His sissy training (closed)

[sissykaitlin]

Kelley nodded his head as Lindsay spoke to him, listening, but not quite listening quite close enough to what she has been saying. When Lindsay took her hand off of his cock and instructed Jena to the back Kelley was surprised. Kelley made eye contact with Lindsay as Jena unbuttons her shirt to reveal her breasts and pulls her cock out.

Kelley clearly hears Lindsay telling him what Jena likes, and nods, realizing just what he has gotten himself into. Reaching over to Jena's lap Kelley makes eyes with her and is relieved to see her nod her encouragement as his hand wraps around her cock. Kelley bites his lip as he begins to slowly stroke her cock surprised to find how much he enjoys feeling her throbbing in his hand.

The more comfortable Kelley gets with handling Jena's cock the bolder he gets--his fingers moving down to play with her balls and his eyes not breaking from hers. Kelley leans forward into Jena as she moans louder. His lips wrap around Jena's breasts and he hears her moan loudly. Making eye contact with Lindsay again Kelley smiles, shyly, and allows his spit to fall onto Lindsay's cock. "Mmm, this is so much better when you're a little wet, Jena." Kelley laughs and with his free hand pinches her nipples, completely oblivious to the passing traffic.

 

[SRP_lover19]

Lindsay didn't need to look back to know that Jena was being taken care of by Kelley. Jena is moaning and arching her back to Kelley's touch and she barely gets out "Am I doing well at pleasing you?" She started to rub his cock faster and harder trying to get him to moan out as well. She had always made sure her partner was being satisfied as well as her own cock. "Kelley Jena loves it when her partner and she cums at the same moment so if you are holding yourself back to make sure she cums first you won't cum at all because she has been trained to cum only when her partner has." They both hear from the front seat. Jena could tell that Lindsay was getting horny watching the two go at it in the back. Jena firmed up her grip and with her other hand she drove her hand under his balls and to his bottom. She lightly teased his ass hole before she slowly sunk a finger tip into it. Jena grinned a bit before she slowly began to fuck his ass with her finger tip. She didn't know if he like that at all but she knew he had to get used to it and love it because there would eventually be bigger things inserted into it.

 

[sissykaitlin]

Feeling Jena starting to pump on his cock faster Kelley's had dropped back and he let out a loud moan that surprised him--but he wasn't embarrassed as Jena's moans & gasps were nearly continuous. Kelley hears Lindsay from the front seat and acknowledges what she has informed him of. Kelley almost jumped out of his seat as Jena's hand reached down to play with his bottom. At first he arched uncomfortably but as she began to insert her finger into his ass Kelley let out a long low moan. "Mmmm, Jena how did you know that I would like that?" Kelley leaned forward and kissed Jena squarely on her lips his hand reaching up behind her, tugging on her hair, as he kissed her. His tongue wrapping with hers as he lifted his hips encouraging her finger deeper into his ass. Pulling his lips from hers Kelley blushed and asked what he had been curious about. "Jena, can I suck on your cock?"

Kelley looked to the mirror and caught Lindsay's eyes. Knowing that he was close to cumming Kelley wanted to taste Jena and give a Lindsay a little show before they both came.

 

[SRP_lover19]

Jena looked and him before saying "I wish we could do more than this right now but yes you can." She guided his head down to her cock and helped position his body so that she still had access to his cock. She couldn't wait to feel his lips on her cock and she gave Lindsay a nod. "If we give Lindsay a good show she may let us fuck each other later when we get home if you are into that." She removed her finger from his hole and snakes her hand down the back of his pants this time she slowly slides her whole finger into his hole as she kept stroking him. Her nipples where as hard as pebbles and the air that was being blown around by the air conditioner was making them tingle with pleasure. Jena couldn't wait till they got home because then they all could have some real fun.

 

[sissykaitlin]

Kelley smiled and hesitated--his hand firmly wrapped around Jena's cock as he began to lower his head. He was nervous and uncertain as to his ability to suck on a cock--but he had been fantasizing about it for months. But of course, he had never expected to be so bold with Lindsay & Jena.

Kelley moaned around Jena's cock as she stuck her finger deep into his hole. Kelley's free hand played with Jena's nipples as he sucked on her cock. He was surprised to find that with more practice he was able to take her cock deeper and deeper into his mouth. Kelley could feel his cum building as Jena continued to play with him and paused sucking on her cock to gently suck and tease her balls--his tongue darting out to tease them before going back to sucking on her.

Lifting his head up Kelley kissed Jena passionately and looked forward to Lindsay, again. His hand wrapped around Jena's cock and he lifted his hips knowing that he was soon to be reaching his orgasm.

 

[SRP_lover19]

Jena could tell by how Kelley was acting that he was either close to cuming or his cock was about to erupt. She continued to finger his hole as she stroked him and he stroked her. "I'm about to cum please cum with me!" She squeeled and moaned out feeling her balls grow tighter. She soon felt herself on the edge of cumming and she held herself there waiting for him tocum.

Lindsay couldn't help but to pull her very large G cup breast and start to play with them. She couldn't stand that she wasn't the one that they were pleasuring. She could feel her panties and dress begin to soak through as their act went on. If she knew that she could focus Lindsay would have started to play with herself by now. "I hope you are read to cuddle her afterwards because she gets clingy after she cums." She coos as she speaks.

 

[sissykaitlin]

Kelley let out a low moan as Jena told him that she was close to cumming. Kelley looked at her cock and was amazed at the amount of precum that was dripping from her. His finger traced over the head of her cock and he then lifted to his lips, tasting her. Kelley looked forward catching Lindsay's eye and sensing her approval of his actions, thus far. He could see through the mirror her hand moving to her breast and playing with them. Kelley smiled, remembering what Lindsay had said about Jena and reached over squeezing her breasts--playing with her nipples as he approached his orgasm.

Just as Lindsay began to tell him about what Jena liked Kelley lifted his hips and bucked as thick ropes of cum splashed all over his chest and stomach- dripping down as he unwound from his orgasm. He was amazed just how hard he came. His eyes barely remaining open as he felt his hearth thudding and his legs twitching. Collecting himself Kelley looked up to Lindsay and smiled bashfully.

 

[SRP_lover19]

Jena seen that Kelley had started to cum and she positioned herself to cum on his stomach as well. She had shot a hug load all over him and when she was sure she had stopped she unbuckled herself and slide over into the middle and used the seat belt there. she removed her clothes and cuddle against him as his body spasmed from his money shot. Lindsay could see that everything had calmed down in the back so she stopped massaging her breast and focused on the driving. She looked back to see Kelley smile and she grinned back and she also noticed that Jena had slid his pant down to his ankles. Jena also wrapped her legs around his. Lindsay couldn't help but to smile looking back seeing both of them extremely spent together.

 

[sissykaitlin]

Kelley sighed and was surprised as Jena cuddled next to him--taking the empty seat and curling into his lap. He put his hand on her back and slowly began tracing circles. Kelley was surprised that his pants were down around his ankles but wasn't upset about it knowing that his and Jena's cum was now drying on his stomach. He traced a finger over the mixture and caught Lindsay's eye as he lifted his finger to his mouth and sucked on it--tasting their mixture.

Kelley closed his eyes, relaxed and feeling comfortable with his soon to be new roommates. Smiling to himself he started to hum and kept his hand on Jena's back.

 

[SRP_lover19]

They soon got home and Lindsay turn to the two and said "you two are to clean the inside of my car because I don't know if you got any cum anywhere else but on you two. Jena get him his latex uniform." She grabbed his cock squeezing hard enough that he knew she ment business and said "you will be silky smoth while you are here no hair but on your head. I will order you some panties today but for now you are to wear a latex pair." She let go and got out of the car.

Jena looked over and said "shave first then we will get your uniform on you and clean the inside of the car. There is only lady razors so use those." She got out of the car and got her frilly French maid uniform on and then she dug out his latex version without anything covering his back but two strings that tied it together. She hurried to the bathroom making sure she got his black bikini cut latex panties. "You ready?" She asked as she entered.

 

[sissykaitlin]

Kelley smiled at Jena as Lindsay instructed them to clean the inside of her car. Kelley groaned softly as Lindsay squeezed his cock. Kelley looked outside of the car and saw the latex outfit hanging in the garage--against the wall. "It's like you two were expecting me to come home with you!" Kelley blushed embarrassed that the effect that they were having upon him. Kelley helped Jena clean the car--finding little cum as he was certain every last drop had landed on his own stomach.

Kelley took the razor from Jena and found a mirror. He shaved his face clean before focusing in on his torso and legs until he was smooth. It took a little over a half an hour to ensure that he was completely clean and each time he looked up Jena was not too far away. "Would you mind helping me with my backside, Jena?" Kelley blushed and held out the razor.

Kelley eyed the latex outfit and could feel himself getting excited at the prospect of wearing this for Lindsay & Jena.

 

[SRP_lover19]

Jena gave Kelley a smile before she said "yes I will." She took the shaving cream and sprayed some out in her hand then said "I'm going to shave everything back here to make sure you got it all but fist lean forward so I can get your back first." She gently pushed on his back as he pressed her cock in between his cheeks. even though there was two thin pieces of fabric 'her panties and her slutty uniform, she couldn't help but tomoan out a bit when her cock touched his ass. After she spreads the shaving cream on his back she grasped on hip with her free hand pulling him in to her thus pressing her cock into him more.

Lindsay walked in and seen the two working together and said "that's what I love to see my two women working together. Kelley I want you to meet me in my room we will have to talk a little ." She. walks beside the two and reaches her hand out and plays with their balls a bit. "And don't forget Kelley my dear make sure you're in your uniform there." She said as she let go and turned to walk out. She got into her new full lenght gown and matching panties. She sat at her computer which hid everything so he couldn't see and she waited.

 

[sissykaitlin]

Kelley blushed as he felt Jena's cock press between his cheeks, and arched his back. He was surprised about how much he enjoyed the thrill that ran down his spine. Kelley leaned back into Jena's body allowing himself to get relatively comfortable and hoping to give her the best angle to shave him from.

Kelley looked over his shoulder as Lindsay came in and nearly jumped as she told him to visit her. Kelley waited patiently as Jena finished cleaning him up. Bending at the appropriate times to give her access to his deepest crevices. He moaned softly as he felt her hand on his ass--spreading his cheeks as she cleaned his naughtiest places.

Upon finishing Kelley ran his hands down his thighs and spun around looking at himself in the mirror. "Oh, Jena! I look and feel great!" Kelley leaned forward and planted a wet kiss on Jena's lips before getting embarrassed and pulling away. Kelley looked around the garage and found the latex uniform that hung from the coat hanger. Lifting it up Kelley eyed it skeptically. "Jena, uhm, do you think you could help me with this so that I am ready to see Lindsay?"

 

[SRP_lover19]

Jena helped him get into the latex thigh high stocking and the almost shoulder length latex gloves . She waited for him to pull up the panties and then she helped him tie the strings of the maids dress. Once done Jena gives him a pat on the bottom before saying "you better hurry to the mistress' room or she may give you a spanking."

Lindsay heard Kelley enter the room and she said "sit on the edge of the bed I want to order you some panties and I need your measurements." She did knoq if he could see what she was wearing but he was soon. She walk out from behind the desk and over to her dresser giving him another look at her white gown she showed him earlier. She grabbed the measuring tape and said "up now I have a site that makes custom panties and they will need your measurements ." She waited for him to get up so she could take his proper measurements.

 

[sissykaitlin]

Kelley walked into the house hesitantly--still not having seen himself in a mirror. As he entered the home he marveled at the openness-- with lots of windows and natural light. Kelley smiled as the hallway in from the garage was covered completely in mirrors. He spun admiring himself as he walked. He liked how this outfit fit him--though, it was a little snug, in the places that mattered-- and couldn't believe that he was here, and that a woman was waiting upon him.

Kelley sat on the edge of the bed with his knees. He waited patiently as Lindsay began measuring him. Kelley gasped upon seeing her white gown. "Oh, Ms. That gown. It looks fabulous on you..." Kelley blushed and went quiet again. Standing up again Kelley couldn't help but wish that his firm cock would go down but there didn't seem to be any chance. Here he stood dressed in a latex maid's outfit with a woman parading around him taking measurements! He stood as Lindsay instructed--patiently, letting her get the measurements that she desired. What heaven!

 

[SRP_lover19]

Once Lindsay had gotten all the measurements she needed wrote down she pushes Kelley down on the bed and crawls on top of him. She firmly sat down on top of his cock and asked "even though your a lowly maid you want to stick your cock in your mistress don't you?" She begins to bounce lightly up and down on his pelvis waiting for her answer. She had been horny after watching Jena and Kelley play with each other. She wanted cock in her badly but she wasn't going to beg for it. With what she had planned for him he was going to be the one that begs for her pussy.

 

[sissykaitlin]

"Yes, Mistress. I do." Kelley's hips began to lift against Lindsay but he hesitated not wanting to upset her. Kelley moaned quietly as he waited to see what Lindsay had planned. "Mmm, Ms, I'm aching since you told me to dress up for you!" Kelley looked down and couldn't help but blush knowing that his cock was firm and twitching underneath Lindsay. Leaning forward Kelley began to press his lips--ready to kiss Lindsay but still not certain what was appropriate for him to take the initiative on.

Groaning loudly Kelley met Lindsay's eye and began to tell her how much he was ready for her--practically begging as she rhythmically bounced on top of his cock.

 

[SRP_lover19]

Lindsay knew he was wanting her badly as much as she wanted him but she still needed him to beg for it and she began to grind herself on his cock. "I think that you really don't want your mistress' pussy very much I think I may have to get the other maid to do it for me then." She teasingly moaned out as she pressed harder and harder on to his cock. "Your panties must be getting filled with your honey by now." She whispered into Kelley'ss ear getting close enough her lip barely grazes the ear.

 

[sissykaitlin]

Kelley moans and begs Lindsay for more as she leans forward to whisper in his ear. "Mmm, Ms. Lindsay. my panties are definitely filled!" Kelley can feel his panties clinging to him and knows that he is so close but refuses to satisfy himself without first satisfying Lindsay. Kelley's hands trace over Lindsay's stomach and back to her ass, pulling her against him as he attempts to fill her.

 

[SRP_lover19]

Lindsay could tell that he would do anything at this point to satisfy his cock and she laid beside him saying "lets watch some live naughty entertainment. Jena come in I know you're waiting outside the door so come in and show us the trick you can do." Lindsay got naked as she waited for Jena to get her office chair set up in front of the bed. When Jena was finished with the chair she sat in it taking her already hard cock out and positioned it for the next part. Without a word to anyone Jena quickly bent over and took her own cock into her mouth and began to self suck it.

 

[sissykaitlin]

Kelley groaned as he watched Jena sucking her own cock. He reached out playing with Jena's balls with one hand his other caressing Lindsay. "Mm, fuck Jena. That is some trick!" Kelley's lips pressed against Lindsay's neck softly as he said this and he looked up--meeting her eyes.

 

[SRP_lover19]

Lindsay reached out and grabbed his hand while saying "no no you naughty little slut you two already had your fun for now it's time your mistress gets your full attention for now." She places Kelley l's hand on her stomach letting him choose where it went. She wondered where his hand would go on her her large breast,pussy, or ass.

 

[sissykaitlin]

Kelley chuckled to himself as Lindsay called him a slut. "Yes, Mistress. Your pleasure is always the most important!" Kelley hand slowly made its way to her breasts, gently pinching her nipples before he allowed them to cup her ass. Gripping Lindsay's ass tightly Kelley began guiding his thick cock in and out of her. Lifting his head he began kissing her--slowly entwining his tongue with hers.

 

[SRP_lover19]

Lindsay could feel Kelley try to fuck her through her gown and panties. She broke there kiss to say "easy there eager beaver you have to take my gown and panties off first or you will rip them. I would hate to have to punish you on your first day here." She rolled him on to his back and she straddled him as she lufted up her gown. She kissed him again after she took off the gown. She took off her panties as she kissed him hard. When she got everything off she guided his cock toher hole and she slammed down on him hard letting out a loud moan.

Jena could see everything that was going on and she couldn't help but to moan around her cock as she sucked on it. The excitement in the room brought here to her edge of cumming . Wfter a couple of pumps more Jena finally let out a group ot loud moans and yelps as she squirted into her own mouth.

 

[sissykaitlin]

Kelley lifted his hips allowing his cock to properly fill Lindsay and he moaned loudly matching her rhythm he continued to drive his thick cock deep into Lindsay just as Jena began to moan and kissed her back.

Kelley's eyes widened as he turned his head to watch as Jena's cum filled her own mouth. Breaking his kiss with Lindsay Kelley moaned again and looked over to Jena. "Mmm, can I taste you Jena?" Kelley lifted his hips once again filling Lindsay and his hands moved back to her ass, gripping it tightly.