Adventures In To Bisexuality Pt. 02

Adventures into Bisexuality II: 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 University, and I would know 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.

To cover the fact that I was almost entirely hairless most of the time, I had joined the swim team, where it wasn't unusual for the male swimmers to be shaved down for competition.

When I arrived at Cheryl's room, I never knew what would be waiting for 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. Either 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 was 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 come 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). I offered to wear a condom, of course, 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. Often, they would then share a 'cum kiss', swapping my ejaculate back and forth between themselves.

About once 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, complete with a very short skirt with a side split almost to the top and her strapon already in position, taped to her inner thigh, with the head clearly in view below the hem of the skirt.

Those were the days I really 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, make me pull my shorts down, and kneel over her thighs before administering 'six of the best' with one of her dad's belts to my well-toned ass.

Cheryl would then have me sit in front of her mother's vanity and make me up into the vision of a gothic girl loveliness she had created for our first play session. She would then 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.

Once she was done making me up, Cheryl would place a collar and leash around my neck and lead me back to her bedroom with me walking dutifully two steps behind her. In there, we would always find Len and Emma in some flagrante delicto, usually involving 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 had come to enjoy this sensation so much I had to really grit my teeth and concentrate, so I didn't come '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 come 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 was caught. After one of the 4-way sessions, I was caught by Cheryl's dad Brad and then by her mum Angela (Angie).

Len had come in my ass. I had shot my load twice just from being fucked by Len without anyone, including me, touching my cock. And had been sent to get changed and go home whilst Len 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 of hers that I was wearing so I could take it off when I heard a very masculine "Ahem!" sound 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, 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 that I would simply die right 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 quite fine-boned with aquiline features.

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

I was thinking I could probably leap up on the bed and make a 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 had been 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, as well as a video of Cheryl leading me into his bedroom and transforming me into a girl, he had two still pictures of me, culled from the video, posing in the mirror, peering over my shoulder, admiring my shapely legs and ass and adjusting 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 to not 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 sporting what was a very large erection.

He had on a pair of expensive, well-tailored black slacks, 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. He, in fact, 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, 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, swirled it around the eye of Brad's cock, lapping up the precum already dotting there, and started to slide its length into my mouth.

Carefully pulling Brad's balls out of his underpants, I cupped them in the last three fingers of my left hand and circled my forefinger and thumb around the base of his dick. I grabbed the shaft of Brad's dick about halfway down firmly and was amazed to find that not only was there a gap between my right and left hand, but there was also still at least 3 inches of cock above my right 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 the fingers of my right hand off of Brad's shaft and, at the same time, 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 was able to control how much of his shaft I was taking.

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

My makeup, lipstick, and mascara were now smeared all around my face from the tears of my gagging and the drool from my wide-open mouth. 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 that I was wearing was pulled up above my hips, and her thong, which I was also wearing, was pulled to one side, 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 down to my 'breasts' and to my stiff dick. As Angie's eyes fastened onto my hard-on, she raised an eyebrow, and that traitorous member chose that moment to throb and jump like a new puppy greeting its owners.

"I assume this is Cheryl's latest girly 'boy toy'," Brad said, indicating me. "I've 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, a couple of weeks ago, I noticed they seemed to have moved again, so I set up a webcam to catch the culprit."

Angie sniffed, "What you mean is you wanted another video of us fucking to show your mates, again!"

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!"

My mouth fell open, and I gaped from Brad to Angie and back.

"Oh, do close your mouth, Janice! You're in no position to judge! Cheryl is not to find out, do you hear?"

Bewildered again, I nodded. I mean, what else could I do?

Angie walked around to me and took me by the hand. She pulled me to the middle of the room, where there was more space. Telling me to stand still, she walked around me, appraising me like I was a prize stud bull at a show. Brad just leaned against the wall with a smile on his face.

"Hmm," Angie said. "He has great legs and a fantastic toned, but quite round, butt." She gave one of my ass cheeks a squeeze, and I jumped. My dick, which had started to flag, jumped immediately to full attention, the traitorous bastard!

"He's very fit and has excellent body shape. Is already completely shaved down and has a nice cock, if a little smaller than I usually like, but it will probably be good for anal sex!"

Never before has 'the prize bull' analogy been more apt, I'd think! Unfortunately, at least one part of me was loving being treated this way as my dick was throbbing, and my sphincter was clenching as it throbbed. Precum was starting to leak from the eye of my penis.

Angie spoke to Brad, "You say she," indicating me, "was able to swallow all of you? I'd like to see that!"

She turned to me. "Strip my dress off and hang it in the closet. Get on your knees and show me how you managed to do what 'not even Angie can do'!"

Still unsure what was going on here, I thought it was best to do what I was told, so I took Angie's dress off, hung it in the closet, and knelt in front of Brad. Brad took his trousers off, folded them, and placed them on the dresser. He unbuttoned his shirt and pushed the shirttails behind his back, and, moving closer to me, put his hands on his hips and thrust his cock towards me.

A little more confidently than last time, I grabbed the shaft of Brad's large cock in the middle and proceeded to suck and salivate over the head, making it as wet and as slippery as I could. As I got more and more of his dick well lubed with my saliva, I allowed it to slide deeper into my mouth and slowly down my throat. As I got about three-quarters of his cock in my mouth Angie knelt beside me. She felt my throat and groaned. "I can feel his dick in your throat! There's a good little slut! Take it all for me!"

With only a slight hitch as it passed my gag reflex, I soon had Brad's dick all the way inside my oral cavity, and down my throat, with my nose pressed against his abdomen. Holding his hips, I pushed on them, so he slid back a little, and then I pulled him all the back way in. Brad soon got the hint and started to face fuck me. Starting slowly until he could sense I could take him all without difficulty, Brad began to throat fuck me in earnest. Tears were streaming down my face, wrecking what was left of my makeup, and drool was flowing profusely from my mouth. Brad grabbed my head with both hands and thrust into me faster and faster.

I heard a groan beside me. Turning my eyes to the right, I saw that Angie had hoisted her dress above her hips and had squatted really close to where Brad's dick was sliding in and out of my mouth and was fingering herself with two fingers dipped into her pussy. Her thumb was busy stroking her clitoris.

"Will he fit in your 'boy pussy'?" She moaned at me. I shrugged. "Let's find out, shall we?"

Angie pushed Brad off me and instructed me to get on my knees with my upper body over the bed. She pulled the thong I was wearing down and said to Brad, "Go slow. She hasn't taken someone as big as you before."

Brad squatted down. Angie took hold of his massive member and guided it to the entrance of my ass. Slowly she began to feed him into me. It hurt a lot at first. But I'd already been well fucked by both Cheryl and Len earlier, so it didn't take long for the walls of my 'boy pussy' to stretch enough to accommodate Brad's extra length and girth. Before too long, Brad was buried deep in my ass.

My treacherous cock was throbbing and jumping as he slid into my depths. Brad held still momentarily to let me get used to being this full. Then he gave a bit of an experimental push.

This pushed my erect dick against the side of the bed, sending exquisite feelings through my cock. I groaned. Brad took this as permission and pulled about a third of his length out of my ass before sliding it back in. He slowly slid further and further back, slipping more of his cock out every time.

He started to increase the vigour of his thrusts back into me until he was pulling everything but the very head of his turgid cock out of me before slamming back into me, his pelvis hitting my ass cheeks with a meaty thump.

I knew it wouldn't be long before I came. The extra girth and length sliding across my prostate was exquisitely delicious! But I desperately wanted Brad to cum in me at the same time as I exploded, so I was furiously doubling numbers in my head and using every trick I could think of to stop myself from coming.

Just as I thought I had to let go, Angie, who had been kneeling next to me watching the action and still playing with her pussy and clit, said, "Get him up on the bed! I need a dick inside me right now!"

Angie quickly stripped and dropped all her clothes to the floor. She scrambled up onto the bed. Lying on her back, Angie lifted her knees and spread her legs. Cupping one of her magnificent full DD breasts in one hand, Angie lewdly spread her pussy lips and said, "Right in here, baby, I need you to fuck me now!"

Brad pulled his entire length out of my ass, leaving me feeling empty, bereft and severely needing to be filled again so I could come. I expected him to send me home and climb up with Angie. Instead, he looked at me, indicated Angie, and said, "Well? What are you waiting for?"

I gaped at him! "You want me to make love to your wife?" I asked disbelievingly.

"No", Brad said. "I want you to fuck her just as hard and as well as you can!"

Still struggling to believe my ears, I hesitatingly climbed up on the bed and moved between Angie's voluptuous thighs. I slipped my hands under her shoulders with my forearms against her armpits. Resting most of my weight on my hands, I leant forward to give Angie a tentative kiss. Angie immediately grabbed me by the back of the head and dragged me down into a more passionate embrace. After a few minutes, we had to come up for air.

"You kiss very well," Angie moaned breathlessly.

I moved in to kiss her again, but, instead, Angie guided my head down to her breasts. Using all the skills I had learnt from her daughter and her daughter's friend Emma, I fervently tongue lashed Angie's beautiful full pink nipples. After a few moments of doing this, Angie groaned and guided me down to her pussy.