Date: Fri, 17 Jun 2022 21:27:43 +0000 From: Trevor Metcalfe Subject: Theo's more than just a mass debater - Bisexual - Young friends Can I please remind all readers that this site only exists through donations. So please if you enjoy reading this or any other stories on the site, please consider making a generous donation. The following short story is set in current day England. It is based on the real life adventures of a friend of my grandson's, with a little poetic licence thrown in. Theo was 14, an intelligent lad, which some people found off putting. He was in the school chess club, enjoyed the occasional game of tennis & swimming, but his favourite activity was debating. He had set up a school parliament & debating society, with his main ambition in life, becoming a politician. Theo was a little under 6' tall & skinny, he had short blonde hair & blue eyes, with a minimal amount of muscle growth in his upper torso. When it came to his penis, that was just a little impressive, flaccid it hung down over his scrotum about 6", however when erect it thickened up, but only grew an extra inch in length. His sexual experience with girls was zero, he did however have a wank buddy, Andy who was 13yo & a quiet lad. They had progressed to wanking each other & Theo was hoping they would move onto cock sucking in the near future. Having won several debate competitions, Theo's school team were selected to represent the county in a national competition for ages 13 to 17. The event was being held in Manchester, over a bank holiday weekend, which meant staying for a few nights in a hotel. Theo's team was himself & 3 girls, a 13yo & 2 x 16yo's. This meant that the three girls shared a family room & Theo had a double room to himself. They were also accompanied by a teacher Mrs Collins, she was somewhat pissed off at losing her long weekend, so had secretly invited her husband to join them & once he arrived, the students hardy saw anything of her. The first night there was a reception, a dull event designed to allow the competitors to meet each other. The competition itself would take place over the next couple of days. Theo didn't really do parties, so by 9pm was looking for an excuse to slope off. Filled to the top with pop, Theo needed the toilet. He couldn't be bothered to go back to his room, so went into the lobby toilets. There was a young boy already in there, standing at the urinal, his hand moving up & down his erect boy cock. Theo stood close to the boy & pulled his dick out. The young lad's eyes were out on stalks. "Wow ! You have got a really nice cock". "Thanks". Theo went on to introduce himself & the lad reciprocated. His name was Toby, he was 12yo & at the hotel because his older brother was in the competition. Toby then angled his body towards Theo, giving him a much better view of his dick. Theo guessed that it was nearly 5" in length & he could see a small bush of pubes at its base. "Theo, if you like we could go into a cubicle & I'll suck you off". Theo was amazed at the openness of Toby, he could never be that forward with a possible partner. "I have my own room, wouldn't it be better & more private if we used that" ? Theo shook off his dick, getting rid of the last few drops of pee. "Awesome, lead the way". When they reached the room, Toby, who was just wearing shorts & a `T' shirt, stripped off within seconds & threw himself on the bed. Theo however was wearing his school uniform as instructed by the headmaster before they left. As ambassadors for the school, they were expected to wear uniforms during the competition & at any functions. Theo began removing his tie & unbuttoning his shirt, However, Toby was far too impatient for all this faff & pulled Theo to the bed, so that he was standing in front of Toby. He immediately pulled down his fly zipper, pushed his hand inside & pulled Theo's dick out through the slit in his boxers. Leaning forward, Toby took Theo's excess foreskin between his lips & rolled it around, causing Theo to moan. Next, Toby peeled back Theo's foreskin, revealing his pulsing knob, then he swirled his tongue over every mm of Theo's head, causing it to harden instantaneously, "Have you done this before Toby" ? Toby released his oral grip. "Yeah, I've done it many times with my brother". "No wonder you're so good at it". "Thanks". Toby returned to his task, running his tongue up & down Theo's hard shaft. He couldn't reach his balls, as they were still wedged in Theo's boxers, so he concentrated on his cock. He took it into his mouth, so that Theo's head was pushing against the back of his throat. He started to suck hard, driving Theo to the edge of ecstasy. He had been imagining getting a blow job for several years, but the reality was so much better. Looking down, he could see his erection poking out from his school trousers & Toby's head bobbing back & forth. He could feel his sap rising. "I'm gonna cum". Toby's mouth took a tight hold of Theo's cock, as he pumped wave after wave of his spunk straight down Toby's throat. Theo finally got undressed, allowing Toby to tickle his scrotum. "It's my turn to do you now". "Cool" "You'll have to forgive me if I'm not very good, it's my first time". "How about you lay on the bed & I'll fuck your mouth". "Sounds good, just don't go too hard". Theo moved on to the bed, lying on his back, Toby joined him, straddling his chest. He then shuffled forward & leant forward, pushing his dick to Theo's lips. "Ok, open wide". Toby pushed his dick into Theo's mouth, getting in deep enough so that his balls were bouncing against Theo's chin. He could already taste the salty pre-cum oozing from Toby's slit. Theo felt a little discomfort as Toby increased the pace, but was still able to take a hold of Toby's buttocks & give them a firm squeeze. Toby's breathing quickened & he released a deep groan. "I'm cumming, I'm cumming". Theo got his first real taste of boy cum, as Toby shot his load into Theo's mouth. They both relaxed, although Theo was very keen to go again. "What do you want to do now" ? "Sorry, but I better get back downstairs, my family will be wondering where I am". "Ok, thanks for a great time, maybe I'll see you over the next two days". "I hope so". Theo couldn't be bothered to re-join the reception downstairs, so just lay on his bed naked, reflecting on what had just happened. It had been his first real taste of sexual activity & he wanted more. With a huge smile on his face, he was drifting in & out of sleep, until after about an hour, there was a loud knock on the door. "Who is it" ? "It's Lotte". Lotte, AKA Charlotte, was the youngest member of the team at 13. "Hold on a minute". Theo ran around looking for something to wear, in the end he settled for a towel, which he wrapped around his middle. Lotte was a pretty girl, about 5' 6" in height, brown hair & eyes. However, she came across as a little staid & boring, not somebody you would be relying on for fun. Having said that, Theo was hardly gregarious. Eventually, he opened the door, to see Lotte with a holdall. "Can I come in" ? "Sure, but I was just going to have a shower". "That's ok, I'll wait". Theo wasn't keen on this idea. "What exactly do you want" ? "Can I stay in here with you for the next few nights" ? This request took Theo by surprise. "Why ? What's wrong with your room" ? "It's not the room, it's Chloe & Emma". "Why is that a problem ? I thought you got on well with them". "Generally, I do. But you know they're lesbians ? They just told me that I was getting the sofa-bed & then they immediately started kissing & scissoring. Chloe's clit was so swollen, it could probably be seen from space. I just feel so out of place". "I guess that must be very awkward for you, although I wouldn't mind sharing with them". Lotte gave Theo a dirty look. "So, can I stay" ? "I guess, after my shower I'll get the sofa bed sorted out. You can take the main bed & I'll sleep on the sofa bed". "Thanks. I really appreciate it". Theo went into the bathroom & locked the door behind him. His head was spinning, not knowing if this arrangement would work out. He took a long shower & finally came back into the room, still just attired in a towel. He was met by the sight of Lotte laying on the bed, wearing just a pair of skimpy panties. Her pert titties on full view & her nipples jutting upwards. "I've been thinking Theo, there's no need to get the sofa bed out, there's plenty of room for both of us in here". "Umm, are you sure" ? "Yeah I'm sure I can trust you, just not certain I can trust myself". Theo laughed nervously & sat on the edge of the bed. "Ok then, what side do you want". ? "Don't worry about that right now, why not lay beside me & we can talk". "Alright". Theo climbed onto the bed, holding his towel in place & laid to Lotte's right. She made a quick grab for his towel, but Theo had a tight grip on his only cover. "How about, I'll show you mine, if you show me yours". "Isn't that a little childish" ? "Don't worry, I won't laugh if it's tiny". "It's not that, It's ... oh what the hell". Theo wriggled out of his towel, exposing his cock to Lotte. "I'm impressed, that looks awesome". To keep her part of the bargain, Lotte lowered her panties down to her knees. She had a small, well-groomed bush, with a protruding labia. Without a word, Lotte reached over & took hold of Theo's cock, her hand felt so soft & it took just a few tugs to get him hard. Theo responded by pushing his hand between her legs, instantly feeling her wetness. Lotte continued to pull away at Theo's cock, causing it to jerk in her hand & making Theo moan. Theo in turn had discovered Lotte's hole & had inserted two fingers inside. "Oh Lotte, if you keep going any longer, I'm gonna cum". "Awesome, I won't be far behind you". Theo knew that nothing could stop him now, so he just laid back & let the orgasm take over his body. He shot cum further than he ever had before, the first two jets hitting him on the chin & as it began to subside, Lotte's fingers were covered in the last spillage. She looked at Theo, with a wide smile on her face & licked all the jizz from her fingers. Now Theo had to up his game, he had seen a guy licking out a pussy in porn films, so decided to try that. As he positioned himself between her legs, Lotte bent her knees, as his face approached her bush, he was overwhelmed by the musky aroma, taking a few deep breaths, to take it all in. As Theo closed in, he targeted her clit, circling it with his tongue, he also pushed a finger deep into her tight hole, which really got her moaning. "Oh yeah ... oh yeah .... Fuck that feels amazing". Lotte's back arched off the bed, as an orgasm devoured her petite body & her pussy went into flood, creaming in Theo's face. They laid side by side, naked & holding hands. "Theo". "Yes Lotte" "Are you a virgin" ? "Yeah". "Me too, do you want to lose it with me" ? "I suppose, I don't think I've got anything better to do". "You cheeky little rat". "Yeah, but I'm adorable". "We'll see about that". Theo rolled over, pinning Lotte to the bed. He put his hand down between her legs & could feel that her pussy was still dripping. Theo's cock felt harder than ever, as he poked around Lotte's cunt. Eventually, the head of his cock was pressing against her labia. "Are you ready" ? "God yeah". Theo pushed forward, entering Lotte's slippery, tight hole. However, he quickly met some resistance. "I think something's wrong, there's something blocking my from going any deeper". Lotte laughed. "That's my hymen you idiot, you have to push harder to break it". "Oh, I see". Theo was embarrassed by his naivity, but did as he was told & pushed harder. Lotte's hymen gave way & Theo's cock slid deeper into her pussy. Lotte let out a yelp, nothing had gone this deep inside her before. Her pussy tightened around Theo's cock, like a leg in some skinny jeans. Worried about the yelp, Theo pulled straight out & noticed some blood on his cock. "Oh god, are you alright, have I hurt you" ? "No I'm fine, we were told to expect some bleeding first time". Theo gave a big sigh of relief. "Is it ok to carry on" ? "Yeah, see if you can get it all inside". Theo thrust back into her pussy & with each push moved further into har welcoming cunt. With every push Lotte's moans got louder, for a second Theo worried that the adjacent rooms would hear her, but then quickly decided that he didn't care. Each thrust was bringing him closer to climax. "I'm nearly there, do you want to pull out" ? "No, if you hold on a few more seconds, I'll join you". Theo began to go over tomorrow's debate speech in his head, anything to distract him. Meanwhile, Lotte's face reddened & her breathing rate increased, then suddenly she started to shake violently. "I'm cumming, I'm cumming". She shouted loudly. With this her muscles contracted, causing her pussy to grip Theo's dick even tighter. This pushed him over the edge, with a deep sigh & some jerky movements, he planted his seed deep inside Lotte's pussy. They lay together recovering from their first fuck, then Lotte leant over & kissed Theo. "Thanks, that was amazing". "That was the best thing ever". After a break, they went for it a second time, with Lotte riding Theo's cock, causing his 4th orgasm of the evening. Eventually, they got some sleep, Theo was spooning Lotte, his flaccid cock resting against her butt crack. The following morning started with some hard, fast & very soapy shower sex. The day continued well, when Theo & his team won their morning debate. Then at lunch Theo was approached by an older boy in school uniform, who introduced himself as Danny, Toby's older brother. They had been chatting for a while when. "Toby told me that you had some fun together last night". "Yeah, he's very enthusiastic". "Do you think we could both come to your room after dinner tonight" ? "Umm, that would be so cool, but things have changed since I met with Toby last night". "How's that" ? "I've inherited a room mate since then, she's one of my teammates". "You're sharing with a girl, have you fucked her yet" ? "A gentleman never tells, but yeah". "Do you think she'll mind if Toby & I drop by later" ? "I'll ask her later & let you know at dinner". "Cool, I'll catch you later". Again, Theo & his team won their afternoon debate, so were on a high. Theo & Lotte went back to their room, to get ready for dinner. "Theo, have we got time for a fuck" ? "Yeah, but I need to tell you something first". "Ok, what's that" ? "I'm bisexual & last night before you turned up at the door, I had been having some with a lad called Toby". Theo paused momentarily. "Oh my god, that's so hot" ! Theo sighed with relief. "Anyway, Toby & his brother have asked if they can come to our room later, to have some fun with us both. What do you think" ? "Say yes, that would be amazing, I'd love to watch two boys getting it on". "Ok I will, now what were you saying about us fucking" ? The pair quickly undressed & Lotte was soon on all fours, feeling Theo's cock ploughing her pussy, doggy style. Theo found Danny in the dining room & told him the good news, they agreed to meet up at 9pm. Toby & Danny knocked on the door at exactly 9 o'clock & were let in by a half naked Theo. As they entered the main part of the room, Lotte was lying on the bed just attired in her underwear. "Hi I'm Lotte". "Hi Lotte, I'm Danny & this is my little brother Toby. Wow you look hot". Several knowing looks passed between them & within a couple of minutes, the three boys had stripped naked & were sporting boners. Danny had a 6" erection and was fully shaved. "Wow ! I never expected to see 3 gorgeous cocks together like this". A brief discussion followed about who should be doing what to who, until Lotte stated that she would love to see two boys having fun together. Theo & Danny top & tailed on the bed, putting them in a 69 position. Simultaneously, they grabbed hold of each other's dicks & rolled back the foreskins. Lotte was lying beside them & having unclipped her bra & kicked off her panties, she was now as naked as the boys. Toby was sitting at the bottom of the bed at Lotte's feet. As the two purple pulsing knobs were unsheathed, Lotte's hand went right between her legs, allowing her to push two fingers into her wet pussy. Toby was also gently stroking his boy tool with one hand, the other he was running along Lotte's ankle & calf. Theo & Danny were now running their tongues along the other's shaft. Danny then kissed Theo's balls in turn, causing him to moan & release some pre-cum. Theo had worked his way back up to Danny's head & was swirling his tongue around, as well as invading his cum slit with his tongue. This caused Danny's juices to make an appearance, as pre-cum oozed out. Lotte's engine was now revving. "Toby, why don't you lick out my pussy" ? "Ok". Toby didn't hesitate, he moved up the bed & buried his face between Lotte's legs. This was the first time he had been close to a pussy, so needed some guidance. Lotte helped by pulling her lips apart & pointing out her clit. Toby was a fast learner & soon had his tongue pushed deep into Lotte's pussy, tasting all those wondrous juices, as Lotte writhed around on the bed. Next to them, Theo & Danny were doing their best to `deep throat' each other, both making a mixture of moaning & sucking sounds. Eventually, Danny's leg seemed to spasm, then his whole body momentarily stiffened, as he fired many jets of cum into Theo's mouth, all of which was gratefully received. Lotte was next to succumb, she shook as her pussy creamed. As the orgasm waned, Lotte asked Toby to push his cock into her foaming cunt. This was his first time fucking a pussy, but there were no nerves, he positioned himself on top of her & thrust his cock inside. Beside Toby, his brother was still sucking hard on Theo's dick. Theo was showing signs that he was getting close, which encouraged Danny even more, although he did have one eye on his brother fucking Lotte & losing his virginity. However, Theo was done, he could feel the warmth & pleasure building in his groin, then with a final deep groan he shot wave after wave of his thick spunk into Danny's mouth. A few moments later Toby let out a squeal, his little white bum stopped pumping, as he shot his cum into Lotte. Theo & Danny now turned their attention to Lotte. Theo moved his face between her legs, he could smell the heady mixture of her creamy juices & Toby's boy cum, which was still oozing from Lotte's pussy. Danny, moved to Lotte's pert little boobs & began sucking her cherry red nipples. Toby was happy just to take a break & watch. A discussion followed between the other two boys, concerning who should fuck Lotte next, until she interceded. "Hey boys, why don't you both fuck me at the same time, like they do in porn films" ? "How does that work" ? Asked a slightly naive Theo. "One of you sticks it in my pussy & the other puts it in my bum hole". "Ok, but can I do your pussy" ? Danny had a reason for wanting to do this, as despite his bragging to his brother, he was still a virgin. Now his little brother had beaten him to be first in a pussy, he was desperate to be close behind him. "That's fine by me, if Lotte's ok with it" ? "Yeah, that's cool". It was decided that Theo should get things started by testing out Lotte's arsehole. She went to her bag & produced a tub of vaseline, which she said she used for `chapped lips'. However, she later admitted to Theo that she had brought it with her, hoping she would get to use it for anal sex. Lotte dipped three fingers into the tub, coating them with the lube, which she then gently rubbed into Theo's hard cock. Toby then jumped in & coated one of his little fingers, then inserting it into Lotte's butt. Theo then took position behind a bent over Lotte, took hold of her hips & eased his slippery pole inside. It was very tight to start with, causing Lotte's to wince in pain as his cock had travelled in about 2". However, Lotte quickly relaxed, determined to feel pleasure, which made it much easier for Theo, who now had most of his cock inside. With phase one completed, Theo was ordered to pull out & Danny told to lay on the bed, close to the end & on his back. Lotte had taken the `alpha' role, bossing the boys about. Danny did as instructed & Lotte straddled his lean body, facing Danny & her wet pussy easily devoured his 6" tool. Lotte then leant right forward, exposing her second hole to Theo. He didn't need a second invitation, he moved behind Lotte & slid his cock back into her arse. Lotte began to ride Danny's dick & Theo adjusted to her rhythm, pushing into that second hole. Danny was in heaven, not only was he in a soft moist pussy for the first time, he could also feel Theo's cock rubbing against his own. He was however restricted in movement, so just had to lay back & let it all happen. The stimuli was intense & he just couldn't last any longer, firing his seed into Lotte. She wanted more though, wanting two cocks inside her, making her cum. She therefore kept riding Danny's cock, refusing to let it soften. At the same time Theo was pumping faster & deeper into her arse, bringing her to the edge of another epic orgasm. "Oh my god ... oh my god ... oh my god". Lotte's small body shook with ecstasy, as she was nearly ripped apart by another orgasm. It took Theo another 30 seconds to reach his climax, he pulled his cock out & shot several jets of his thick cum, along Lotte's spine. Toby wasn't going to be wasteful, he immediately moved to Lotte & greedily lapped up Theo's tasty spunk. Lotte rolled off Dany, leaving him lying back with a boner. Theo didn't want to waste this opportunity, so stood in front of him. He then raised Danny's legs, placing an ankle on each of his shoulders. There was no resistance from Danny, who was happy to let it all happen. Theo leant forward, pushing the head of his cock against Danny's ring. With a strong thrust, he pushed his cock several inches into Danny's hole, which made him gasp in a mix of pleasure & pain. It only took several deep thrust, to push Danny over the top, his cum flying out to land on his chest. Theo kept going for a few more minutes, before depositing his spunk in Danny's boy pussy. Meanwhile, Lotte noticed Toby sitting on the edge of the bed with a spare boner. She moved over to him & asked him to stand, so that she could sit in front of him. As he did, she grabbed hold of his arse cheeks, squeezed them & pulled him close to her. Lotte bent forward, taking Toby's cock in her mouth & at the same time, pushing a finger into his butt hole. This took Toby by surprise & made him howl seemingly in pain, but he was soon pleading with Lotte to carry on. Toby had been watching the other three for over half an hour, so was frustrated & ready to explode. Being sucked & fingered simultaneously, drove him mad with pleasure. So, Lotte was soon savouring the sweet taste of Toby's cum. Danny & Toby left having had two hours of solid fun. Despite feeling tired, Theo & Lotte managed to fuck twice more that night. The following morning, Theo awoke early excited about the debate final later that day. Lotte was fast asleep, so Theo decided to go for a swim to clear his head. The hotel had a small pool & gym down in the basement, so that was Theo's destination. When he arrived there was only one other person in the pool & to his surprise it was Mrs Collins his teacher. "You're up early Theo, is everything ok" ? "Yes Mrs Collins, I just thought I would blow away the cobwebs. How about you" ? "Please call me Susan. I was just hiding from my husband's snoring". "Ok Susan, I better get my trunks on". "Don't bother on my account". She laughed, but Theo thought it was a little strange & sexual, but he laughed it off. He went off and quickly changed. They swam together for about half an hour, occasionally stopping for a brief chat, then got out at the same time. Going to their respective changing rooms. Theo just sat there for a while, eventually deciding to have a quick shower there, rather than going back to the room. Whilst there were separate male & female changing areas, the showers were open to all, so the vast majority of people kept their swimming costumes on. Theo walked into the shower room wearing his trunks, but was met by the sight of Mrs Collins showering stark naked. She was hardly the most attractive of women, in her early 40's, short & chubby, but with huge tits. "Come & join me, the water's nice & hot". "Yeah, ok". Theo tentatively stepped into the shower, as Mrs Collins looked him up & down, examining him as a lion examined its prey. Then pointing to his trunks. "You don't need those on, there's only us two in here & I've seen it all before". "Um, err, I suppose". Theo slowly pulled down his trunks, revealing all. "I heard you had a nice penis & that you've been poking Charlotte for the last two days". Theo began to redden & replied in a nervous voice. "Where did you hear that" ? "I'm sure you could guess, don't worry though your secret is safe with me". She moved over to him & placed her soapy hand on his cock. "What are you doing Susan" ? "Sorry, I thought you would like it". "It's nice, but you're my teacher". "Have you ever had a `tit wank' Theo" ? "No". "Well, that's something I can teach you". Both still wet, Susan led Theo into the female changing room. She then laid on her back on the table in the middle of the room & instructed Theo to straddle her middle, kneeling down. It was a tight squeeze on the table, Theo nearly fell off the first time. As he edged up the table, Mrs Collins moulded her huge jugs around Theo's hard cock. He rocked back & forth pushing his cock into her cleavage, she continued to massage his dick with her big boobs. They both knew this was wrong, but Theo was actually starting to enjoy it. He could feel the orgasm building inside him, then without warning he ejaculted. Several thick ropes of his cum shot across Susan's face, one going up her nose. They began to clean up, when Susan blew her nose & Theo's cum shot out, which made them both laugh. They then heard voices coming down the stairs towards the pool, so Theo put his trunks back on & hurried back to the male changing area. These events were never repeated or even talked about again. Theo & his team won the debating final & went on three months later to Geneva in Switzerland, where they represented England in the European finals. The End. As always with my stories, I welcome any feedback (good or bad) + any constructive criticism. I'm also happy to chat with like-minded people & maybe exchange personal stories or material.