Chapter 2

Caught by Cheryl’s Parents

After my first adventure with Len, Cheryl, and Emma, our getting together became a semi-regular event. Cheryl would slip a note to me during class at school. I knew I’d need to head home straight after class, quickly shave down from head to toe, douche my anal cavity and present myself at her bedroom door.

I had joined the swim team to cover why I was almost entirely hairless most of the time. It wasn’t unusual for the male swimmers to shave down for competition.

When I arrived at Cheryl’s room, I never knew what awaited me. Sometimes Cheryl was simply horny and wanted me to tongue and finger her to an orgasm or two or three.

Sometimes I would find Len on her bed, with no sign of Cheryl. He’d be naked or have his dick out, so I could suck him off until he shot his load in my mouth. I became quite an accomplished cock sucker over these months.

If I were very fortunate, Emma would be over, and I’d find her and Cheryl 69ing each other, always with Emma on top, and I’d get to fuck Emma doggy style as Cheryl ate her pussy and licked my shaft and balls.

I was never to cum inside Emma’s pussy as she wasn’t on any birth control (her parents would freak out if they were to discover what a little slut their ‘good Christian’ daughter was). Of course, I offered to wear a condom, but she reckoned bareback felt better; well, it certainly did for me!

When I was ready to cum I’d tell the girls, and one of them would take my raging hard-on in their mouths and swallow all of my load. After that, they often shared a ‘cum kiss’, swapping my ejaculate back and forth between themselves.

About every 4 – 6 weeks, I’d arrive at Cheryl’s to find her standing just inside the door dressed in her School Mistress fetish uniform. The outfit consisted of a very short skirt with a side split almost to the top. In addition, she would have her strapon already taped to her inner thigh, with the head below the hem of the skirt.

Those were the days I looked forward to because I knew I was in for a real treat. In her best imitation of a School Ma’am’s severe manner, Cheryl would march me up to her parent’s bedroom. Then make me pull my shorts down and kneel over her thighs. Once in place, she would administer ‘six of the best with one of her dad’s belts to my well-toned ass.

Cheryl then sat me in front of her mother’s vanity. Then she made me up into the vision of a gothic girl loveliness she had created for our first play session. After she had completed my makeover, she would hand me her father’s high heels and breast forms, a matching bra and knicker set, one of her mother’s dresses, and a black wig.

After Cheryl was happy with how I looked, she would place a collar and leash around my neck and lead me back to her bedroom with me walking dutifully two steps behind her. We would always find Len and Emma in some flagrante delicto. It usually involved Len performing cunnilingus on Emma as she held the headboard and rode his face.

Cheryl would lead me to the edge of her bed, and I would kneel. Len would slide his hips towards me, and I would cup his shaft and balls in my hand and greedily swallow his rock-hard throbbing member.

Cheryl would lift the hem of her mother’s dress over my hips, slide the thong aside, administer some lube to my ‘boy pussy’, and fuck me with her strapon.

I enjoyed this sensation so much that I had to grit my teeth and concentrate so I didn’t cum ‘hands-free’ from her fucking. Len had shown his displeasure physically the one time I let that happen.

Once I had sucked Len to near orgasm, he would push Emma off his face, take Cheryl’s place at my well-stretched hole and proceed to fuck me like the dirty slut I had very quickly become. The best part of having Len in my ass was I could now cum as soon and/or as often as I wanted to or could!

Cheryl would mount Emma and fuck her with the strapon, and the whole room would be full of the delectable sounds of young people fucking.

The above, I guess, sets the scene for the story I want to tell you: The day I got caught by Cheryl’s dad Brad, and then later, by her mum Cheryl. So, reader, this is how it happened.

During our play session, Len had cumin my ass, and I had shot my load twice just from being fucked by Len. I’d cum just from being fucked in my ass by Len. No one had needed to touch my cock, including me. Having taken what he wanted from me, Len had been sent to get changed and go home whilst he finished servicing the girls.

I was standing on Angie’s side of Cheryl’s parent’s marital bed, trying to figure out how to undo the zip to the dress I was wearing. Whilst still trying to figure it out, I heard a very masculine “Ahem!” from behind me.

Assuming it was Len, I lifted the bottom of the dress, bent over so I could reach between my legs and slide the thong of Angie’s I was wearing aside. I mischievously said, “Can’t get enough of this delectable ‘man cunt’, huh? Well, help yourself, big boy!”

I looked between my legs and realised, with a shock, that it was Cheryl’s father!

“Oh, fuck!” I said.

I didn’t know what to do or say. I just wished the floor would open up and swallow me, or I would simply die there and then. If you could actually die of embarrassment, I would have had my wish already answered!

Brad walked around to the side of the bed I was standing on. Although Brad wasn’t quite as tall as me, he was very lithe, with well-toned forearms and biceps. Brad was also quite fine-boned with aquiline features.

In passing, I also noted that he seemed hairless across all of the parts of his body I could see. Brad kept coming closer and closer, and I kept backing up.

I thought that I could probably leap up on the bed and run for it, but where could I go? I had siblings at home, so I sure as hell couldn’t arrive home dressed like I was.

Shit! I hadn’t even taken Brad’s heels off yet!

Brad stopped when I was pressed back against Angie’s bedside table, and his crossed arms were pressing against my, well, his, really, breast forms.

“Hmm”, he said. “I noticed my shoes and breast forms were moved from where I knew I’d left them, so I resolved to set up a webcam and see what I could find.”

Brad pulled his phone from his pocket and showed it to me.

“And guess what I found?” he asked. “My slutty daughter bringing a boy up to my room! At first, I thought you two were going to fuck on our bed, and I wouldn’t have minded that she’s old enough to take a lover or two or three if she wishes! But what did I find? This!”

To my horror, Brad had a video of Cheryl leading me into his bedroom and transforming me into a girl. He also had two still pictures of me, culled from the video, posing in the mirror. I was peering over my shoulder, admiring my shapely legs and ass and trying to adjust my hard-on so it wasn’t so obvious.

“So”, Brad said. “What do you think I should do? By rights, I should probably show this to your parents and let them deal with you!”

I immediately started babbling and pleading for him not to do that. I was begging and looking down towards the floor, looking for a crack or something to hide in, when I suddenly noticed Brad sported a massive erection.

He had a pair of expensive, well-tailored black slacks on, which were much tented at his groin area. I had a ‘lightbulb’ moment and realised that Brad had no intention of dropping me in it. In fact, he found me attractive! So I lifted my eyes to meet his, smiled, and immediately dropped my eyes again.

I let my fingers trace around the head of his cock head that was pressing so salaciously against his trousers.

“Please, Sir! If you could find your way to overlook this,” I hesitated, “‘indiscretion’. I’m sure this girl would show you how grateful she was!”

Brad looked at me sternly, and I momentarily feared I had misread the situation. But then he unfolded his arms, took my elbows in his hands, and said, “Oh? And how would ‘this girl’ show me that?”

“Like this, Sir,” I said.

And went down on my knees, looked fetchingly up at him, and traced my fingers around his cock head again before unzipping his fly and taking his cock out.

I thought Len had a big dick, but Brad’s penis had to be at least an inch longer and thicker than Len’s. Undaunted, I opened my mouth, pushed out my tongue, and swirled it around the eye of Brad’s cock, lapping up the precum already dotting there. Then I began sliding its length into my mouth.

Carefully pulling Brad’s balls out, I cupped them in the last three fingers of my left hand and circled my forefinger and thumb around the base of his dick. Then, I grabbed the shaft of Brad’s dick about halfway down firmly. I was amazed to find there was still a gap between my right and left hand and still at least 3 inches of cock above my hand!

Still refusing to be daunted, I lowered my mouth onto the 3 inches of Brad’s dick above my right hand. Bobbing my head up and down, I pulled the skin of Brad’s shaft upward as I lowered my head and pulled it down as I took him deeper into my mouth.

Building up a rhythm, I slowly started lifting my right hand’s fingers off Brad’s shaft. At the same time, I let my circled thumb and forefinger slide down his shaft, so more and more of his length slid deeper into my mouth and down my willing throat.

Brad was moaning and groaning, holding my head in his hands and trying to force more of his cock down my throat. But with my two hands on his cock and abdomen, I could control how much of his shaft I took.

After a brief struggle as my gag reflex adjusted to the increased girth of Brad’s dick, I soon took almost all of his magnificent length down my throat. Finally, I felt a triumphant rush as I could take my right hand off his shaft and allow Brad to slide his whole length into my gaping mouth.

My makeup, lipstick, and mascara had smeared around my face. My tears, gagging, and the drool from my wide-open mouth had made my makeup run everywhere. I must have looked like a right slut! And I loved it!

“Fuck!” Brad moaned. “Not even Angie can swallow it all!”

Right then, a calm sultry voice asked, “What can’t Angie do?” Quickly followed by a much faster and more heated “What the fuck, Brad? Why is there some slut on her knees sucking you off in our bedroom? And why the fuck are you letting her?”

Brad merely groaned and continued to pump his cock in and out of my willing mouth. “It’s not what you think, babe. Hang on, look at what I found when I got home!”

Pulling out of my mouth, he bent over and grabbed me under my arms. I didn’t know what to do or where to look, so I turned away from Angie as I stood up.

“That’s one of my dresses!” Angie spluttered. “You bring some slut up here, dress her in one of my favourite dresses, and make her give you a blow job? What the living fuck, Brad?”

Brad just smiled. “I’m telling you it’s not what you think, Angie. Here, John, turn around!”

Mortified, I turned toward Cheryl’s mum. Her dress had slid above my hips, and Brad had pulled her thong aside, exposing my cock and balls.

Unfortunately, my dick had betrayed me, that ever-willing traitor, as I was rock hard. Angie looked from my wrecked makeup face to my breasts and stiff dick. As Angie’s eyes fastened onto my hard-on, she raised an eyebrow. That traitorous member chose that moment to throb and jump like a new puppy greeting its owners.

Brad Indicated me and said, “I assume this is Cheryl’s latest girly ‘boy toy’. I met him before when they were both studying for exams. I’m pretty sure his name is John but dressed like this, maybe we should call him Janice? And look! He already comes collared and leashed!”

Angie turned to her husband. “So, how did all of this happen, Brad?”

I could tell she was no longer angry, just curious.

Brad answered, “Remember, the other week, I asked if you had moved my heels and forms, and you said ‘no’?”

Angie nodded her head.

“Well, they seemed to have moved again a couple of weeks ago, so I set up a webcam to catch the culprit.”

Angie sniffed, “You mean you wanted another video of us fucking to show your mates!”

Brad just laughed. “Well, that too! But what I caught was this.” He showed the footage on his phone to Angie. “Seeing as I don’t work very far from here, I raced back to see if I could catch them in the act. What I caught was him trying to undress! He offered to ‘bribe’ his way out of trouble and was doing so when you walked in! Besides, you’re home early! What’s with that?”

Angie blushed! “Well, if you must know, I was horny and had just finished showing a client a home near here.”

Angie sells real estate.

“So I thought I’d drop home and see if Len was here, had finished making love to Cheryl and wanted to ‘double-down’ on the Adams women again by fucking me too! He is quite the goer, our Len is! She laughed wickedly. “As I’m sure you both know!”