Disclaimer:The characters in this story belong to Greg Berlanti and are the property of Berlanti-Liddell Productions, Shoe Money Productions and Warner Bros Television. This story is for entertainment purposes only and I do not make any money from it.
summary:Jack And Bobby both have some new experiences with the ladies in their lives
category: Transgender/she-male
It was just another day at school for Bobby Mcallister, at least it was until he saw his former crush Dina wearing an incredibly short black miniskirt, his attention was immediately drawn towards her tight ass, he was starting to get turned on. And then it only got worse when Dina bent over to pick up a bock she had dropped and Bobby caught a glimpse of her sexy red panties. Bobby was getting painfully hard at this point so he ran in the direction of the bathrooms but ended clumsily tripping and falling right in front of Dina, Dina immediately noticed him and said "hi Bobby" in a sweet voice that further turned him on, "are you okay?" asked Dina as she helped him up, "yeah i'm fine" Bobby responded. "why?". "Cause you got quite a bulge there!" Dina laughed, Bobby turned bright red upon hearing her say that, "don't be embarrassed" Dina remarked, "I think it's cute that you find me that attractive" "now how would you like me to take care of your "problem?" Dina asked in an extremely sexy voice that nearly made Bobby cum in his pants. Bobby couldn't believe what she had just asked him, he couldn't form words so he just nodded quickly, "well then let's go in that closet at the end of this hall, Dina suggested, no one uses it anymore" Bobby instantly grabbed her and ran off to the closet, where they went into a dark dimly lit corner. Dina immediately started stroking Bobby through his pants causing him to groan loudly, she then slid hand down into his pants and started stroking his cock and balls, causing him to moan with reckless abandon, Dina then got impatient and tore off his pants and boxers and took his cock into her warm wet mouth, causing Bobby to moan with pleasure and close his eyes,Dina was really enjoying the taste of his cock and was eager to taste his seed, so she suck Bobby as fast and hard as she could, causing him to groan loudly and shoot his sperm in her mouth, Dina loved the taste of it and savored it for as long as possible.
Bobby was dumbfounded at what had just happened and then asked "why did you do that?" "cause I felt like it" Dina responded with a sexy grin "I miss being with you". "Yeah, I missed it too" Bobby responded, "so can I eat you out?" he asked boldly. Dina was surprised to hear him ask that, "sure thing" she said eagerly and promptly tore off her skirt, panties, shirt and bra, leaving her nude, Bobby took a moment to admire her beauty before diving and eating her out like crazy, Dina then tightly gripped his ass as she gasped loudly, Bobby then started pinching her erect nipples as well which quickly sent over over the edge and she came all over his face, Bobby couldn't believe how good her cum tasted, it tasted better than anything he had ever eaten or drank. Dina was exhausted from her orgasm and didn't think she'd be able to get up, until she heard the door open and she suddenly jumped up and started trying to get dressed, "don't bother putting those back on just yet" a sexy voice said, Bobby immediately recognized the voice, "Dex"? Bobby asked, "what are you doing here?" "this is where I come to smoke everyday" Dex responded, "but it looks like i'll be doing something a lot better today" "what are you talking about?" Dina asked apprehensively, "I'm talking about making this a threesome, duh" she laughed, "hope you don't mind" "oh no I don't mind!" Bobby quickly responded, he couldn't believe how lucky he was today, getting a chance to have sex with both of his former girlfriends! "What about you?" Dex asked Dina, "well I have always been curious about having sex with a girl". Okay then, let's get this party started!" Dex exclaimed as she tore off her shirt and bra and started hotly making out with Dina, Bobby was soon hard as a rock again after witnessing his girlfriends making out, he then took off his shirt and hesitantly pushed his cock up Dina's ass, Dina gasped at the sudden intrusion and moaned "fuck me harder!" Bobby obeyed and started hammering his cock in and out of her ass like a piston, Dex then asked her "how you'd like to get double stuffed"? "what?" Dina asked confused, Dex then removed her black jeans and black silk panties revealing a rapidly hardening cock!
Bobby and Dina were shocked at the sight and didn't know how to respond. "this is the reason why i've never had a lasting relationship with anyone" Dex responded "they always freak out at the sight of hermaphrodite" she sighed, "well I still think you're hot" Bobby remarked, "yeah me too"! chimed in Dina, "in that case, I hope you're ready to get your cherry busted" "actually I lost it horseback riding" Dina responded, "too bad, I was hoping to be the one" Dex said, "oh well" Dex then rammed her cock up into Dina, causing her to shriek loudly, "keep quiet will you!" dex hissed, you want the whole school to hear?" "why don't you put these in your mouth?" Dex asked holding up her cum soaked panties, Dina stuffed them into her mouth and Dex and Bobby went back to pounding her relentlessly, soon they all started feeling the need to orgasm, but it was Dina who broke first, she bit down into the panties hard ass she moaned loudly, Bobby felt her tight ass clench around his cock, causing him to shoot his seed deep in her ass, Dex soon came as well, as the feeling of Dina's pussy clenching around her cock was too much and she shot a huge sticky load up her cunt. "Will this make me pregnant?" Dina asked worriedly, "nope, it's not possible for me to do that" Dex responded, "that's a relief" Dina sighed. Despite her orgasm Dex was still horny so she asked Bobby, Wanna lose your virginity to me?" "if it's okay with Dina that is?" "it's fine" Dina said, she was your first girlfriend so it's only fair", "oh yeah!" Bobby exclaimed as he rammed his cock up her pussy and started pumping rapidly, Dex groaned at how good it felt as she hadn't had sex in a very long time, she then got a another idea, "hey Dina!" she asked, "would you mind sucking my dick?" "hell no!" she responded eagerly as she gently licked the tip of Dex's hard dripping shaft, causing Dex to bite back a howl of pleasure, Dex then quickly stuffed her panties in her mouth to keep quiet, Dina was spurred on further by this and took as much of her cock as possible into her mouth and started licking her all around while Bobby repeatedly slammed into her moist cavern with all his might, this was too much for Dex as she bit back a loud muffled moan as she shot her hot load down Dina's throat and her pussy gripped Bobby like a vice, causing him to lose all control and shoot a big load into her. They we're all exhausted from the experience and quickly got dressed, "wait a minute" Dex said before you leave, ``I want to make one thing clear to both of you" "if you EVER tell anybody that I have a dick, "then you're gonna both be VERY sorry!" she said menacingly, "don't worry, your secret's safe with us Bobby and dina said. "Good, and in case you're wondering, no I can't get pregnant" she said. "so, same time tomorrow?" Bobby asked, "Sure thing!" Dex said with a grin, all 3 of them then hurried to their next class before anybody got too suspicious.
Jack Mcallister had just seen Bobby emerge from the never-used utility closet along with Dex and Dina, by looking at their disheveled hair, it was all too obvious what they had been doing. Jack was stunned that his 14 year old brother had managed to have a threesome before he did, though he should have been concerned that his younger brother had just done something illegal, he was too jealous to really think straight. It had long been a fantasy of his to have sex with Courtney, Missy, and Katie all at once, he was sad that Missy never got to have the experience before her untimely death. But today, Jack was determined to get Both Courtney and Katie. He first asked Courtney during Study Hall if he she would ever have sex with another girl if given the chance. "I don't know" she said uncertainly, "i've never really thought about it before" "but i'd be willing to give it a try", "why are you asking"? she inquired. "Cause I was hoping i'd be able to have a threesome with you and Katie" Jack said hesitantly, "I wouldn't mind trying it out, "but i'm not sure if Katie will go for it" Courtney remarked. "Well it's worth a try," Jack said hopefully.
Jack wasn't able to catch Katie until after her biology class, he hesitantly walked up to her and said hesitantly "Katie, can i ask you something" Katie got a dark look in her eyes and responded angrily "ask me what! if i'm okay with the fact that you don't talk to me anymore since you've been dating Courtney!" "Well I got the feeling that you didn't want to see me again after you saw Missy kissing me" Jack remarked with a hint of annoyance. "I got over that as soon as I heard Missy died, "I felt really guilty cause I was sort of hoping something bad would happen to her" Katie said, biting back tears. "i'm mad cause you never bothered even trying to talk to me after that day, and I figured if you really cared about me you would have at least attempted to apologize to me or something" "I wanted to, but after I started dating Courtney, i sort of forgot about everyone else, and I figured you would've said something if you really cared" Jack countered. "Well let's just both say we're sorry then" Katie said, having calmed down, "because i really miss talking to you, no one else understands me the way you do", "now what was it you wanted to ask me?" she inquired. "well, I wanted to know if you would ever have sex with another girl" Jack asked nervously. "I have had sex with other girls before" Katie replied nonchalantly, "though I haven't done it for a while now" "Any particular reason you're asking me this?". "Well actually, I was wondering if you would have a threesome with me?" he asked hesitantly. Katie's eyes widened when she heard the question, "sure why not?" she said, suddenly getting a huge grin on her face, "who else did you have in mind?" she asked eagerly. "Well I already asked Courtney, "and she said she was willing to try it out", "that sounds okay with you?" Jack asked. "Oh you bet your sexy ass it is! she said excitedly, "I've always wanted to have sex with her but I never had the courage to ask her" "Well in that case" "when and where should we have this encounter" Jack asked eagerly. Why not right now?" Katie asked sexily, ``it would beat the hell out of listening to another boring History lecture". "Yeah, I guess skipping one class wouldn't be so bad, we can just duck out of school afterwards since it's the last class" "Sounds like a plan" Jack said huskily "now let's find Courtney, "her Math class should be finished now".
So the two of them quickly found Courtney and Jack led them all to the same closet Bobby had gotten lucky in. "You sure we'll be safe?" Courtney asked hesitantly. "yeah, we'll be fine" Jack said reassuringly, "none of the staff uses this room anymore". "okay, then lets get this started" Courtney said with a sudden burst of excitement, she then tore off her shirt and started kissing Katie full-on the lips, Katie was taken aback by this for she was not expecting Courtney to be so bold and eager. Katie then eagerly returned the favor while Jack had already stripped down to nothing and was slowly stroking himself while watching his girlfriend and ex-girlfriend making out and groping each others breasts. Katie then decided to take things a step further and unhooked Courtney's bra and started licking and sucking her breasts slowly and softly, Courtney was so turned on by this that her green bikini panties we're feeling very sticky, so she peeled them off and removed Katie's jeans and shirt and was stunned to see a bulge in Katie's black lace panties,"you have a dick?" Courtney asked in shock, "yeah, that doesn't bother you does it? Katie asked nervously, "are you kidding?" Courtney exclaimed, "i'm even more turned on now! Katie was incredibly horny and wanted to cum long and hard, so she asked Courtney "want to try a 69?" Courtney jumped at the idea, "you don't have to ask me twice" she responded eagerly, both girls then got into position and licking and sucking each other like crazy, Jack couldn't take it anymore and immediately plunged his dick into Katie's ass, causing her to moan into Courtney's snatch making her moan around Katie's dick, they all soon started feeling their orgasms rising, though Jack was the first to go, pumping jet after jet of hot cum into Katie which started a chain reaction, causing Katie to bite Courtney's clit, which made her cum hard and moan loudly around Katie's dick, causing her to lose control and shoot her load into Courtney's warm wet mouth.
They all paused to regain their strength, and they we're soon very horny again, Katie then decided to be bold and asked Jack very sexily, "would you mind if I fucked you in the ass Mcallister? Jack wasn't too sure, but he decided to go along with it and nodded his head, Katie then thrust her 8 inch dick up his ass, causing him to feel a mixture of pleasure and pain, though the former quickly outweighed the latter. Jack then asked Courtney through clenched teeth, "want me to go inside you?" Courtney then grinned and spread her legs eagerly, and Jack eagerly rammed his cock inside of her, causing her to fight the urge to moan loudly, which she quickly rectified by stuffing Katie's panties in her mouth. the 3 of them we're fucking together in unison harder and faster, til Katie finally broke and shot her sticky cum up Jack's ass, the amazing feeling of having a shemale cumming in his ass as well as having his girlfriends pussy clenching his dick extremely tight, caused him to lose control and shoot his cum deep in Courtney, he knew she wouldn't get pregnant as she had been taking birth control pills since the incident with Nate. Courtney finally lost control and came harder then she ever had in her entire life. They all collapsed in a heap, not wanting to move. "wow that was amazing!" Courtney gasped, you guys are so much better then Nate. "Glad we could help" Katie said, grinning sexily, "I haven't has sex that good in forever" Katie moaned. "Yeah, I never thought I could get you two to agree to this in a million years" Jack remarked. "So why did you suddenly ask us then? Katie and Courtney both asked curiously. "Well today I saw my brother coming out of this closet along with both his ex-girlfriends" "and then I realized how long it was since I had sex, so I decided that if Bobby could have a threesome, "then so could I" Jack answered. "Bobby was having sex?!" Courtney exclaimed in shock, "doesn't that bother you at all?" "Nope, i was too jealous to be bothered" Jack responded, "but i'll talk to him about tonight, to make sure that he doesn't do anything he regrets if that'll make you feel better" "okay" Courtney said calmly, and I suppose he could have had a worse learning experience" she said with a smirk.