His sissy training (closed)

[SRP_lover19]

Lindsay was laying in bed with her transgender sub named Jena. He sub had originally started out as a man exploring his sissy side and loving the feeling of women's clothing but after a few years with Lindsay the male decided to under go the transformation but kept the cock and added the very large breast. Jena had always look more like a female than a male before her transformation. Lindsay was very happy that Jena decided to keep her cock because she was now getting the best of both worlds. Lindsay knew she had a lunch date with an old male friend that even know she had know him for a long time she could place it but something was off like he was hiding something from him. He was about the same age as her 20 to be exact the only person that wass older was Jena and she was 30 but still look as if she was barely 21.

Lindsay look at her phone and said "we need to get out of this fetish gear and get read I have a lunch date with an old friend and your coming along." She gave Jena's ass a swat before she got up and made her way to her closet. Jena didn't live with her yet but Lindsay kept some clothes there for her so that she could pick out the out fit for the day if they went out. Both girls hurried up and got ready making sure not to dress as sluty as usual because they didn't know if he would mind it or not. After a half hour the girls waited in the spot that he told Lindsay to wait for him at.

 

[sissykaitlin]

Kelley had recently moved to the new city and after having reached out to a number of friends' from university had finally gotten a hold of Lindsay--whom he had shared a couple of classes with. Being in a new place always meant reaching out to old friends to see if anyone was around that could help point him in the right direction of good people and fun.

Kelley's plan for today was to grab lunch with Lindsay and maybe get some leads to see what the pulse of the city was. Slipping into a pair of skinny jeans and a nice shirt, not not bothering with a complete shave beyond the normal cleaning up, Kelley made his way across town on the train. The lunch spot that they had agreed upon was in-between where each of them lived and Kelley always planned to arrive early. Today was no different as he stepped into the cafe and ordered a coffee-- sitting down anxious to see Lindsay again and opening the book he had been reading.

 

[SRP_lover19]

Lindsay was about to leave when she finally seen her friend Kelley. It had been a long time since she had seen him and the jeans he was wearing kind of thrown her through a loop. She didn't know when he started wearing skinny jeans. As she walked up to him she could see that the jeans looked to be a pair of women's skinny jeans but she didn't say a thing because he may have put them on mistakenly not realizing that they were his girl's jeans. She finally said "hey stranger long time no see. I hope you don't mind but I brought along a friend." She points to Jena then says "this is Jena."

 

[sissykaitlin]

Kelley smiled broadly and opened his arms in greetings to Lindsay & Jena. His eyes lingered on both of their lips as he raised his eyes to make meet theirs. "Hi Lindsay! I'm so happy that you reached out to me--it's been way too long and I'm just starting to get acclimated to the city. It's nice to see someone familiar & friendly, finally."

Kelley stuck his hand out to Jena and smiled as he shook her hand. Nervously biting his lip Kelley motioned to the table. "Please, please. Join me for some food and a drink--or is it too early for that?"

 

[SRP_lover19]

"It's fine with me." Lindsay answered for both of them. "What have you been up to?" She asked truly wondering what he had been up to until he reached out to her. Jena sat there not saying a word mainly because she was nervous around new people but Lindsay also taught her to keep quiet until someone said something to her because Jena tended to either blabber on or cut someone off.

 

[sissykaitlin]

Kelley crosses his legs and takes a sip of his coffee. His eyes linger on Jena--who does not seem to want to meet eyes with him. Turning his attention to Lindsay, Kelley bites his lip and sets his coffee down. "Well, I've been working mostly. I came out here for a job and didn't have many other leads so I'm finally finding the time to catch up and doing my best to find people that want to do things with me."

Kelley uncrosses his legs and leans forward. "I've been exploring and trying to have fun but having some guidance would be a very good thing! It's tough not knowing anyone here..." Kelley smiles and runs his hand through his curls as he meets Lindsay's eye. He can tell that there is something between Jena & Lindsay but he isn't sure what it is.

"How did you meet Lindsay, Jena?" Kelley tries to make eye contact with Jena but can tell that she is avoiding his gaze.

 

[SRP_lover19]

Jena looked at him before saying " I met her in a club." She wanted to say more but then felt Lindsay's hand on her thigh. Jena knew that Lindsay was signaling her not to say more. She then felt Lindsay's hand move to her privates. Jena knew that Lindsay was making sure that Jena wasn't becoming hard.

"Sorry she is a little shy around strangers. Like she said we met in a club and became fast friend some would say lovers." Lindsay said and felt Jena's excitement. Lindsay never really labeled them as lovers. Lindsay had a soft spot for her sub no matter how much she commanded her sub. "I know what we could do if you wouldn't mind shopping with some women I need to go to a local lingerie shop to pick up some things you should go with us." Lindsay said grabbing his hand. She didn't know what he was hiding from her but she thought that this trip would bring it out of him if he agreed to go.

 

[sissykaitlin]

Kelley saw the look that Lindsay gave Jena, as Jena began to tell how the two of them had met. Knowing that there must be more to the story Kelley sat back and smiled--chuckling to himself. Kelley noticed that Lindsay's arm had moved under the table but unable to see exactly what she was doing to Jena he was left curious about the nature of their relationship.

"Everyone's shy--but there's no reason to be shy around me. Maybe we'll get a little more friendly as we spend more time together!" Kelley smiles and blushes at his bold suggestion--still not entirely certain if there will be more. But positive that he wanted to spend more time with both Lindsay & Jena.

As Lindsay began suggesting going to a lingerie shop Kelley smiled and considered his options--today was a day off and he had nothing planned but was a lingerie shop appropriate after years of not seeing Lindsay? Shifting in his seat Kelley became quite conscious of the fact that the underwear he had picked out today was a black lacy thong. "Well, doing some shopping would be fun, I think. Is it a special occasion for you two tonight?"

Kelley blushed not entirely certain about being too eager to join Lindsay and Jena. He also knew that he had his own secrets that he wasn't yet comfortable enough to reveal them to the two women sitting across from him.

 

[SRP_lover19]

Lindsay looked at him before saying "no nothing like that it's just that I have some that needs to be replaced. I know you must be saying to yourself that this isn't all proper for me to ask you to go with me but I need someone's opinion besides my lover's." She smiled before she gave Jena a peck on the lips. "If she had her way though Jena would prefer that we walk around naked." Lindsay says caressing Jena's cheek. Jena blushes befor nodding. Jt may have looked to the outside world as if the nodding was forced but Jena didn't really like wearing clothes.

Lindsay could tell that there was something that Kelley wasn't telling anyone and she figured that going to the lingerie shop would be the way it came out. She had always wanted another sissy slave like Jena was before she became a t girl but Lindsay didn't.know if Kelley would be up for it or if he was even a sissy himself. Something about him told her that he was wearing female panties and he was trying to hide it. "We better go to the shop before it closes up on us." She said getting up with Jena. She could see a slight bump in Jenas dress indicating she was getting hard and Lindsay said "Jena dear you better fix your dress it's bunching up on you." Jena blushed harder before she smoothed her dress.

 

[sissykaitlin]

Kelley smiled as he watched Jena and Lindsay interact in front of him. "You two seem perfect for each other! What a lucky pair of ladies you two are--and, I agree with Jena. Life is best spent naked!" Laughing he sat back in his chair--crossing his legs as he did so.

Kelley heard Lindsay's remark about Jena's dress and looked up from the table just in time to notice the slight bump that was evident underneath her dress. Kelley raised an eyebrow but didn't say anything--assuming it was probably just an accidental bump. Kelley stood up slowly from the table making sure that his shirt stayed low--covering his waist line. He knew that it wasn't a big deal but he preferred to keep the thong that he was wearing a secret from the others. Well, at least for now. He didn't know just how embarrassed if they found out and started to make fun of him. "If you two can lead the way I am always happy to follow!"

 

[SRP_lover19]

"Actually if you don't mind I would like all of us to take my car so we can talk and Jena won't be shy around you as bad as now." Lindsay said as she playfully pushed Jena. She grabbed Jena's hand waiting for Kelley's answer. Lindsay could tell that he was definitely hiding something from her and for a second she seen what was a lacy piece of fabric. She knew if it were women's panties that the lingerie shop trip would embarrass him to no end and he may even break down and tell her.

She wondered if he had saw Jena's hard cock trying to stand up undper Jena's dress. She also wondered if he would be up to being her sissy and have a place to be freeish and dress how he really wants to.There was a lot of things rushing around in Lindsay's head and the answers hinged on this trip.

 

[sissykaitlin]

Kelley smiled. "That sounds great! I had to catch a couple of buses to get here anyways. So, with you having a car that makes this a whole lot easier!" Kelley's makes eye contact with Jena briefly and he can feel himself blushing as his eyes roam over her figure. Kelley bites his lip again--a nervous habit that he picked up years ago--and follows the ladies to Lindsay's car.

Kelley was almost oblivious to what Lindsay's intentions were about the trip but knew that he was having a great time and was glad that he had been able to reconnect with her. Kelley still hadn't shared his little secret with anyone (that he was a pantyboi) but he knew that eventually he would with someone. But it was all going to hinge on who was willing to accept it and it would have to be someone that would be willing to encourage and guide him in their adventures. This was promising but Kelley did not want to get his hopes too high--just in case!

 

[SRP_lover19]

Lindsay drove them to an exotic lingerie shop where you could get just about anything a woman would want from probably the world's smallest panties to a a one piece corset. She said with a ring in her voice "we are here!" She really did need to get some more panties and bras but that could have waited till later. She got out in a hurry and got to.shopping right away. after to what felt to her just mear seconds she had everything picked out and ready to be tried on. She made Jena and Kelley wait just outside the dressing room for her. She walked out a bright pink bra and g-string. "Well how do I look?" She asked as she spun around giving the spectators a full view.

 

[sissykaitlin]

Kelley sat next to Jena and couldn't help but glance at her legs. "Aren't you going to be doing some shopping too, Jena?" Kelley smiled and crossed his legs as he waited on Lindsay. The sales woman smiled at them, as they sat outside of the dressing room, and knowingly and smirked. Kelley blushed but was excited nonetheless. His eyes roamed across the room and he admired the panties and other sexy lingerie. Biting his lower lip he turned just as Lindsay came out of the dressing room.

Kelley's jaw dropped as Lindsay stepped out wearing a pink bra and g-string. He knew that almost immediately his cock had began to get firm and as he tried to think of a response he looked to Jena who was just sitting there smiling. "Uhm, wow!" Kelley wiped his lips and his eyes ran up and down Lindsay's body. "You look marvelous, Lindsay. That g-string seems to be accentuating all of the right curves." Blushing and chuckling Kelley, again, crossed his legs covering up his growing bulge.

 

[SRP_lover19]

Lindsay could tell by the way he was acting that she was on the right track to find out what he was hiding from her. She quickly went back into the dressing room and changed.

Jena leaned over and said to Kelley "not today besides the fact that I do like to be nude and thus my panties don't get as much wear I also have to get mine made because my hip are wider than what most stores keep in stock." Jena hoped that she didn't expose to much information to him but she didn't want him to think that she was a Tgirl. She wasn't trying to hide it but she felt right now wasn't the time to tell him.

Lindsay finally came out in a black sheer corset that had flowers printed on it. Two of the flowers just happened to civer her nipples. The corset stopped above her hips and she had on a matching black bikini panties. She could tell from how the clerk was acting that she knew what Lindsay was doing. "Well?" She asked getting their attention again.

 

[sissykaitlin]

Kelley leaned in towards Jena, following her lead, as she started to speak to him. Nearly whispering Kelley responded to Jena's comment. "Well, with your curves I definitely understand needing to order them special." Kelley couldn't believe what had just come out of his mouth and he stuttered to apologize not entirely certain that that was the appropriate thing to say. But he had notice Jena's wide hips and the way that her ass filled her dress.

Being so focused on speaking with Jena, Kelley hadn't noticed that his shirt had risen and that the black thong that he was wearing was plainly visible to the store clerk behind him. But then, just as Kelley started to sit up from speaking with Jena he heard Lindsay as she exited the dressing room, again. Moaning quietly under his breath Kelley bit his lower lip as his eyes went up and down Lindsay's body. "Lindsay, whoever you're buying these items for he or she is going to be one lucky person! You look fabulous and I thought that pink thong accentuated your butt perfectly but this..." Kelley trailed off and he crossed his legs again doing his best to cover his bulge.

 

[SRP_lover19]

Lindsay knew that she only had one more outfit left to try on so she turned things up on him a bit. She grabbed his hand and said "if you like it that much you should feel the fabric it's very delicate and soft to the touch." She placed his hand on her stomach so he could feel the fabric. She looked back to the counter to see a black thong hanging off of the counter and wondered if the clerk was giving her a hint for something.

She soon left to try on one last pair of panties. She didn't know if he was going to crack or if she was going to have to confront him in the car but she hoped that all of her tricks would loosen his lips a bit. She finally walked out in a full length night gown that wasn't as transparent as the corset but you could still see the color of her flesh shine throught the white fabric. She had on a matching Rio thong. "What are you hiding there hmmm?" she asked hoping to get him to accidentally say what he was hiding from her.

 

[sissykaitlin]

Kelley gasped when Lindsay took his hand and placed it on her stomach. Once his hand was on her body and feeling the material he didn't want to take it away. "Oooh, this is very nice Lindsay! You're right. It even feels sexy--however sexy is supposed to feel."

Kelley didn't sit down when Lindsay went back into the dressing room but looked around the area in front of the mirrors. His hands traced over the panties and stockings and they briefly lingered on a sexy pink thong.

Lindsay came out of the dressing just as Kelley bent forward to look at some items on the lowest shelf and his shirt raised up-- but he didn't notice that his thong was now fully exposed. Kelley watched Lindsay from where he was kneeling it felt right to be where he was. "Lindsay, that looks great on you!" Kelley is feeling a little more bold now that Lindsay has so obviously gone out of her way to encourage and comfort him with her modeling show. He looks up at Jena and blushes, "Everything in this shop is so sexy, Linds! I could spend hours looking around here..." Kelley doesn't quite come out and tell them that he would love to be dressed up but he thinks that he has gone as far as he can--still a little scared as to what they would think of him.

As Lindsay twirls Kelley admires the thong that she has picked out and cannot help but stare. "That gown looks lovely on you, Lindsay. I bet you can make anything look good!" Kelley blushes and again looks over to Jena, embarrassed.

 

[SRP_lover19]

Lindsay was glad he had opened up some for her but he still didn't state what he was hiding from him. She quickly went back into the changing room to put her clothes back on. The little show she gave everyone started to turn her on so she hurried to the counter to pay for the lingerie . "Well guys lets head back to the car." She got into the car with the rest of them and when everyone had gotten settled in she looked back and asked "so how long have you worn women's panties?" She began to rub Jena's crotch again but this time she didn't care if He seen it or not. If she had her way She would be sucking on Jena's hard cock right now. Lindsay made sure that he could see that Jena was a T girl so that there wasn't any surprises for him now when he answered.

 

[sissykaitlin]

As they left he store Kelley's eyes lingered on a pair of stockings and a mini skirt that he had liked. But he hadn't had the nerve to make his purchase.

Once they sat in the car, Kelley blushed deeply as Lindsay addressed him directly. Shifting in his seat he looked at her from his seat in the back "Well, uhm, this is embarrassing Lindsay." Kelley ran a hand through his hair and chuckled. "I've, uhm, been wearing them for a couple of years now. I've always had an interest in panties but I guess it all started, yeah, a couple of years ago." From where Kelley was seated, behind Lindsay, he could see her rubbing Jena's lap and his suspicions were confirmed as he watched Jena's cock growing from underneath her dress.

Kelley bit his lip, "Uhm, Lindsay, am I interrupting?" Kelley could feel himself getting excited but knew that all he could do was watch from where he was seated.

 

[SRP_lover19]

Lindsay said to Kelley "no you're not it's fine she likes this. How would you like to live in or have an environment where you can wear what you like all that I ask is that you submit to Jena and I." She didn't wait to hear an answer before she started to move Jena's skirt up revealing her cock and balls. Lindsay quickly took the cock into her mouth and began to slowly suck on the large cock. When she started to suck she heard Jena shift a bit and felt Kelley's hand being moved down Lindsay's shirt to her ample breasts. Lindsay soin felt Jena's hans pawing at her pussy which made her moan out and start to suck the cock harder. After a few minutes of the torrent blow job Lindsay,stops and asks "are you willing to become our sissy?"

 

[sissykaitlin]

Kelley couldn't help but assist Lindsay as soon as she began teasing Jena--his fingers moving to her nipples as Lindsay wrapped her lips around her cock. "Mm, Lindsay, that sounds like so much fun! I would love to be your sissy." Kelley blushed deeply finding it hard to believe that these words were coming out of his mouth. But he was painfully aware of the effect that this was having upon him and he could feel his thick cock straining against his panties. As soon as Lindsay stopped sucking Jena's cock Kelley sat back and sighed deeply.

 

[SRP_lover19]

Lindsay looked back and asked "what all do you shave?" She wanted to know because she made her sissies stay completely smooth shaven all over except for their hair. She didn't like the sissies that didn't shave everything because they look sloppy and unkept. "Also would you be opposed to moving in with me? The reason I ask is because I like for my sissy to be near when I want them." She began to tease Kelley by gently rubbing his cock through his pants.

 

[sissykaitlin]

Kelley smiled and sat back spreading his legs as he did so. "Well, I've kept everything South of my waistline shaved--I shave my legs, keep my ass and cock clean." Kelley scratched his chest. "But, I haven't shaven my chest or face--well, obviously. I am willing I just go to the gym and try to blend in the best I can." Kelley chuckled and moaned softly as Lindsay began to rub his cock through his pants. "I'd could shave my chest though, if you would really like me to."

Kelley sat forward then and thought about the new lease he had just signed. "I'd be willing to break my new lease to live with you and Jena. My landlord did say that if I found something she would be willing to work with me. So, I think I could make that work. I don't have a lot of stuff so you probably wouldn't even really notice me!"

Kelley liked the idea of being Lindsay's live-in sissy and he was quite certain that it was bluntly obvious to her--the thickness of his cock was just the first hint.

 

[SRP_lover19]

Lindsay grinned before saying "just to be clear you won't just be my sissy but you will be Jena's sissy as well." Lindsay stops rubbing his cock and says "well I will get us home so you can start your sissy life with us. I will set things up with a moving company so that your stuff wilk be delivered to my house. I want to test your willingness to submit to me so you and Jena will be pleasuring each other while I get us to the house. You both have the freedom to cum so go nuts the only thinf I ask is that you guys don't do something that will get me a ticket like fucking each other in the back seat."

Jena gets out of her seat and relocates to the back seat with Kelley. She pulls up her dress letting her cock free and then she unbuttons her shirt. She pulls out her large G cup breast from the bra before she unbuttons his pants and fishs out his cock. She starts to slowly rub the cock as she waits for him to make his move.

Lindsay started the car then looked back and said "Kelley if you can she like to have her cock and breast played with at the same time." Lindsay starts the long route to their house.a