From Soccer to Sucker Pt.34

Chapter 44

Luckily for him lunch ended up being the worst part of his day as not a lot happened for the remainder of it. Still he spent a lot of his afternoon classes just trying to get over what had happened at lunch, constantly going over it in his head. Spending lunch with the girls and their questions had been embarrassing, but by far the thing which bothered him most was the run in with Tom and what he had said. It was hard to process just how far he had fallen in the eyes of his team, his ex friends. He couldn't help but wonder slightly how it had come to this, it had all happened so gradually that there was no clear point from where it had really gone wrong.

At least the thoughts of the blowjob he was going to get were starting to take over more and more as the end of the day and thus his blowjob drew nearer and nearer. Just thinking about it made him go mad with lust, making his cage all the harder to deal with. Having been pent up horny for way too long hadn't helped his case one bit and day dreaming about a pair of warm wet lips wrapping around his cock, the feeling of a tongue rather than a set of fingers, it only made his struggle with his cage harder. He needed relief so badly and maybe this would finally be the start of his road back to normalcy. Jake thought and hoped, a step closer to Valeria giving him back the freedom he needed not to have to be worried about hiding his secret as much. A blowjob was just a step up from the hand job, but still a step in the right direction. No matter what Jake was looking forward to the end of this embarrassing day for multiple reasons. After all he didn't need to worry so much when it was just him and Valeria which was a great relief from a day of nothing but worrying.

When his last class finally came to an end he got a text from Valeria telling him to go to her dorm straight away for their 'evening of fun' as she called it. Meeting with Valeria still got him kind of nervous, but above all he was really looking forward to it now that they were on great terms again, especially with the reward he was bound to receive. Even without it, getting cherished and toyed with by Valeria despite being embarrassing was also a lot better than spending his days alone in worry and self pity like he had done when he had refused to commit to their relationship by dressing up as Valeria's sissy maid. Upon his arrival at Valeria's dorm he barely got to finish his knock when the door flew open and she pulled him inside by his shirt only to close behind him and push him up against the door where she kissed him passionately. It caught Jake off guard, but like what was becoming pretty much a habit by now he quickly relaxed and let Valeria have her way with him. He might be physically stronger than her, but Valeria was manhandling him without issue.

"Fuck, skipping out on my lunch time orgasm, was a terrible idea. I'm so incredibly worked up, like you wouldn't believe it my sweet sissy princess, and you are going to fix that for me won't you? But all in due time of course. Right now it's high time to get you ready for tonight we're going to have so much fun and I guess I'll just have to wait a little bit longer no matter how it pains me not to use that delicious tongue of yours straight away. Spending time with my boyfriend Jake today was fun and all, but I can't wait to have my sissy girlfriend Jane back for some fun, so be a good boy and go get her will you? You can clean up in the bathroom, oh and babe, don't forget to wash your lingerie. You're staying the night so you'll need them clean for tomorrow." Valeria explained with a devilish grin as she finally released him from his spot up against the door only to pull him on his way to the bathroom and send him off with a firm pat on his ass and a chuckle. Jake couldn't help but blush brightly as he stepped inside, seeing his maid's outfit, lingerie and even the collar laying ready for him to put on. Just the thought of putting it back on made his blush grow more intense, but at the same time he needed to do this. He wasn't going to screw up his blowjob now.

It took Jake a while to get showered, dressed in his sissy maids uniform including the collar and heels only to wash the lingerie he had worn throughout today, which despite the frilly thong and sheer nylons was nothing compared to what he was wearing now. Then again it wasn't like he hadn't worn these things all weekend long so complaining about it now when he was so close to getting he blowjob would be stupid. Still back on his heels Jake couldn't help but doubly appreciate having worn sneakers all day long. At least those didn't make his feet sore, but then again this was only for an evening and his feet were finally well rested enough to handle these heels again for a little while. It was nothing to be proud of, but the fact that he didn't feel like he would be falling over or twisting an ankle also really helped. He was by no means perfect on heels, but good enough to handle even these tall ones after all his practice over the weekend.

When he stepped out of the bathroom he was pretty much instantly met with Valeria who had been waiting just outside with an ear to ear smile, clearly very eager to see her sissy Jane again. Jake couldn't help but blush over just how much better Valeria seemed to like him like this. It was nothing but embarrassing to him, yet at the same time it was kind of nice to see Valeria this excited, and that about him. He might be wearing different clothes and he might be called by a different name, but he was still pretty much the same person. Much to his worry however, her smile quickly turned into a light frown for some reason and he couldn't think of what reason that might be. It quickly became clear however when Valeria exclaimed. "Jane, where's your lipstick, and that pretty ponytail? I guess I haven't been very clear about the ponytail, but I was very clear about wanting my sweet sissy maid to have kissable lips at all times wasn't I?" Valeria scolded as Jake's jaw dropped in complete disbelief.

He had just gotten back in what was the most embarrassing outfit he had ever laid eyes on to please Valeria and still he got a scolding for missing a couple of embarrassing details. He should be mad about it, but after the weeks of careful manipulation by Valeria, getting him further and further under her thumb he just didn't have the confidence to get mad at someone, let alone Valeria herself. Instead he nearly automatically cast his eyes to the ground and squirmed a little feeling more worried and apologetic than mad. "I... I'm sorry Miss Valeria, I forgot. I promise it won't happen again." He said, hoping to avoid a punishment rather than starting an argument over it.

"Hmmm, okay, I forgive you, but just this once because you look so very cute in that dress. It better not happen again though or I won't be so forgiving. As my sissy maid it is your duty to look as pretty as possible for me at all times and doing your lips and hair are well within your capacities. I don't expect you to do the things you can't yet do, but I definitely expect you to do your best within your capacities Jane. Now off you go into the bathroom and don't come back out unless you're ready." Valeria smirked, squeezing his cheek for emphasis as she called him cute. Jake didn't know whether to feel relieved or upset about being called cute enough to be forgiven, but one thing was for certain he wasn't going to mess up again as he quickly minced his way back into the bathroom only to quickly brush his hair before putting it in a high ponytail with a pink satin ribbon, only to give his lips several coats of matching pink lipstick to really make them stand out with a thick luscious coat and look like every guy's wet dream. Facing his mirror image like that was mortifyingly embarrassing, especially with the act itself looking so feminine and sexy, but he did what he had to do.

When he minced out there, Valeria was all smiles again, and he couldn't help but feel completely over dressed. Valeria was still dressed in her more casual clothes she had worn to class, her makeup way less pronounced as well. Still at least Valeria looked happy now which meant that they could hopefully get to his blowjob, he needed it so very badly. "See, that's much better my dear sissy Jane, such kissable lips. Mmmm, it's so very hard to contain myself when looking at those, but I don't want to spoil them before we'll get to the fun part of our special evening. This milestone in our relationship, so let's go to my bed shall we? I'll do the rest of your makeup to make you look absolutely perfect." Valeria chuckled, having loved the flare of hope when she mentioned her bed only to be crushed with shame once more when she mentioned it was for the rest of his makeup. In either case she didn't give him much of a choice, simply clipping the leash to his collar and dragging him along to her bed while Jake did his best to mince in his rather crude way, the way she had taught him it was easiest to keep his balance in heels. It was just precious she thought.

It wasn't long before he was sitting on his knees next to Valeria's bed, right between her legs. He could quickly tell that she hadn't been lying about how turned on she was, able to smell her arousal very clearly which only caused another wave of discomfort down in his cage. Although he could see the lust and temptation in Valeria's eyes, she didn't proceed to push his head into her pussy like he had pretty much come to expect from her whenever she was horny. Instead she really did just focus on getting the rest of his makeup on, attacking his face with brushes instead. There was some blusher, not that he needed it, some eyeshadow, eyeliner and finally some mascara. It was rather embarrassing yet as with so many things he was getting used to it, besides the thought of Valeria's warm lips wrapped around his cock in just a few moments made it all so very worth it.

Thinking the moment he had been yearning for was very close now Jake couldn't help but be caught off guard when Valeria instead slid a soft pink satin blindfold over his eyes. "Mmm, there we go, all pretty and ready for your surprise. It's about time I got ready as well and I don't want you to peak so you'll get the full effect my sweet sissy. Now just crawl down here a little, yes, that's perfect. Now kneel, sit still and be quiet. I should warn you that I did order some take out, so if you hear the door don't panic you're well around the corner so no one should be able to see you unless you make too much noise and they insist on checking it out in which case that would be on you. If you would of course like to give the delivery guy a tip with those pretty lips of yours and show me one last time how it is you would like your cock to be sucked then you may of course tell me and I would be happy to oblige. So would you like to suck of the delivery driver my sweet sissy Jane?" Valeria asked teasingly as Jake's jaw dropped in shock.

"N... No Miss Valeria, I'll wait and be quiet." Jake stammered out. Sucking on a piece of silicone between a hot girl's legs was one thing, but sucking off another guy, there was no way in hell he would be doing that. He knew Valeria was just teasing him, or that that was most likely the case, but he couldn't help but wonder whether or not Valeria would seriously like him to do that or not. The thought alone made him shudder and made the idea of a delivery driver coming over while he was looking like this all the scarier. He was most definitely going to be as quiet as humanly possible to avoid such an encounter as much as possible.

"Alright then my sweet sissy Jane. In that case just wait here patiently and I'll be back as soon as I'm ready. Although a slight refresher course might have been nice." Valeria cooed with a giggle as she planted a kiss on his forehead and walked off, leaving Jake feeling like a complete sissy fool, vulnerable and all the more worried. Blinded as he was there was no way he would even be able to tell whether the delivery driver saw him or not. Hell it almost sounded like Valeria wanted him to suck that cock and with this blindfold on he would never know until it was to late and the cock was pressing right up against his lips. The thought alone made him shiver in disgust all over, but there was nothing he could do about it now, but trust that Valeria wouldn't actually push through on that front. Getting up and walking out as he was now was no option. Hell Valeria was in the bathroom with his clothes so he couldn't get to those either and even if he could, his bright pink collar was still locked on and nothing safe of a scarf would cover that up, so with that Jake was just left squirming on his stocking clad knees for what felt like an eternity, getting shook up with each new sound, like a shower turning on, turning off, the sound of thing coming down on the sink in her bathroom. Sound was all he had to go off of after all.

On many occasions Jake had thought about removing his blindfold to at least take a peek at what was happening around him, but once Valeria was done in the bathroom he heard her footsteps come towards him and was relieved he hadn't given in to that thought. After all he doubted that she would be pleased if she had found him sneaking a peek when she had explicitly told him not to. Just like that Jake was sitting there awkwardly on the floor, feeling the occasionally breeze of Valeria passing by him doing god knows what. On occasion he couldn't shake the feeling that she momentarily paused just to look at him, but there was no way for him to really tell. Eventually Valeria's footsteps became a lot easier to keep track of when she finally put on a pair of heels, apparently really dressing up for the occasion, which he really appreciated, but at the same time it was dragging on this sexual frustration for way longer which was horrible.

For as hard as it was to wait there blinded on his knees, it was nothing compared to the fear he felt when he heard a loud knock at the door only for Valeria's heels to rush of in that direction while he forced himself to not even squirm anymore. Any sound would be too much right now as he was terrified of someone seeing him like this. It was almost a relief when he heard the door close and only a single set of foot steps return, a single set of heels telling him that it had to be Valeria and just Valeria returning. "Dinner's ready Jane, but first it's time for your dessert. I just can't wait any longer, especially with that blindfold on. You just look so incredibly hot my sweet sissy." Valeria gushed as the heels stopped right in front of him, followed by some soft rustling of fabric quickly followed by a hand grabbing on to his ponytail and pulling him in closer. It was unfair, he had been waiting for this way longer than Valeria had, not having had relief for days yet here she was demanding another orgasm, before they even ate and get on with that blowjob he had been looking forward to for so very long. Nevertheless Jake offered up no resistance as he allowed himself to be pulled in closer until he could smell the arousal.

Much to his shock however it didn't smell like Valeria's pussy. It was definitely a pussy before him, but not Valeria's much to his shock and horror, of that much he was almost certain. Shocked and horrified Jake froze, stopping the steady progression to this pussy right in it's tracks. He could clearly smell it, feel the heat radiate off of it, but for the first time in a while he offered up some resistance to eating pussy. Someone was in the room with them, and he was terrified, the moment he had been dreading ever since his first panties had become a reality, someone now knew his secret and it was horrible. Still maybe with this dress, being called Jane, and the blindfold they couldn't actually recognise him. He had to believe so as it was the only hope he had left to cling on to as two sets of giggles at his reaction erupted above him. "See, I told you that anyone who has spent as much time between your legs as you claim wouldn't be fooled by getting another pussy presented to them." The other girl spoke sounding scarily familiar although he could not immediately envision a face to the voice. Still the idea that it was someone who he had definitely met before only made things scarier.

"Yeah, you're right, but it was still worth a try. I have to say that I'm quite proud of my pussy connoisseur. Knowing her Mistresses pussy like that, it definitely deserves a reward. Then again that's why we're here are we not? Now why don't you remove the sissy's blindfold, it has served its purpose." Valeria chuckled as Jake was panicking afraid that with the blindfold his last vestige of anonymity would be gone, although much to his horror it sounded like this girl, whoever she was was already in on it all. Not that that made him feel any more comfortable with the idea of his blindfold getting removed, although he guessed he would finally know who was standing before him so he could hopefully brace himself for the impact it would have on his college life. With his secret out he was totally screwed.

What he thought about it, like so often before didn't really matter in the eyes of Valeria or her guest for that matter as his blindfold was swiftly removed. Then again he guess he hadn't objected, but he hadn't gotten much time at all either. With his sight returned Jake was surprised and shocked to be staring right at a pussy with a neatly trimmed triangle of red pubes sitting right above it on pale white skin. It was nicely framed by a black lacy garter belt and sheer black stocking tops, a matching thong currently resting on her tall black stiletto heeled pump clad feet as one of Valeria's naturally tan hands held up the skirt of her little black dress from behind this girl's back. Just like it was one of Valeria's hands guiding his head towards this girl's pussy. Looking further up he could finally tell that this girl was the hot redhead from the clubs who Jake had fantasised about getting with going on accounts of how hot she was, and the stories he had heard from his friends after he had had to turn her down time and time again because of Valeria's rules preventing him from making a move on her. Right now on his knees in this over the top sissy maid's uniform, all dressed up and made up, it seemed silly and stupid that he had been afraid to do anything with her because of a stupid pair of plain white satin panties. Then again, he couldn't help but feel that if she had seen those then it would have been a disaster, that she would have mocked him, laughed at him, and potentially exposed his secret. Right now however, she was looking down on him with a lust filled smirk which had something sinister about it, although he guessed that was in part because of her pitch black lipstick and dark smoky eyes, contrasting heavily with her pale skin and fiery red hair.

Valeria for her part was looking over her shoulder with a similar smirk, only her lipstick was fiery red, contrasting with her tanner complexion and her raven black hair. She was wearing a sexy red dress and was just sliding back in a pair of tall red stiletto pumps which she had obviously taken off to sneak for the surprise effect, fooling his senses. It was very clear from the way their outfits and makeup were coordinated that this was a very planned event and Jake had no idea how to feel about it. Here he was in front of two of the hottest girls he knew, who were fixing him with lust filled eyes, dressed and made up as sexily as they could, a wet dream come true and yet he felt more vulnerable and embarrassed than ever before. He couldn't believe this was happening, that Valeria had let someone in on his secret, he wanted to run, to hide, but at this point that would hardly matter anymore. "Hmmm, you are right, he does make a very cute sissy. I would have never expected so when I first saw him, and I definitely didn't expect to find so big a sissy, but he's adorable. To think I thought of him as a relatively boring macho guy who's sexual horizon's I wanted to expand a little." The redhead giggled while Jake continued to blush.

"Hmmm, well he was a boring macho and an asshole at some point, but I think this sweet sissy was hiding inside all along. I'm sure there are plenty of sexual horizon's to expand however he's been on a strict diet of handjobs for as long as we've been together, but tonight's a big night for my sweet Jane. She's been a very good sissy which is why she has earned herself a blowjob and from what I've picked up from some proud banter among the guys you are quite the expert on that. I only want the best for my sissy and well I've never sucked a cock before. While Jane gave me a nice demonstration of what she likes on my strapon last night I doubt I'd be close to half as good as you are. If you're still up for it that is. I also know that she thinks you're incredibly hot, in fact I think she might have actually cheated on me when you came onto her, the panties she was wearing at that time were the only thing keeping her from doing so I think. She's not the only one to think you're incredibly hot though, I've never been with a woman, let alone in a threesome so you'll definitely do some horizon expansion around here." Valeria cooed in the redhead's ear, before planting a kiss at the side of her neck.

Jake for his part was struggling big time down on his knees before them. Seeing Valeria and this redhead in such an embrace, was incredibly hot making the situation in his cage all the more dire. Not only that, he couldn't help but feel incredibly embarrassed as well hearing them talk about him like that. It was mortifying, but there was little to be done about it. He was surprised that it wasn't his charm this redhead had fallen for, but a desire to expand his horizon's whatever that meant. It actually came as a bit of a shock to him, despite not having put that charm to work in what felt like an eternity by now, not that it mattered at this moment. He definitely would never be able to look at this girl the same way ever again, especially not since Valeria had basically heaped on even more embarrassing aspects of his situation with her explanation. On top of that all he was stuck with very mixed feelings towards the blowjob he was going to get. On one hand he had fantasized about getting a blowjob from this girl ever since hearing how amazing she was, on the other hand he couldn't help but feel like it was unfair. After all this talk of stepping up their relationship, Valeria wasn't going to be the one to suck him off after all, and that after he had gone out of his way to suck on her strapon supposedly to show her, only for it to have been all for nothing.

"Mmmm, of course I am up for it. I'm always up for some fun and I love expanding my own horizon's as well, I don't think I've ever been in a threesome quite like this before and the two of you seem like a very fun and hot couple." The redhead exclaimed as she threw here head back with a moan, enjoying the gentle nuzzling of her neck before turning her attention down to look right into Jake's embarrassed eyes. "Oh and Jane is it? I don't think we've ever had the pleasure of exchanging names. I'm Jessica, although I go by a lot of names, some call me hot slut, other's crazy fun nympho, still other's like to call me their bitch, but I love switching things up and seeing you collared and on your knees is such a cute sight to behold. It definitely awakens my dominant side. You can call me Miss J." Jessica said while gently stroking one of her fingers underneath Jake's chin as his blush deepened.

"Keep that in mind Jane, and don't forget, that's Miss J regardless of the situation from now on. In any case, I think it's time you showed Miss J what a great pussy licker your are. Besides, it's impolite not to give her a welcomes kiss, you wouldn't want her to have to kiss that bottom of your with the palm of her hand several times over now would you?" Valeria grinned as she turned her attention back from Jessica's neck to Jake on his knees only to push the back of his head a little harder towards Jessica's pussy. She just loved the shame in his eyes, spiked with a clear hint of lust as well. She just loved the effects she was having on, even that he was definitely liking part of this as despite loving his shame she actually wanted him to enjoy this as much as possible. It made her feel better about liking this so much herself as she did know what she was doing was wrong on way too many levels and that doing this for the greater good was partially a lie she was telling herself. Jake couldn't be anymore humbled, but she couldn't give up her sissy boyfriend.

Down on his knees with both hot girls looking down on him expectantly Jake simply stopped offering up resistance which instantly sent him forward with his face in Jessica's pussy. Jake didn't hesitate to start licking like he had done so many times before for Valeria. It was almost a habit whenever he came in contact with a pussy by now. He couldn't really remember the last time he touched a pussy in a sexual manner with anything other than his tongue. After all this talk of cheating and how he wasn't supposed to cheat he couldn't really believe that it was Valeria who was pressing his face in the pussy of another girl, but here he was. It felt degrading if anything, but he still did his best to please Jessica to the best of his abilities, and despite the fact that Valeria seemed to be enjoying it the most he still thought it was incredibly hot to see them make out like that. The instant gasp Jessica let out as soon as he had gotten to work with his tongue, sent a surge of pleasure to his caged member which was trying ever so hard to escape from its prison. It wouldn't be too long now, in fact that was why Jessica was here even if given the state of things it looked like she was more here for Valeria than for him. It would still be incredibly hot to have her suck his cock while Valeria watched though. This was a threesome that would have never happened in his wildest dreams and yet now, thanks to Miss Valeria he was living it, not in the way he had hoped, but still.

"Mmmm fuck yes, you weren't kidding, this is amazing, and you say all you have to do is snap your fingers to get to enjoy this? Lucky girl!" Jessica moaned as Valeria kept on nuzzling her neck lovingly, gently petting Jake's head now that he had gotten started. It felt good to feel her loving touch, yet degrading at the same time, and that wasn't even talking about the fact that Jessica wasn't even directly complementing him, but rather turning herself to Valeria with her compliments. Still it felt great to hear that this obviously rather experienced and hot girl thought he was great. It filled him with a weird pride, yet imagining that one of his friends, or rather ex friends might have fucked this very pussy rather recently added a whole new layer of shame to it as well. He didn't even know why that thought had so suddenly occurred to him, but it did and it was mortifying. Not something he had ever minded before despite being with plenty of girls one of his buddies had already been with and not objecting to eating their pussies as a means of foreplay, but then again he would get to enjoy them later on which wasn't the case here and now. Given his recent sexual history or rather lack there of, it hit very differently though.

"Well you're most definitely welcome to lend him anytime you'd like, I'm sure I'll figure out a way for you to repay me somehow." Valeria grinned as she took the hand that was petting Jake's head up to Jessica's chin only to turn it back a little further while she reached forwards so she could kiss the other girl rather than to keep nuzzling her neck. Jake in the meantime couldn't believe that Valeria had just given someone permission to use his tongue whenever they pleased. Worse, they prostituted his tongue for whatever favour she would think of asking as payment. Yet despite all that he kept on looking up with lust and fascination as they made out, pleased that Valeria hadn't used the hand holding Jessica's skirt to direct her chin. After all if that had dropped the show would have been over for him. Down on his knees continuing to give it his all he couldn't help but notice how Valeria and Jessica seemed to make out more like equals than anything, while with him Valeria always very clearly took charge. Then again given that he was collared, dressed like a sissy, in chastity and down on his knees was way more telling than the way they kissed, he thought as his faced turned red yet again.