmly locked on mine, she slowly pulled Emma’s skirt up by bunching the material in her hands.

I couldn’t not watch as more and more of Emma’s firm, toned thighs came slowly into view until I caught a glimpse of her white cotton panties. Confirming to all that Emma was a good sweet girl who would never do anything like this without the encouragement of her wanton friend.

Cheryl reached down below the hem of the skirt and placed her long painted nails on the inside of Emma’s thigh. I watched, mesmerised, as Cheryl slowly slid her fingers up Emma’s inner thigh till the tips of her nails brushed against Emma’s panties.

Applying a little more pressure, Cheryl ran her fingers across Emma’s mound and clitoris, eliciting a deep moan from Emma. Then, just as I thought I would explode there whilst standing in front of these two gorgeous girls, Cheryl’s bedroom door opened.

Not even glancing toward the door, Cheryl said, “You know Len, my boyfriend?”

I was standing there, the massive erection in my shorts obvious. It was also clear that I was lusting over his girlfriend.

Len is a high school senior, captain of the football team, and the most popular kid in school. He wasn’t quite as tall as me, but he was lithe, with toned, well-defined muscles. Len had olive skin, brown eyes, and honey-blonde hair that fell in waves to his shoulders.

All of the girls and, quite probably, many of the guys fancied him.

Rooted to the spot with embarrassment, I didn’t know where to look. Len walked across the room and jumped up on the bed. Then, spreading his legs, Len slid up behind Cheryl so that Emma was inside Cheryl’s thighs and Cheryl was inside his.

Len immediately started kissing Cheryl’s neck, reached around under Cheryl’s arms, and started fondling Cheryl’s breasts. Cheryl leant back into Len, sighing but kept running her nails and fingers over Emma’s pussy.

After a few moments of this, Cheryl’s eyes popped open, “Come closer,” she said to me, “And kneel between Emma’s thighs.”

In almost a trance, I took a couple of steps forward and slowly knelt between Emma’s luscious thighs. With a close-up view of Cheryl’s painted nails being dragged across Emma’s still-covered pussy, any thoughts I might have had about this being weird quickly disappeared.

Cheryl slowly slid two fingers inside the side elastic of Emma’s panties and slowly pulled them aside, revealing Emma’s closely shaven pussy. As the elastic dragged across Emma’s clit a low groan escaped her lips.

It was all I could do to not reach between my legs and stroke my hard-on.

Holding the panties to one side, Cheryl slid a finger across Emma’s clitoris and dipped it into Emma’s pussy. Emma’s moans were coming continuously, and I could barely refrain from moaning with her.

Just as I thought Emma and I would have to cum, Len jumped off the bed, marched across to me, and slapped me hard.

Stunned, I fell over, and Len immediately jumped on me, pinning my arms to my side and between his thighs. I was quite a big kid, but Len was two years older than me, and I was no match for him.

After he had slapped me a couple more times, I stopped resisting. Len waited until I looked up at him.

Curling his top lip, he said, “So you thought a worthless kid like you would really get to play with my girl and her friend?” And he slapped me again.

Not knowing what to do, I looked over to the girls.

Cheryl was watching intently with a look of lustful excitement on her face. But Emma was too busy luxuriating in Cheryl’s ministrations to even notice. Emma’s hips slowly thrust against Cheryl’s probing fingers, and little gasps escaped her.

Len hit me across the face again. “So, would you like the chance to play, you pathetic worm?” He said to me.

I looked across at Cheryl, who was smiling and nodding and grinding her fingers into Emma’s pussy, and said, “Yes”.

“Then you need to do as I say exactly!” Len growled at me. “I will let you up, and if you try to run or fight back, I will give you a proper flogging, do you understand?”

I nodded.

“Good! You will go with Cheryl, no questions asked, and do exactly as she tells you to, clear?”

Again, I nodded.

Len jumped up and reached down a hand to help me up. Then, pulling me up, Len punched me once, hard, in the gut. I doubled over, gasping for air.

“That is a warning, so you know what is coming to you if you don’t exactly do as Cheryl tells you to!”

Len motioned to Cheryl, and she slid out from behind Emma. Emma moaned a little in complaint, but Len put his hand behind Emma’s neck and grasped a handful of hair. Then, squeezing quite tightly, Len gave Emma a little shake.

“Don’t worry, my girl,” he said. “I will continue your lessons. Lesson number two, how to suck a cock!”

Cheryl signalled me to follow her. I walked out behind her, glancing back to see Len take his member out of his pants.

It was cut at least 7 inches long and much bigger than mine. I felt an unexpected jump in my cock as I glimpsed it. I was shocked at my reaction to the sight of Len’s cock, so I hurried to catch up with Cheryl.

Cheryl led me down the hall to her parent’s room. “Don’t worry”, she said. “My parents are away in Hawaii for the week.”

Guiding me into her parent’s bedroom, Cheryl told me to strip and indicated I should sit at her mother’s vanity.

“Len likes the ‘Gothic’ look on his girls”, she said.

I was confused, so I said nothing. Then, reluctantly taking my clothes off, I sat, stark naked, on the chair. Cheryl had positioned the chair so that I couldn’t see myself in any of the mirrors without turning my head.

Cheryl opened some of her mother’s drawers, taking out foundation, blush, mascara, eyeliner, eye shadow, and lipstick. Not sure what was happening, I sat quietly on the chair, watching her at work.

Having gotten everything ready, Cheryl poured some liquid foundation onto a sponge and reached toward my face. Shocked, I pulled away.

“If you don’t want me to call for Len, hold still”, she said. “You don’t want to interrupt his blow job because that will get ugly!”

Knowing I couldn’t hope to fight Len off and not really wanting to run anyway, I obeyed Cheryl’s command. Although my cock throbbed and jumped at the thrill of whatever might be going on here, I held still as Cheryl applied the foundation to my face.

Cheryl expertly spread the foundation evenly across my face giving an extra bit to my chin and jaw to hide my beard line. Once she was happy with my appearance, Cheryl put the sponge down and picked up some blush.

It was quite a dark red blush in keeping with the gothic theme. Cheryl applied it along my cheek line and then used a lesser amount under my jaw, blending it down my neck. This would help hide my facial hair and give my face more of an angular look.

Stepping back, Cheryl appraised her work. Then, happy with the result, she nodded and reached for the eye shadow. She chose black for the inner eyelid and dark purple for the outer lid, stretching it to just below the outside corner of my eye.

Pleased with how I looked, Cheryl quickly added eyeliner and mascara. Again she stepped back to assess my appearance.

As she expertly applied the lipstick, a little smile broke out on her face. Then, patting my hand, she said, “You make quite a pretty girl”.

Not knowing what to do or say, I sat there quietly.

“From now until I tell you you can, you’re not to look in the mirror”, she admonished me and walked over to an inbuilt wardrobe.

Opening the wardrobe revealed several wigs on polystyrene heads. Now I knew why Cheryl’s mum always looked so stylish and up-to-date. She had about 6 wigs she could mix and match.

Cheryl’s mum, Angela (Angie), was a relatively large woman, probably about a size 14 to 16, and was always dressed immaculately. Her figure was a buxom one. Not overly fat, just a big girl. Think Jayne Mansfield or her daughter Mariska Hargitay.

Choosing a medium-length jet-black wig, Cheryl walked back over to where I was sitting.

Placing the front of the wig on my forehead, she said, “Hold that there,” and pulled the wig back over my hair, hiding my closely cut naturally brown hair.

Cheryl teased and styled the wig using a brush and hair spray until it spiked up and stood out from my head. Satisfied with how I looked, Cheryl crossed to the walk-in-robe.

Sorting through her mother’s clothes, Cheryl picked out a short black dress for me and rummaging around the back of the robe, she found some black high heels.

Cheryl walked back across the room to me, “These are my father’s high heels,” she said with a mischievous grin. “They should fit. He thinks I don’t know about his cross-dressing, but I do!”

Opening a couple of more drawers, Cheryl produced a matching red bra and panty set. She told me to stand up and, in a daze, I complied.

My erection was standing achingly hard up against my abdomen. Moving quickly, Cheryl placed my arms into the bra and hooked it up behind me. Then, Cheryl smiled and spread her arms as if for me to come forward to be hugged. Eager to obey, I moved towards her. Dropping her arms, Cheryl thumped the heel of her palm hard into my balls. Gasping, I dropped to my knees, my erection quickly subsiding as the pain washed over me.

“Sorry”, she said. “But I needed to get rid of your erection. Now stand up and spread your legs.”

I struggled to my feet. Cheryl took my now flaccid cock in her hand. Then she stretched it back between my legs. After tucking my balls into their pouches, Cheryl produced a roll of gaffa tape and, working quickly, taped my cock and balls firmly into place.

Stepping back to admire her work, Cheryl handed me the matching panties, “Put these on,” she said.

I obeyed, scared she might whack me in my ‘boys’ again.

From yet another drawer, Cheryl produced a pair of black stay-up stockings. She showed me how to scrunch them up so I could easily slide them up my legs. Cheryl then helped me into the strappy, black high-heeled sandals.

“When you walk”, she said. “Small steps until you get used to walking in them.”

Motioning for me to sit back down, Cheryl brought out a bottle of nail polish. It was a red so dark it was almost black. One by one, she painted my nails, followed by my toenails.

“Almost done”, she said to me. “Once these are dry, I will put the dress on you, and we will go and see what Len and Emma are up to.”

Not sure if I should even ask, I said, “How come, if Len is your boyfriend, you allow him to play with others?”

Cheryl looked at me for a moment and said, “I am his girlfriend, but he is not my boyfriend, he is my Master, and it is not for me to tell him what to do.”

I was too afraid to ask any more questions.

Gently touching my nails to ensure they were dry, Cheryl carefully slipped her Mum’s short black dress over my head, not touching my makeup. Once it was on, she told me to stand up and move to the centre of the room. She walked around me a couple of times to ensure all was in place.

“One more thing,” she said. “My Dad has some breast forms here somewhere.”

Hunting through a few drawers on her father’s side of the room, Cheryl found a box with two C-cup-sized breast forms. Pulling the dress off my shoulders, Cheryl slipped the forms into my bra, cupping and moving them till she was happy with how they looked.

Cheryl readjusted the dress and said, “Alright, I’m going to turn you toward the mirror!”

Slowly turning around, I finally saw myself fully dressed as a girl, and the shock was too much! I slowly sank onto the chair. What was before me in the mirror was a beautiful Goth chick! She had a slim figure and nicely rounded breasts that her dress clung alluringly to!

Cheryl made me stand and slowly turned me around so I could catch a look at myself in the side mirrors. I saw that the 6-inch heels had made my bottom protrude and the muscles on my well-defined calves pop out.

My own mother wouldn’t recognise me, heck, I barely recognised myself!

“It’s a shame about the body hair”, Cheryl said. “But I don’t have time to fix that today, but you will be expected to keep all body hair shaved off. Now come with me.”

I followed Cheryl down the hall back to her bedroom in a daze.

Stepping inside, we found Len lying on his back, feet on the ground, his pants around only one ankle, with Emma kneeling between his legs. Emma was slowly running her tongue up and down the shaft of Len’s cock.

“That’s good, baby”, he groaned. “Now take the head in your mouth and swirl your tongue around it.”

Emma obeyed instantly before sucking Len’s member further into her mouth.

Immediately my cock tried to spring back to attention. However, the sudden pain from my balls in their tucked-up condition convinced me that wasn’t a good idea!

Hearing us enter, Len raised himself up on one elbow. Then, looking at me, he smiled and turned to Cheryl.

“Wow! Good job, miss!” He said. “Emma, jump up here on the bed. You,” Pointing at me. “Get on your knees where she is.”

I obeyed, not wanting to but feeling horny, confused, and completely unsure of myself.

My mind was racing as I sank to my knees in front of Len. I was terrified of what was to come, but I was thrilled and excited all at the same time. Len motioned me closer. Soon my head was only a few short inches from his cock. Len’s cock was rock hard, with the veins standing out thickly on the shaft and a dot of precum showing at the eye of the head.

Cheryl knelt beside me, also between Len’s knees. “Let me show you”, she said.

And with that, she wrapped her small delicate hand around Len’s turgid shaft. Then, bowing her head, Cheryl reached out with her tongue and tasted the pre-cum leaking from Len’s penis.

Again my cock throbbed, and the shooting pain convinced me to regain control quickly.

With a soft but firm grip, Cheryl swirled her tongue around the head of Len’s cock and stroked downward with the hand holding Len’s shaft. Cheryl slowly sucked more and more of Len’s cock into her willing mouth as her hand started to stroke more urgently.

I thought, “Wow, Len has some self-control, as I’m absolutely certain I would have cum already in his place!”

Reluctantly, Cheryl moved her head backward, allowing Len’s cock to slide out of her mouth. Then, still grasping the shaft, Cheryl pointed it toward me. “Your turn”, she said.

Unable to resist the desires welling up inside me, which were significantly heightened by the fact that I was enormously turned on and unable to express it with my usually extremely hard dick, I slowly moved towards Len’s dick.

Poking out my tongue as Cheryl had, I wonderingly tasted the clear fluid slowly leaking out of Len’s purple head. It tasted salty but with a pleasantly sweet aftertaste. Then, trying to mimic what I had seen Cheryl do, I swirled my tongue around the head of Len’s gorgeous cock.

It felt so natural somehow. Wanting more, I opened my lips and allowed the head of Len’s cock to slide into my mouth.

Len smiled at Cheryl. “I think we have a natural cocksucker here, girls”, he said.

Allowing my mouth to widen, I took more and more of Len’s hard throbbing dick into my mouth. Alternating between sucking hard and swirling my tongue around the head and shaft, I lost myself in the pure joy of giving pleasure to a man.

While still holding Len’s shaft, Cheryl moved forward and under Len and me. Reaching up with her mouth Cheryl started to lick and gently suck on Len’s balls. Cheryl ran her tongue along Len’s perineum and onto his little rosebud.

I have no idea how Len hadn’t shot his load by now, but I was glad he hadn’t, as I was lost in the sensations.

Hearing Len groan and feeling his beautiful cock jumping and throbbing in my mouth felt so exquisite!! Then, as I felt Len’s excitement rise, I was overcome with the need to feel him shoot his load into my willing mouth. And my mouth and tongue became more insistent, working feverishly to make Len orgasm.

Looking up to see if I could see how close Len was to cumming, I saw that he had positioned Emma over his mouth, facing Cheryl and me. Emma had lowered her pussy onto Len’s mouth, and Len was busily running his tongue over Emma’s clit and lapping at the entrance to her cunt.

Emma’s eyes were firmly fixed on the action happening between Len’s legs. A distant but focused look was on her face as her hips bucked and thrust at Len’s busily working tongue. Suddenly Emma tossed her head back, and a loud mewl burst from her mouth. Her thighs shuddered and squeezed together, and she bucked and trembled as an orgasm ripped through her.

As Emma was coming down, Len pushed her off and sat up. Then, Len slid back, making his cock slide out of my protesting mouth.

Cheryl climbed quickly back to her knees, and motioning me to join her, she placed her hands, palm up, on her thighs and lowered her eyes to the ground. Not sure what else to do, I mimicked her and waited to see what would happen next.

Watching avidly out of the corner of my eye, I saw Len reach into his sports bag. Taking out a strap-on dildo, Len tossed it to Cheryl, who, without seeming to even look, caught it deftly.

“I think we will take two virginities today”, he said, “Emma’s and hers”, indicating me.

I wanted to protest at Len calling me “her”, but I caught a glimpse of myself in the full-length window attached to the sliding door of Cheryl’s wardrobe, and the protest died in the back of my throat. But there was no denying what was looking back at me was a beautiful Goth girl kneeling obediently in front of an alpha male.

With the work Cheryl had done with the tape, and with two painful reminders of the pain associated with trying to achieve an erection whilst securely taped, there was no evidence I was anything other than what I presented in the mirror. I was a tall, thin, well-proportioned girl with full high breasts and a nice round, tight ass that her dress clung alluringly to.

Len stood up, pointing at Cheryl and Emma. “Strip,” he said. “Cheryl, strap that on and prepare her,” pointing at me.

Emma only had to drop her skirt as everything else had already disappeared when she had been teased and stroked by both Cheryl and Len.

Cheryl stood quickly and undid her blouse, revealing a nice lacy black bra. Then, peeling the blouse off and throwing it into the corner, Cheryl reached behind her and released the bra straps, and the bra quickly followed the blouse into the corner.

Cheryl had full, nicely mounded breasts. Not quite as big as the forms she had made me wear, but close. Her nipples were full and puffy, standing proudly out from her breasts.

Cheryl’s nimble fingers deftly undid the clasp to her skirt, and it dropped to the floor. Stepping out of it, Cheryl kicked into the corner to join everything else.

Standing tall and proud with her breasts jutting out and wearing nothing but a very skimpy G-string, Cheryl placed her hands on her hips. Then, with her thumbs tucked under the strings of the panties, she turned toward me and slowly peeled them off.

Despite my best wishes, my tightly tied cock jumped again at this fantastic sight.

By any standards, Cheryl was gorgeous. With long, firm legs that tapered to her hips, leaving a noticeable gap between her thighs just below her pussy. Her stomach was nicely rounded, as a woman should be, but there was only a hint of puppy fat.

Cheryl had trimmed all the hair off her pussy, and her vagina lips showed alluringly between her legs. Yet, despite everything, my cock twitched again, straining against the pain and restraint.

Picking the strap-on up, Cheryl did it up around her waist, then reached between her legs to do up the other tie-up strap, positioning the strap along her clit and between her pussy lips. The ‘cock’ part of the strap-on was relatively small compared to some I’d seen, only about 6 inches and not too fat.