The Derailment of Tom Ch. 01

Lucas and I met half way through high school, and over a period of about 6 months, realised that we were going to become pretty good friends. We liked the same sports and the same computer games, and always found time to hang out together at the shops, the movies, or on trips to the beach when we could fit it in. Lucas also had a lot more freedom than me to have people round to his house, so it was never a problem to crash there. Perhaps the only thing I didn't like about him was that he was a bit ahead of me in the dating game - often picking up at parties, and by the time we left school, having a steady girlfriend called Alison. He was taller than me, more sporty, and way more relaxed and confident in social settings. Meantime I was still trying to get up the courage to approach girls.

This changed for me when I went to University, and Lucas introduced me to Debbie - a friend he'd met during the holidays who I later found out had a bit of a track record of going after what she wanted. We met at a party, and I quickly found myself pulled into one of the bedrooms for some very heavy kissing and fooling around. Debbie was in touch the very next day, and soon I had my first girlfriend.

I guess it's typical of the age, but at 18 we were pretty split in our attention between trying to get laid, and trying to maximise our time hanging out in the city, eating pizza, and gaming, so despite both Lucas and me having a partner, there was still plenty of 'guy time' to be had, and it was a rich environment to trade stories. It turned out both girls were adventurous. Lucas would report that Alison had 'christened' the gear stick in his new car, or tell me about them trying anal for the first time. Meantime Debbie was interested in finding out my secrets, alongside a very happy routine of frequent sex anywhere we could sneak it in.

And I ended up being happy to share my secrets. I enjoyed the thrill of a sexual partner who was not only intrigued, but seemed genuinely excited by some of my dirtier thoughts. We played with food, and had sex in public spaces. I went down on her in the corridor of a nightclub. She sucked me off while we were sharing a bedroom with other party guests. But the thing that seemed to excite her the most was when I confessed a particular fetish I'd kept hidden from everyone - the thrill of sneaking on a pair of women's panties. This came out in a situation where I couldn't really resist - naked in my bed while my parents were out, Debbie sitting behind me and gently stroking my cock, while murmuring ideas and questions in my ear.

"Tell me something else you've never shared, Tom," she purred, and as my dick throbbed and strained, I let the secret out.

"I want to wear panties," I whispered.

There was the slightest hitch in her rhythmic stroking, and a soft chuckling in my ear.

"Oh my god, a little panty boy!" she giggled, not letting up on masturbating me. "Should we try it right now?"

I found it hard to say yes, embarrassed by how suddenly I'd shared it after many years of secrecy. But Debbie wasn't bothered. I felt her untangle herself from where we were sitting, and she quickly rummaged around on the floor to produce the pair she'd been wearing that afternoon. I recognised them; a light blue satin brazilian style that really showcased her bum.

"Do you like these ones, Tommy?" she said with a grin. "Come on, stand up."

I did, feeling awkward at how my cock stuck out, rock hard.

Debbie knelt down and coaxed one foot then the other into the panties, drawing them gently up to my crotch. The material felt heavenly, and she soon had then wedged tightly up against my ass, with the front pulled up over my balls. There was no way my cock was going to fit into them in its current state!

"Mmm, that looks very cute, sweetie!" she said, and she remained kneeling in front of me, one hand cupping my balls through the silky material, and the other gently caressing one cheek as she took the head of my cock in her mouth.

It was way too much excitement for me, and in seconds I was shooting cum into her mouth, which she then allowed to drool out onto her large boobs. I think I nearly passed out from cumming so hard, and the glorious sight of her enjoying my load.

After that, Debbie made a regular habit of working dress ups into our sex life. She would encourage me to wear her panties, especially to events where only the two of us would know what was under my jeans. I'd find her touching my ass or whispering naughty comments in my ear when family or friends were dangerously close, and it always led to intense fucking as soon as we got the chance. Often I'd leave her panties on and just take my cock out the top, and occasionally, she'd wriggle out of her bra and push the straps around my arms, exciting both of us even more.

The relationship wasn't perfect - of course - but I'd found a real nirvana when it came to a sex life.

-----

The relationship between the four of us - Debbie and me, Lucas and Alison - was a little strange. Alison was a bit distant, and I'm not sure she'd have approved just how much I knew about her sex life, even though Lucas assured me she liked him talking about it. Meantime Lucas and Debbie were good friends, so I worried a little about what might be being shared in the other direction. But he never said anything to indicate Debbie had told him my particular secret, and so life went on in pretty enjoyable fashion.

Then out of nowhere one night, Lucas called wanting to talk. It turned out Alison's family was moving overseas, and they were thinking about breaking up. He seemed unusually down about it - normally he got bored of relationships pretty fast, and I'd have thought this was a perfect opportunity for him to start hunting again. But as we talked about it, I realised he'd been genuinely hoping the relationship would last. It was a side of him I'd never really seen before. In the end, they decided to take a break, without being all that clear about what it meant for the long-term. I was a bit concerned they didn't seem to have a clear plan at all, but as the weeks ticked down, they still seemed pretty happy together, and were making plans for how to schedule their video calls and holidays.

At the end of semester, Alison was on a plane, and it meant the summer was going to be a bit lopsided unless Lucas broke things off and found another girlfriend. But he seemed OK with things, and the situation led to the three of us hanging out a lot more often - me, Debbie and Lucas. Debbie liked him, and was always happy to fit him into our plans - which to be honest didn't amount to a lot more than going to cafes and movies, crashing on the couch with some takeaway, and sneaking in as much action as possible whenever we could - often while Lucas was on the phone to Alison. At the time, we were all still living with our parents, which was a bit frustrating - but Lucas' folks were constantly away traveling, so his house became the default spot. It was also a big rambling property with a pool and tennis court, and me and Debbie could have a spare bedroom to ourselves.

One night when Debbie was out with some friends, Lucas and I were watching TV and a bit bored.

"Hey, are you thinking about whether to keep going with Ally" I asked, wondering if the current lull was going to continue much longer.

"Mmm, dunno man," he said, "I miss her a lot. But like, it's not the best not having her here."

It was the first we'd really talked about it, so I was pretty curious. "Like... was the relationship that much better than other chicks?" I asked. "She was great and that... but I didn't know her that well, I guess."

"Oh it was OK," he said, "like... it was kind of the sex more than anything."

"Oh... uh huh," I said, not quite sure what to say to that, but feeling a tingling in my nuts when I thought about some of the things he'd shared along the way. "So like, do you - are you OK not getting action now?"

"Well I kind of do... she's still up for stuff on the video," he said.

"Right, but it's not exactly..." I trailed off and took a slug of my beer, not sure how to put it.

"It gets pretty wild still," he said. He looked over at me like he was weighing something up. "Can I show you something?"

"Like what kind of thing...?" I said cautiously.

"Stuff Ally and me recorded. It's OK to see it - she... well, she told me I should share it with you guys. I think it turns her on."

"Oh..." I tried to be noncommittal, but my cock was suddenly rock hard and I had to shift a bit in the seat to make sure it wasn't too obvious. "OK, then, yeah.... I guess".

Lucas fetched his laptop from the study, and set it up on the coffee table, before opening some increasingly wild videos that he had saved. I felt pretty awkward seeing them, but at the same time, I had to admit a huge part of me was very turned on by it. In the first one, there was Alison, looking a bit awkward as she pulled off her top, displaying a very admirable pair of breasts that I'd only ever seen in a bikini before. It looked like Lucas' bedroom here in his house though. "This is one we did before she left," he said. And sure enough there was Lucas, completely naked, moving from the camera to the bed. With a bit of fumbling, he proceeded to remove her pants, apply some lubricant to what looked like a decent sized cock, and begin taking Alison doggy-style. Although it was on-screen, it felt like I was sitting in a room watching them screwing right in front of me, which wasn't something I'd experienced in my life. I could feel an erection straining in my pants, but the whole thing was sort of bloodless compared to how the actors in porn went about it. There was grunting and the rhythmic slap of Lucas' crotch against Alison's ass, and her gasping and her boobs swinging beneath her torso, which all went on for a while before he tensed up hard, his glutes thrusting firmly, and jerked fiercely as he orgasmed inside her. I wasn't sure if Alison had come or not.

"She really likes it from behind," he said.

I sipped my beer and couldn't think of anything intelligent to say to that. I wondered what I would look like in the same position; certainly I didn't have the impressive muscles to carry it off the way he did. Watching his firm ass bunching and humping her made me feel a little ashamed about my comparatively slim body.

In the next video, he'd filmed her going down on him, getting some really close footage of Ally in a bra and panties, kneeling on his floor. Lucas' cock was definitely pretty big, because despite what looked like some very good skills, Ally had to work hard to take the whole thing in her mouth. She licked and sucked furiously at him, while also squeezing his balls, and the two of them made plenty of noise. Before too long, Lucas groaned and shot a huge load of cum all over her face, then held the camera steady as she carefully cleaned it off with a finger, sucking the cum into her mouth, and swallowing.

When that ended, he looked at me again. "Anyway... like... she wanted me to show them to you. Is it OK if I tell her?"

"Yeah..." I said, "but she'll tell Debbie as well right? I think we should tell her I've seen this or she might get pissed off."

"Nah that's fine man," he said, "just let Debbie know when you see her tonight. It's all OK. And to be honest man, I'd be surprised if Ally didn't share them with Deb already."

It was a bit weird going back to watching TV after that, and remaining casual when Debbie got home. She was a bit drunk anyway and wanted to go to bed, so we called it a night. Debbie was quickly asleep though, so I lay there for a while thinking about the video. Especially the second one. I imagined Ally was sucking me off instead of Debbie, and kept picturing how thick Lucas' cock was, and the thick ropes of cum exploding across her face. Eventually I had to sneak off to the bathroom and give myself a furious handjob before I could get to sleep.

The next morning while we were lying in bed still, I told Debbie what had happened. "Why do you reckon he did that," I asked, "do you think it's a bit weird?"

"Like you're not into anything weird!" she laughed, and I felt myself blushing a bit. "I suppose it's their thing," she said, "I reckon they like being exposed. Remember that time we went round and caught them fucking in the living room? I'm sure that wasn't an accident really."

I shrugged, unconvinced. But I remembered that incident pretty well. We'd walked in one afternoon and discovered them almost completely nude on the couch, Alison sitting on Lucas' lap and clearly frozen with his cock buried deep inside her. Ally had squealed in surprise and scrabbled for clothes to cover herself, but Lucas had an embarrassed but wide grin on his face as we backed out of the room. I thought I'd caught a fleeting eyeful of his cock coming out of her as she reached for the clothes, and in my memory, it was wet with Allison's juices - but I wasn't sure if that was reality or just a fantasy version of the incident.

"Hey!" Debbie said, whacking my arm. "What are you thinking about?!"

Shit. I'd obviously zoned right out thinking about the couch incident, and been caught red-handed.

"Sorry!" I laughed. "Yeah, that was some afternoon." (The 'some' part was that we'd scuttled off to the spare bedroom, before hearing Lucas and Ally starting up again in his room, which got Debbie right in the mood. I'd ended up fucking her against the adjoining wall while listening to Ally getting railed about 2 meters away, and Debbie had cum really hard).

"So tell me all about the videos, anyway," she said. I gave her a rundown, and while I was describing the first one, I felt her hand slide down and hold my cock, which was completely stiff.

"Go on, tell me the other one," she breathed softly, gently stroking my cock, "tell me in detail."

"Well, so... she was in her underwear," I said, starting to breathe a bit more rapidly.

"Wearing what?"

"Like... bra... a white bra and white panties"

"Did you like them?"

"Mm hmm," I nodded.

"She probably had a super wet pussy," said Debbie, who sounded pretty excited by the idea. "Was his cock really big? She says he has a big cock."

"Yeah," I said, "it's pretty big. She was struggling to get her mouth around it."

"Oooh. A nice big cock."

She paused and let go of me - frustratingly, because I was started to get pretty worked up. Debbie got off the bed, rummaged on the floor, and came back holding some of her own underwear.

"Put these on," she said, unexpectedly.

"Huh?"

"Hurry up!" she hissed, a tone which I knew not to mess with. I pulled off my boxer shorts and pulled on her panties instead - a light blue pair that came with a matching crop-top style bra. She helped me wriggle into the bra next, smoothing the front over my chest and very hard nipples. I squirmed a bit, feeling my cock already leaking precum into her panties.

"Right... now keep going," she said, her hand moving down and caressing me through the panties again.

"OK... um... so Lucas has his cock out and he's filming this, and she's like, she has one hand on his cock and one on his nuts as well."

"Show me how it looked?"

"Um... so like... I went to stand up and pull my cock out, before realising what she meant. Her eyes locked on mine and she had an evil grin.

"Go on, Ally", she said. "Get on your knees."

My heart thumping, I knelt down beside the bed, and Debbie spread her legs in front of me, revealing that the front of her panties was already sopping wet.

"Now tell me in the first person, you slut," she said.

I swallowed hard, trying to breathe.

"Uhm... so she... I mean, me. I was kneeling in front of him," I said, and she nodded and snaked her right hand around my head, pulling it gently in between her thighs. I could smell her juices strongly.

"Lick my cock, Ally," she said, pulling me forward. My tongue came out and made contact with her pussy through the wet material, and I lapped at her.

"Oh yes, you slutty fucking bitch," Debbie said, pulling the material aside to give me direct access. I rammed my tongue deep into her and began sucking and licking at her as hard as I could, panting each time she released the pressure on my head.

"Keep talking, slut," she said, looking down at me. "Tell me in detail."

"Oh god," I panted, "I was kneeling there and kept sucking and licking him - his big cock."

"Taking it in your mouth?"

"Yes, sucking it and taking it in my mouth."

"Yeah you sucked it, you little whore... you sucked him off didn't you?" I couldn't answer immediately, because she rammed my face into her crotch again and ground her hips, smearing my entire face with juices. When she released me, I took a big gasp of air.

"Yes! Oh, I made him cum on me... he came on my face!" I said, worrying a bit how loudly I'd blurted it, before finding myself nearly blacking out as Debbie surged to her feet and began humping her pussy furiously on my face. I had one hand on her ass and the other one dove into my panties as she held my head with both hands and ground herself until she came with a loud moan. I made a muffled groaning noise as I jerked and spurted cum all over my hand and her panties, and I was sure the entire house must have heard us by now.

I sank down onto the floor, breathing hard and my heart thumping, as Debbie sat back on the bed and smiled down at me.

"Well that was something, wasn't it?" she said. Her face was flushed and she had an almost manic look of excitement in her eyes. "Do you want to do it?"

"What...?!" I whispered.

"You fucking do, don't you?" she said in a low, dangerous tone. "Oh my god."

-----

Once Debbie had an idea in her head, it was always one-way traffic. For the next week, she was constantly in my ear about how well I'd played the role of "Ally", and how hot it would be to see the real thing acted out in front of her. I had started a casual job at the supermarket for the holidays, so I had a bit of time to myself, but that only seemed to give her more time to plot.

I got home from work on a Tuesday night, tired, and Debbie was at my place looking very excited about something. She was chatting to my mum in the kitchen when I came in, but quickly made an excuse for us to sneak off. In my bedroom, she pulled out her phone and showed me that she'd managed to get Ally to share the same video with her.

"It's pretty awesome," she said, "Ally reckons it turned her on... you watching her blowing your best friend. She wanted to know if you got horny seeing it."

"Fuck's sake... what did you say?"

"Oh, this and that," she said with a smirk. I had the awful feeling she'd shared a whole lot more with Alison than I wanted to know about.

"So anyway..." she said, and I sighed and put my head in my hands. I'd tried to explain I had no interest in her crazy idea, but she seemed to be almost in heat with the whole concept. I couldn't help be a bit excited by how much it was turning her on, but was resisting getting drawn into something which would ruin my best friendship. I flopped onto my bed and tried to ignore Debbie, but she lay down next to me and started watching the video with the sound on.

"Turn it down for christ's sake!" I said, worried my mum would overhear. Not for the first time, I wished I could figure a way to move out of home already.

"Wow, he's really thick isn't he?" said Debbie. "Poor Ally, she's struggling!"

I tried to ignore her and not look, but she slid a hand down, discovered I had an erection, and giggled.

"Are you sure you don't want to watch?" she said, "It feels like you do!" She started rubbing me through my work pants, and I couldn't help responding. I put down my own phone and glanced over, and had to admit it was very hot to watch the video a second time with my girlfriend rubbing my cock. I started to thrust gently against her hand, in time with the rhythm of Lucas' cock sliding in and out of Alison's mouth.

"Here, hold this," she said, passing me the phone. Her hand continued to grip me through my pants and her free hand dove into her tracksuit pants, followed by delicious wet sounds as her fingers dove into her cunt and began working in and out. I put one hand over the top of her pants so I could feel her masturbating herself, and she turned her head towards me so she could breathe into my ear.

"God Tom, I wish that was you sucking him off. I'm so wet thinking about it. Help me fuck myself!" she said, and I pressed firmly down on her hand as she worked her pussy.

"Talk to me, baby, tell me it's you!" she gasped, and I was so worked up I went with it.

"That's me, Deb, fuck... it's me... on my knees," I said.

"Baby what have you got on? You look so slutty".

"Pantieeeees," I groaned, getting very close to coming.

"What's in your mouth baby?"

"His dick... his big... cock."

"Whose dick? Tell me who you're sucking off with your mouth?"

"Luke... it's Lucas... I'm sucking him off, oh god...." I squeezed my eyes shut as my hips bucked and a hot jet of cum erupted in my pants, and next to me I felt Debbie spasm as she came at the same time.

-----

I was a bit defeated after that incident. For the next few days, Debbie kept making me play out one version or another of the same scenario. I found myself dressed in her panties, kneeling in front of her, going down on her while she pretended to be Lucas, and being made to play "Ally" with the most outrageous set of lines Debbie could come up with. And the thing was, it was getting to me. The more I played the role, the hornier I got. I was barely in my room for a minute before we'd be stripping off and dressing me in Debbie's lingerie, and she even made me put on one of her skirts and lipstick. Despite feeling like I was headed down a really bad rabbit hole, I felt like I was coming faster and harder than I'd ever done.

On the Friday night, she swiped a cucumber from the kitchen and used it as a pretend dick, making me suck that off while moaning and calling myself a dirty slut. When she was satisfied that I'd given her a good head job, she forced me to bend over the bed, pulled the panties down, and started teasing my ass with the wet vegetable. "Do you want me to fuck you now, Ally?" she asked.

I froze a little, even though I was incredibly horny. We'd done a little bit of ass play before, but the furthest it ever went was her fingering me a little way while giving me a blowjob. The cucumber was huge by comparison, but I also couldn't help pushing back slightly with my ass, wanting Debbie to finish degrading me completely.

"Oh you do, honey, don't you?" she said, and I turned my head into the sheet in embarrassment as she opened the bedside cupboard and fished out our lubricant. There was the snap of the cap, then a shivering cold feeling as she drizzled it onto my crack. Then I felt the cucumber inserted between my cheeks, smoothing the lube around. "Spread your pussy, Ally," she said quietly, and I reached back and did as I was told, feeling the tip meet my asshole. My whole body shuddered and jerked, and then I felt a steady pressure as she began working it into me.

"Oh baby, take that cock up you... yes... ssshhhhh," she said as my ass began to relax and open slightly. I made a pathetic mewling noise as the cucumber pushed through the resistance and began sliding into me, stretching my anus.

"Oh my god," I gasped, but she slid it back out and paused.

"Do you want it?"

"Yes! Do it!"

"What will you do for me, baby?" she said. "Will I get what I want?"

"Wha... what is it?" I said, but she just laughed.

"You know exactly, you little slut. Tell me."

I knew my face must have been crimson with shame at this point; wearing her bra, her panties around my ankles, my ass spread open in the air desperately wanting to be penetrated. I wanted and needed it, but knew she wasn't going to do it unless I caved in. And then I did.

"I'll suck him off.... Please Deb... whatever you want. I'll dress up..." The cucumber found its way to my puckered hole as I said it, and I groaned as she forced it back inside me.

"Oh god... oh god.... FUCK!" I groaned, erupting cum all over my bed as I felt my sphincter clenching rhythmically around the vegetable. When I'd finished, Debbie gently withdrew it, giggling when I accidentally made a small wet-sounding fart. I turned over and sank down onto the floor with my back against the bed, feeling a trickle of lube run out onto the carpet as I sat down. My eyes were closed as Debbie leaned over me. She pressed something into the sheets, and then squatted down next to me.

"Open your mouth," she said, placing a hand under my chin and digging firmly into both sides of my jaw. The strong stench of cum and ass filled my nostrils, and my eyes shot open. But before I could react, she had inserted the slimy vegetable deep into my mouth. My lips and tongue automatically pressed against it, giving me a nasty first taste of my load, before I could grab her wrist and force it back out.

Debbie laughed. "Don't worry - you'll be used to it in no time, honey!"

-----

I'd like to say that after this, I sobered up about the whole situation and laid down the law to Debbie, but somehow the damage had already been done. I'm not sure if it was me reacting to Debbie being so turned on by the idea, or the roleplaying we'd done, or crossing some invisible line taking a vegetable up my ass, but after that incident, I couldn't seem to think straight anymore.

And Debbie didn't even force my hand. Lucas' folks were away again, and we stayed at his place on the weekend. We spent the Saturday eating, drinking and lying by the pool, and she made no mention of any of it. But I couldn't stop thinking about how I'd played the role of Alison, and thinking very wrong thoughts about it. Was a cucumber similar to a cock? Would it feel different? Was Lucas' thick penis way too big? Every so often I'd be in conversation with him, or watching him walking around in his board shorts, and wonder guiltily if he could read my mind.

When we went to bed that night, I found myself with a raging hard-on that I couldn't hide, and Debbie smiled when she noticed.

"What are you thinking about babe?" she said, and I gave up trying to hide it.

"I think that I want it..." I said quietly.

"Yeah? Tell me exactly though. What do you want to do?"

"I want to go down on him."

"That's so cool!" she whispered, and gave me a very passionate kiss. When she broke it off, she took my chin gently in her hand and smiled. "I can't wait to see it. If you're lucky, we can kiss like that right after, too. Would you like that?"

"Oh god," I said, and scrambled to get her clothes off so I could fuck her. She giggled in excitement as I humped madly into her and came in what seemed like seconds.

When I woke up the next morning, Debbie was out of the room, and I could hear her talking with Lucas in low voices down the hall. After a while, she came back and saw that I was awake. She was only wearing a t-shirt and g-string panties, and when she sat cross-legged on the bed it left little to the imagination.

"Were you talking to Lucas in that?" I asked, a bit taken aback.

"Yeah... and I made sure he got a pretty good look babe. I think he liked it."

"Oh"

"Anyway I've got better news for you - I think maybe Lucas is less shy than what you'd think."

"Err... OK. So what were you talking about?"

"Oh easy - I asked if he was into threesomes, and he got my drift pretty fast."

"You did?"

"Yeah... I reckon someone had to break the ice, or we'd be skirting the issue forever. Want to hear about it?"

I nodded without saying anything, mainly because my mouth was suddenly very dry.

"Basically, I told him we're feeling pretty bad about him not getting any action, and suggested he might like to join in."

"But..."

"But... nothing much. I asked what he's up for, and he was mainly concerned you would freak out! So I looked him right in the eyes and told him you want to suck his dick."

"Jesus!"

"Well you do, don't you?"

"Yeah but... well, he'll think I'm a total fag now. Oh man."

She shook her head in amazement. "Tom, first of all, you're at least a bit bi at this point, aren't you. Or want to be. And second, it's just friends having fun. We'll keep it safe and secret. Also, I promised we'd play the girls to make him more comfortable."

"Oh... jeez." I contemplated that. "What... like, when are you...?"

Oh I'm ready when you are sweetie! Honestly, I've been looking forward to it long enough. Maybe you can have a shower and get dressed, and we'll have a pretty fun morning.

Next thing I was sneaking into the bathroom with Debbie, her armed with an armful of clothes, and then she insisted on joining me in the shower. Which I discovered was so she could help me shaving. "Guys like it smooth, you know!" she grinned, and went to work with a can of shaving cream and safety razor. It took a while, and I had to resist the urge to jerk off as she moved from my legs to my armpits and then to my balls and ass, making me super hard.

When we'd dried off, she produced one of her lingerie sets - a black lace bra and panties, with a matching garter belt and fishnet stockings. It was all I could do not to cum while she was assembling them over my newly shaved skin, and when I was dressed, she stood back and admired me.

"Mmm... hang on," she said. "You'll look much cuter with glossy lips. Especially with cum on them." With a grin, she fished out her lip gloss and held my face still while she applied it.

"Well?" she said. "You ready?"

"Not at all," I said, starting to tremble in panic.

"It's OK honey, I'm going to help you. Let's get some breakfast."

Debbie for her part hadn't bothered to change, and as she led me out of the bathroom and down the hall, her firm ass was on clear display every time her t-shirt shifted. I followed her with an erection tenting the black panties, feeling deliciously sexy and completely terrified all at the same time.

We found Lucas lounging outside in his board shorts, sipping a coffee. Debbie slid the screen door open and led me outside, and his eyebrows shot up in surprise.

"Woah! Uh... holy shit!" he said, half-laughing but not unkindly.

I stood awkwardly, crossing my arms over my chest and wishing my small cock would stop making my excitement so obvious.

"She's hot right?" said Debbie.

"She?" said Lucas.

"Ha... yeah. We can't have you fooling around with guys now, can we. This is... mmm.... Katie. Katie, this is Lucas!"

He nodded slowly, and I looked at the ground to avoid saying anything.

"Well... you two are the life of the party, aren't you?" said Debbie. "Lucas you might want to come inside."

She took me my the shoulder so she could turn me around and push me back into the house, giving me a smack on my ass as she did it. I stumbled slightly, my face going red.

Debbie led me to the living room with Lucas trailing after, and had me sit down on the couch. It occurred to me this was the same spot we'd caught Lucas screwing Alison that day, and now I was sitting there dressed up as a girl and not quite sure what I was in for. Debbie stood next to me and beckoned Lucas over, and as he approached, I saw his cock was hard, making his shorts stick out obscenely at the front. He walked over to Debbie, and she pulled him close to her, whispering in his ear in low tones that I couldn't quite make out. As she did it, her hand slid down his chiseled stomach and inside the band of his shorts, and then she pulled swiftly and revealed his cock in all its glory, barely inches away from my face. His shorts fell to the ground, and Lucas stood over me, completely naked, and with my girlfriend running her hands softly over his body.

Debbie paused and took her t-shirt off, shamelessly presenting her large tits to Lucas, who reached up to fondle them gently as she took his cock in one hand. Then she slowly sank to her knees, still holding him, and looked over at me. Without breaking eye contact, she leaned forward and kissed the head of his cock, a small, sexy smile on her face as she did it. Lucas groaned softly.

Debbie began to gently suckle on the head, alternating kisses and small licks, all the time looking directly at me. Then she stopped and beckoned me with a finger. "Come here, Katie," she said. "Come on."

In a trance, I slid off the couch to kneel next to her, my face now centimeters from Lucas' wet cock. He looked down at us as she kissed me, one hand holding his penis and the other one reaching up to massage my nipple through the bra. Then she moved her wet mouth back to his cock, sucked it hard, and kissed me again, this time sliding her tongue into my mouth. I moaned into her mouth - almost a sob - and then my mouth was open and moving without her help, moving onto Lucas' fat cockhead, and I felt a man's penis in my mouth for the very first time.

"Oh, good girl," said Debbie softly, rubbing her hands all over my body.

"Mmmm," I moaned, closing my eyes and starting to suck and lick at my best friend's cock. It was beyond anything I'd imagined - both soft and rigid, huge, fat, and burning hot in my mouth, and as I began to cover it with my saliva, I knew there would never be any going back.

"Keep going, baby - god yes. Suck that penis for me," said Debbie.

Lucas began to thrust himself gently as I went to work, and Debbie took my hands and placed them on his ass and balls. "There, play with him. Play with those balls honey. That's it."

Before long, I was holding his balls firmly in one hand and using the other to help him thrust forward as I gagged myself trying to take more and more cock inside my mouth.

"God, you're really good at this, Katie," she said in my ear, "I think you can take it from here." She stood up and gave Lucas a brief kiss on the lips, before moving to sit on the arm of the couch, one hand absently drifting down to insert a finger into her wet pussy.

Lucas took my head in both hands, and began to force himself harder into my mouth, and I put both my hands on his muscular ass, feeling it flexing as he fucked my face. Me - well, 'Katie' seemed a better name for me at this point... Kneeling before him in my sexy black lingerie... Sucking him off... Fucking him with my face... Taking his big fat dick... Waiting for him to... oh man... my head spun suddenly as I felt myself shoot in my panties without even touching my dick - a long, strong stream of juice soaking the crotch.

I had to pull my head off his cock so I could breathe, ragged panting gasps, with drool running down my chin.

"You OK?" he whispered, and I realised it was the first he'd spoken the whole time.

I looked up and saw he had a look of concern, and felt a wave of emotion. "I'm OK, I... I came in my panties!" I breathed.

"Oh wow... I... I need to cum too," he said, with a pleading look on his face.

"Come here," I said, and took his cock in my hand to guide it back to my lips again. As it slid back into my horny mouth, I tasted the strong sweet taste of his pre-cum and new he must be close. I began to suck as hard as I could, running my hands over his ass, pulling him into me, and he began to make small whimpering noises.

"I'm... I'm going to cum!" he said, pulling back to avoid it happening in my mouth, but I clamped my hands on his ass to top him, and locked my lips around his shaft.

"Mmmmm" I moaned, and then felt him convulse. The taste of his cum seemed to fill my mouth and nose in advance, but then the hot jets of it were erupting inside, and it was heaven. I reflected later that the cum itself didn't taste so nice - it had a slightly nasty aftertaste and got stuck in my throat and teeth. But the experience of suckling on his penis as he came in me was so exciting that I felt I might cum a second time. I realised one of my hands had gripped his shaft and was slowly masturbating him, squeezing the whole load out into my mouth while we both made small grunting noises. I snorted air through my nose to try to keep breathing.

Lucas finished, his cock softening just slightly as he pulled it out, and then Debbie appeared kneeling in front of me, still naked apart from her panties. Without speaking, she brought a hand up behind my neck and pulled me into a deep kiss, forcing my mouth open, her tongue probing and tasting the stickiness of his load mixed with my saliva. The smell and taste of his semen overwhelmed everything, and the room was quiet apart from the sloppy noises of us kissing.

As Lucas watched on, she broke the kiss, tilted my head back and drooled everything from her own mouth into mine. I knew what was required, and with my mouth almost full of the sticky mixture, I began to swallow it bit by bit while she smiled in approval.

I slumped back against the couch, gradually becoming aware again of my soiled panties and the sticky spots where cum had escaped and run down my chest. I panted and tried to clear my throat, watching as Lucas fetched his shorts and pulled them back on over his softening cock.

Debbie looked up at him.

"So - first threesome, hey?" she said.

"Yeah I guess," said Lucas thoughtfully. "Not the threesome I'd have imagined, I guess...". He looked over at me, clearly a bit awkward and unsure what to say. I imagined the post-nut clarity on this one would be an all-timer, but right then, I just felt completely happy. Slumped on the living room floor, dressed in lingerie, my stomach swimming with my best friend's cum.

"Well not the last, I hope," said Debbie. "Anyway - I haven't even had any breakfast."

And like that, we had to get up, get showered and dressed, and go about the day. But as she predicted, it was only the beginning of a very crazy journey.