Ballers

Ballers (Part 7): Dreams do come true

Yan could not stop admiring Cassie. She was so happy that her dreams of seeing Cass dolled up had gone from her shower fantasy to reality in the space of a couple of hours. She could not believe how compliant Cass had been. It had helped that they had been able to have open conversation earlier about what their feelings were, not just to each other but what they both enjoyed.
Standing there, holding Cass by his cute ass and feeling his lipstick as they kissed was definitely turning them both on. Cass felt his excitement was not as physically obvious to Yan due to the layer of petticoat under the dress. But there were still some voices of his old self, shouting at him to be on the attack and show Yan who the boss was. And at that point in time, looking like a girl and being kissed like one, he mustered the courage and said, " You have had fun doing this to me, now it's my turn to do something to you , something that we haven't done yet as lovers!"  Yan was surprised Cass had found his voice and was reminded she might not get all she wanted even when it seemed to be moving along at her tempo. " Oh yeah, and what's that, gawwwwgeous?" She said, trying to emphasise the last word to make him aware of her adulation.
Cass said,"Ever since we have started seeing each other, things have been difficult because of my back conditions and it felt like we never got a chance to have sex like I have always done - with me on top and fucking you. I want to make you experience what pleasure I can give you with that." Yan was thinking quickly if she ought to push back and "block the shot" like she would do in basketball and find a reason not to let Cass have a go  but felt that would be cruel. She had discovered from earlier relationships that traditional PIV sex was never as enjoyable, and she knew she enjoyed being on top much more, with other forms of touching and rubbing, and visually seeing her partner under her control much more appealing. She had ofcourse enjoyed when she had ridden his cock, but clearly Cass's ego was wanting to get on top and fuck her in a more traditional way. She decided she had to let this play evolve and see if there was a better time to control the narrative.  She said in a very flirty tone, " Ok, I am intrigued as to what you mean. Have you got a few tricks you haven't shown me yet, lover boy?" She said as she kissed him again. Cass liked the response but knew this meant he had to now back his words up. "Come on, let's get in bed and let me show you". Yan followed, imagining was might be in store but she did find it hard to take her eyes off Cassies breathtaking beauty and the feminine curves the dress was accentuating.
Cass got Yan to lay on the bed and he laid beside and started kissing her. He pulled her hoodie over and was admiring her exposed breasts and started suckling and tweaking her nipples. Yan was enjoying it and Cass was deftly also pulling her sweat pants off to reveal her panties. Yan knew she was not comfortable with not leading, but she needed Cass to feel empowered again. Strangely he had not remembered or bothered to take his own dress off so Yan certainly felt like she was being seduced by a pretty girl. Cass was good at playing with her through her panties and even went down between her legs, spread them and started licking and kissing and running his tongue on her sensitive, throbbing clit. "Mmmmm Cassie you have a gift with your tongue", she moaned. She decided to feel Cass by reaching under his dress, and pulling his shorts down to let his growing cock rub against the silk of the undergarment. She knew Cass would like that. And this was perhaps why he may have decided to even keep the dress on, so Yan decided not to comment about not being able to see his erection. "Mmm just feeling it so excited is turning me on", she said. Cass felt a return to familiar sexual positions and he said he was going to show her how excited he was and climbed over her and started to pin her down, pressing his cock between Yan's thighs. He could feel his throbbing dick  sliding into her wet and ready pussy. But Cass did find it hard to thrust, keep his body bent over Yan and reach down to kiss her or squeeze her breasts. Yan was reaching around and squeezing his chunky ass and let Cass hold her down. Cass was breaking into a sweat and felt he was not going to be able to keep on much longer with this exertion and decided to take a little break. Yan asked him to lie down on him if he wanted a break for a few seconds and kissed him again, saying how gorgeous he looked. "Oh you look so pretty Cassie",she whispered. She was desperate to feel and nibble his nipples, but it was hidden under his dress and the t-shirt he had on, and she was not wanting to give him any excuse to take his dress off either, so she decided to wait until a bit later on. Whether it was the reminder of his feminine look, or the hormones or his lack of exercise having sex like this in several months, Cass felt a pressure to perform, which was not helping him keep his usual strong erection. He could feel he was slipping out of her. " Sorry, I don't know what's the matter" he apologised. "oh don't be silly, you are doing great. I am enjoying it" Yan lied. She was secretly pleased the traditional or PIV sex, was not going well. It was not particularly that his cock was hurting her, but she just disliked not being in control. "Maybe you are just tired, do you just want to cuddle like always and just get some sleep?" she asked him, as Cass rolled off her to the side. Cass was clearly feeling a little annoyed he had not been able to perform like he had bragged about, a few minutes ago. Yan stroked his hair to one side, resting her arms around his now slender waist. Cass didn't want to concede defeat so easily. "I am just finding my shoulders and elbows are not as strong, and I am feeling a little dehydrated as well...I think ..". He was uncertain what was happening. "Shall we take it slow and maybe go back to some passion that we know works?" She winked as Cass turned to look at her. And before he could say anything, she jumped up and said, "Relax and think about it, I am going to get you a glass of your favourite iced tea I had made earlier."
Cass was definitely turned on, he just seemed surprised at having his sexual competence under scrutiny. Yan was definitely making no fuss over his lack of vigor. He did hear her rattle the draws in her bedroom, before hearing the clink of glasses from the kitchen. Yes, maybe he just needed to rehydrate and give it another ago.
Yan walked in with a tall glass of the iced spearmint and licorice lemon tea. It was a combination she had thought up as they were both fans of the flavours. "Cheers to a few days of PJs and pretty dresses?" Yan clinked his glass laughing. Cass drank nearly half his glass in one go.  Yan put something under her pillow before getting in bed close to Cass, and sipped her drink while the free arm snaked back around his waist. "You ok?" she asked.
Cass said,"Can we start again, I want to know if anything has changed for my own peace of mind". Yan realised there was more at stake than just her preference for their intimacy. "Ofcourse, hey, listen there is no pressure. I still love you and I have been looking forward to enjoying the holidays with you. And I want you to enjoy it too". Cass reached over to kiss her and they were again back to deep french kisses. Cass pulled her close and was kissing and suckling her nipples while playing inside her panties with his deft fingers. Yan moaned and opened her legs, inviting Cass to get between and he duly obliged positioning himself again between her thighs. He gave gentle kisses all up her thighs and when he reached her lips, ran his tongue over her labia and clit, making her quiver and moan. She could feel his cock getting hard and brushing against her leg, even through the dress. She lay back and opened her legs more to give Cass and his tongue easier access. She could see his rounded and cute bum as he bent down to finger and lick her in sync. "Oh my god, you are so good at this" she said, holding his gorgeous long hair and head as he worshipped her wet pussy. Cass decided he was excited enough to give Yan an even bigger surprise than his oral technique. He again lifted his dress to position himself against her opening and thrust forward, hearing her moan and pull him in closer. Yan did feel Cass was bigger and going deeper into her this time. She reached out to squeeze his ass again and her fingers again brushed against the his inner ass crack. She could see Cass's eyes open wide and smiling as he kept thrusting. He was resting his hands against the pillow to support him. He was excited, he was throbbing and yet, his elbows were starting to hurt and it felt like he was not as hard. He felt the need to rest again for a little while, as Yan pulled him closer to kiss him. She could see he was tiring and wanted to just hold him for a few minutes before he recovered . She was no longer feeling him deep in her, but he was softening. She decided it was time to act before Cass started doubting himself.  "Hey, why are you the one to have all this free work out. Let me have a go, please ?" She asked flirtatiously and rolled them both over, so she was now on top. Cass had his arms on her shoulders, grateful for the support and the rest to his elbows. He was still inside Yan, but had started losing the hardness. Yan slowly started riding and his stirrings began again. "just lay back and enjoy Cassie", she whispered as she now straddled him and started slowly moving back and forth to get him excited again. "Can I have a feel under your dress please darling?' she said and unzipped his dress and pulled the sleeves down. "Oh look, you have a t-shirt underneath. Pretty girls have sexy bras!" she said teasing him, and pulled his t-shirt off over his head too so his chest was now exposed. Yan peered at Cass and noticed he was getting flesh around his nipples. She realised he was always in a top or shirt at home and it had been a while since they spooned naked, so she had not even noticed. There was no mistaking, but there were little buds of breast tissue. She did not want to say anything in case Cass was scared by it. She kept riding him and was pleased he was starting to get hard again. She then reached down and gently suckled his nipples, and a moan escaped his lips. "mmmmm" he said holding her face. She then gave it a nibble while tweaking the other with her finger. "Unnnnnggghhh aaaahh Yannn", he was definitely feeling very sensitive but didn't want her to stop either. She could feel him throb inside her as she kept riding him. She was definitely more comfortable in this position and clearly Cass was enjoying it as well. She was starting to up the tempo and could feel her insides building up to a climax. The lower half of his dress was still  on and it was rubbing against Yan's clit so she was enjoying the feeling. "Are you getting close?" Cass whispered. Yan was indeed, but realised she needed to be mindful of what Cass wanted.  " Oh yes, are you ?" she asked.
" Oh I am excited, but not sure I can come yet," Cass said. "Just feels a bit different, not sure what", he added.  "ok, let me slow down and let's keep playing. We have all night !", Yan added helpfully. Cass was excited, but just couldn't understand why that didn't translate into getting to climax.  Yan's suggestion to keep playing was appealing to him. And when Yan reached under the pillow,  Cass knew what might be in store. What was different this time though, which intrigued Cass and made his eyes open wide, was the vibrator was a curved dildo attached to a harness. The vibrator was purple , veined and had a clit bumper at the harness end of the strap on.  Yan had clearly been hiding this accessory before.
"Just close your eyes and lay comfortable Cassie" Yan told him. He could hear the buzzing and drew a sharp breath as he felt Yan apply the vibrations on his cock, which yet again duly complied and started growing hard. Yan was a wizard with it, running the vibrations all over the shaft and pausing to slow at the sensitive tip which got Cass to moan loudly and hold Yan's free hand that was tweaking his nipples at the same time. Cass realised the vibration speed slowed down and  wondered what Yan was up to and opened his eyes, she was looking at him with a big smile, and was enjoying running the vibrator now to the bottom of his shaft and moving slowly under his balls and massaging his perineum. Cass remembered it was what had made him explode on his first night at this house. This time he was still highly excited but appeared to be a little bit more in control. Perhaps it's the speed, he thought .
Yan moved it further back and he could now feel the gentle vibrations at the entrance to his rectum. A part of him wanted her to stop so he could go back to being on top of her, but a bigger part in control of his brain made him open his legs and spread himself involuntarily. He opened his eyes and saw Yan stick two fingers into her wet pussy, while positioning the tip of the vibrator at his entrance. She then swapped it around so her wet finger was pushing into his hole slowly but firmly, while at the same time squirting some lube onto the shaft of the vibrator. Cass was finding the sensations incredible, and he was still in admiration of how adept Yan was, even with sex toys and playing with him. He was laying propped against the pillow, with his dress around his open thighs and his little erect nipples poking proudly . As he closed his eyes again, he felt Yan gently withdraw her fingers, squirt a bit more lube and felt the cool and sticky lubricated finger probing into him again, loosening him up. Just as he relaxed, the finger pushed past his tight sphincter and the familiar and beautiful sensations of Yan's finger massaging his prostate made him moan and bite his lips. Yan moved closer and suckled his nipples before opening his mouth and french kissing with her tongue all over tongue. "Are you enjoying this Cassie?", she whispered. Cass had a dreamy look and could only nod and smile. She drew her finger back out and said "Just move your cute ass on to this pillow, it will support your back". Cass wriggled his ass to get himself propped on the pillow. He was now flatter with his head back on the pillow but his dress and his thighs were exposed, for easier access to Yan. She asked his to close his eyes again, and when he did, he could hear the familiar buzzing again. He kind of knew what to expect now as he gripped the sides of his pillow beside him with his hand nervously. The buzzing stopped, but he felt the shaft press against his hole again, this time he felt more force against it, and he realised the vibrator was now secured into the strap harness that Yan was now wearing! His eyes again opened wide as he looked at Yan kneeling between his thighs, looking down at him with a big smile. Yan pressed further and was soon through his outer ring, pressing against the inner sphincter. "Argghh, mmm oh gosh", Cass was definitely moaning in a higher pitch. Yan was now positioned perfectly to push her way through. Cass looked up at her with a pleading look, "Just relax darling, I will be gentle", Yan said as she pushed further in. Her weight and her soothing voice relaxed him enough to take it all the way in and he could feel the tip of the dildo pressing against his prostate and starting to rub as Yan rocked back and forth slowly. "mmmmm oh that feels good Cassie" Yan said. Cass couldn't speak and just  moaned in reply. Cass made eye contact with Yan, who was beaming and then reached down to flick a switch, and the vibrator started buzzing again - only this time, a lot of it was inside him. The clit bump was vibrating against Yan's clit and she was letting out little yelps as well. Cass couldn't help let out a little scream as Yan pressed further into him. They were both throbbing. Yan bent down to kiss him, and neck him as the vibrations were making her climax violently. As her juices squirted, she could feel squirts of clear liquid ejecting from Cass's cock making a sticky mess between her belly and Cass's dress. Cass opened his eyes ,but was still shaking and gripping Yan's shoulder tight as he was still continuing to come.
It took a few minutes before their breath came back and Yan was giving Cass several gentle kisses, realising for the first time Cass had his legs wrapped around her waist.
"Oh my gawwwwd, that was incredible" Cass was the first to speak up.  Yan had been a little worried Cass's ego might have been bruised, but clearly the enjoyment was palpable from his tone and facial expression. Yan looked at him and said "YOU were incredible. You look so pretty... I hope I didn't hurt you too much?" . Cass had a beaming smile as well now. As Yan slowly wriggled herself off him, Cass let out a little sharp intake of breath as her strapon popped out. Yan took her harness off and laid beside him holding his hand before rolling to her side and laying her hand against his chest, clearly feeling his breast bumps under her arm. Cass rolled on his side so she was now spooning him and her hands settled on his lower nipples for support. He let out a big happy sigh... He had not managed to achieve what he may have wanted to do, but as always Yan had discovered a level that he didn't know existed. 
They both drifted off to sleep with Cass comfortable in Yan's embrace. Yan's face was pressed against Cass's neck and her legs wrapped over his thighs, with one of her hands firmly clasping his breasts. She smiled, realising he had not even wanted to take the dress off before drifting off. Yan couldn't believe her luck at the turn of events this evening- was her fairy godmother passing by to grant her wishes?