James Sissy Transformation Pt 01

A married couple. James and Irene. Enjoy

James picks ups Irene from work. They are both teachers. Irene teaches biology and James teaches computer science. They work at different schools. They usually head to the gym after work. They work out and head home. They been making small talk, asking about each others day. They get home, cook tea, have a shower and head to bed. Irene is feeling a little horny

Irene : so.. How tired you are... I mean really?

James : What you mean?

Irene : Like.. Tired? Or.. TIRED

Irene puts a little emphasis on tired to mean sex

James : are you horny? He chuckles.

Irene : yeah a bit..

She turns the lamp off on her bed side and snuggles up to him, spooning him, naked. Irene slowly starts stroking James's 6 inch cock.

James : mmm

James puts his head back and Irene kisses him on the mouth, sticking her tongue deep in his mouth. James loves when Irene dominates him. She's very sexual and James doesn't feel that sexual at times, but he loves having sex with her, it's just she can get very horny, every day. James starts to get hard, as he loves Irene stroking his cock. He hasn't touched her, and she's stroking his cock with one hand and grabbing his balls with the other hand.

They undress

Irene climbs onto of him. And enters him with 6 inch cock, but doesn't put it all the way in, just half way, with his head just touching the entrance of her pussy.

She then slowly starts to fuck him, slowly picking up the pace. Irene loves to dirty talk but James is more plain, so she asks him,

Irene : Am I fucking you good?

James : mm yeah

Irene : I wanna hear you talk dirty to me, she says in his ear.

James : Oh.. Um...

Irene : Say your hard cock loves being in my tight pussy... Say my pussy is wet, you feel it?

James : I love my hard cock being in your tight pussy

Irene : say I feel wet

James : your pussy feels wet

Irene : thats a good boy

James loves her being more dominant.. She slowly starts to go faster

Irene : You gonna cum in me baby?

James : Mmmm I love fucking your wet pussy Irene... It feels so tight.. It feels so good...

James loves sex but often has little sex drive and isn't a sexual person but he loves this. He knows it's going to take him a while to cum

Irene : hun.. I'm sorry I'm.. I'm close.. Are you close?

James :no.. Sorry hun it takes me ages..

Irene : I can't hold it... Oh James! She's going very hard at this point, about to climax

Irene is very loud in the bedroom

She's thrusting deep and fast now

James : Irene.. You cum baby.. You know me.. Sorry.. You just cum tonight

Irene :.. Fine.. I wish I could wait.. But.. This cock is too good.. Oh..

She starts to cum, very hard, moaning very loudly

Irene: OOOOOO!!!! Oh.. Yeah.. James.. Your cock feels so good

She's breathing very heavily

Irene : Oh baby that felt so good.

She slowly pulls out. She kisses him very deep in the mouth again

James : That's ok babe I'm glad you came

Irene : Thanks hun. Sorry, it's ok.. I want to make sure you cum tonight as well though, as I haven't gotten you off in ages

She gets off James

Irene : you want a bj?

James :it's ok hun.. It's late and it takes me a long time, I'll try next time

Irene : OK hun

Irene gets up, grabs her phone and climbs back into bed.

They lay on their backs.

Irene wishes James would cum

They kiss and go on their phones for a while. James says night and goes to sleep

Irene stays on her phone for a while and gets a little horny when she sees a sexy man on an advert. She loves read sex stories so she goes to literotica.com, slowly stroking her Pussy while she reads a random story. She opens a random story. It's a story about a women turning her husband into a sissy who gets fucked by men. The man goes into chastity. As she's reading it, she gets extremely wet. She's surprised she likes this. It's a slow story in several stages. Irene gets more and more turned on. She feels really wet.

She looks over at James, he's sleeping soundly. He looks really cute and vulnerable. He has a very boyish look. He doesn't look like a man who fucks her. His skin is pale white, not muscly and a bit chubby, very average and shy, not the sort of man dominates women. She starts to imagine turning James into a sissy. As she's does she cums hard. Her pussy starts gushing and she moans out loud

Irene : Ohh!! Mmmm! She keeps fingering her self fast. Her legs twitch hard. She orgasms again and again. She cums really hard. Her orgasm last about a minute

She's breathing heavily and trying to be as quiet as she can.

She calms down from her orgasm, slowly catching her breath. She's shocked that idea turned her on so much. She goes to sleep, hatching a plan. She goes to sleep. The next night she starts a little step for her plan. They are both in bed

Irene : Hun..

James : Hmm?

Irene : So I was reading online.. There was these new toys I saw and.. I think it might help with you being able to cum, she says hopefully.

James : Yeah? OK hun

Irene : There is this little butt plug... It helps when men ejaculate

James : up my bum!?.. Isn't that Gay!?

Irene : No.. I mean.. Maybe.. A little.. It just stimulates the prostate... I just thought I would mention it. You know.. For me... I just want to feel you cum deep in me... That's all.. You can just use it to help.. You know.. It might help

James : I don't know.

Irene : You said you wanted to cum in me... It will help

James : I don't know

Irene : I just wanna feel you cum in me babe.. We haven't for a long time, please?

James : OK hun I'll give it a try

Irene : great!! I ordered a couple of them... In different sizes...

James : you already ordered!?

Irene : I just got one size and.. You know... We will go small..

James : I don't know.. Up my arse... It's weird

Irene : Please, it's for me and us?

James : I don't know if it will do anything. But I will give it a try hun... For you

Irene : Thanks hun. It should make you cum.. I'm sure

James : OK

They go to bed

Irene : We can start tomorrow.

James : OK.. If you think it will work. I want to cum in you

Irene : thanks hun

They go to sleep, James with a bit of dread that Irene will be sticking something up his arse. He isn't the most sexually driven man, so it will take some convincing, but he's happy to help. James loves Irene.

Next day they get home. They shower, have dinner and head to bed. Irene goes into their bathroom, picks up a small black butt plug.

She brings it out into their room. James sees it as he's getting out his pj's. It's just a black bulbous shaped piece of rubber, it's only 2 inch's. It's not very big. But James hasn't seen a sex toy in his life

James : I'm not sure if I want to..

Irene : come on James.. Please try.. We are just going to put it in... It's small

James : I don't know if it works hun...

Irene : I'm sure it will work hun, she says convincingly, stroking James's hair and cheek

Irene has a seductive way with her tone

James : Fine hun, I will do it for you

Irene : great, she says, giving him a hug and a kiss, stroking the back of his head. James loves the attention she gives him.

James gets on their bed on his stomach

James : ok I'm ready

Irene : Oh I don't think you are quite ready yet hun.. You need some lube first.

She goes and gets a bottle of lube

James : It's a bit cold..

Irene : It will warm up James, just give it a second.. She has her hand on his bum, holding it, giving him a bit of support. It's really helping James as it makes him feel more relaxed.

She rubs lube onto his bum cheeks and slowly slides a finger on his crack

James : it's a bit weird hun.

Irene : It's ok hun.. I know it feels weird now.. It's just you doing this to help us out hun

James : yeah. I hope it helps

Irene : thanks hun, it will, trust me..

James : Ok

She slides her finger down his bum and touches the rim of his anus. He flinches a bit. She slides her finger around in circles around the rim. James doesn't love it at first, but it starts to feel good. He likes when she massages his bum. He has never had it done before. James is still on his stomach on the bed

James : Mmm

Irene : see it feels nice doesn't it

James : yeah hun...

Irene : ready for the plug

James : ok hun, just please be slow

Irene : of course hun.

Irene takes her hand and spreads James's bum cheeks apart and puts lube on the rim. She then puts more lube on the butt plug

Irene : ready hun

James : ok.. Slowly.

She slides it into his hole, slowly pushing it in.

James : Oh god, it feels so weird

Irene : you are doing well hun.. It's almost in, just another little push and it should go in.

Irene is getting so wet. Her first part of her plan working

Irene : ok hun.. Almost done.

Irene slowly pushes the rest into James

James : oh.. That feels weird

Irene : You doing a great job hun, just relax.

James feels so weird, plugged. But his cock is rock hard.

Irene : omg look at your cock. It's rock solid.

James feels extremely embarrassed

Irene : look how hard it is.. I need it!

She pushes him onto the bed

She pushes into his cock. It takes her breath away. It feels so hard

Irene : omg.. It's so hard and stiff. Oh James your cock feels so hard in me.. This butt plug is doing a great job!

Irene rides him hard.

Irene : James!.. It feels so good in me. I'm going to cum.. Hard... You going to cum too!?

James : I dont know hun

Irene : you can.. Oh... James! I'm cumming!! Oohhh!!

She has an intense orgasm, James cock just feels so good in her. It feels so big and hard, she just rides it fast

Irene : OOO!!!

She collapses. The cock still in her. Still erect. She catches her breath. It was her best ever orgasm. Also knowing part 1 is complete, James's first anal experience.

They kiss passionately. Irene is in bliss, so happy her plan worked

James : That was a nice one hun. You rode me good

Irene : Thanks hun...any closer to coming?

James : I'm sorry hun it's just takes me a while, he says disappointed

Irene : Don't be sad hun... I had a great time. Your cock is so hard!

James : thanks hun

She pulls his cock out.

Irene : you want me to take the plug out

James : Yes!

Irene : I don't know... Maybe we should leave it in

James : hun come on. I don't want a butt plug in. It feels weird.

Irene : OK hun I'll take it out.. I think you did a really great job for me.. So good. She kisses him again, long and passionately, her hands rubbing the back of his head.

James : Thanks hun. I'm glad it helped you out

Irene : It was great James, you made me orgasm so hard. You really helped me hun.. She strokes the back of his neck with her hands

James : I'm glad hun

Irene : Your cock is still hard

Irene says with surprise

James : I am a little tired

Irene :no worries hun

She slowly pulls the plug out. They head to the bathroom and clean up. They kiss and go to sleep

The next day goes as normal and they shower and get into bed. James is a little worried Irene wants sex again. He's quite tired and feels a little horny

Irene : you doing ok hun?

James : yeah I'm alright. I'm just tired

Irene : you doing ok.. With last night and...

James : I'm ok, yeah it was weird.. But it made your feel good

Irene : yeah

She reaches over and hugs him. James loves how cuddly Irene gets sometimes

Irene : You did well James, thank you... She strokes the back of his head

James : No worries hun.. Anything for you.. I want to cum for you as well.. I just hope this is the thing that does it.

Irene : yeah.. Well it's just one night..

James : yeah.

James kisses her and they hug a little. James feels relieved Irene isn't horny for a change. He can't help but think that this thing will help him cum. They both read for a bit. Irene is reading a sex story again. She's getting wet. She sneaks her hands down under the sheets and slowly massages her pussy. She's reading the sex story about a women making her husband into a sissy and turns him bisexual. The husband starts off as straight and the wife has to train him into being bi. In this scene the women makes her husband wear lipstick. As Irene reads this, she starts to slowly finger herself. Trying it hide or from James. In the story Irene learns more about sissies. That they wear chastity device. This thought thrills her

Irene :hun..do you mind.. Sorry ill be quick hun, but I need to get off

Irene slowly gets up, goes down the bottom of the bed, she takes the covers off. James cock is erect, rock hard. Irene starts to stroke James cock

Irene : You mind if I go hard and fast.. I'm horny hun, I'll try and be quick

James : that's fine hun..

James loves when she goes fast and hard. James is slowly stroking his cock as she rubs it

Irene : I'm getting close hun

She gets on top of him and pushes down his cock fast and hard. She is really horny, so wet

Irene : James.. I'm.. So horny

She thrusts harder

James : yeah

James likes going slow but when she goes hard like this, he can't get enough.

Irene :oh hun..let me get the butt plugg.. I'll do it. She pulls his cock out and runs to their bathroom, picking up the small plug, and a bottle of lube and runs back, she jumps on him and jumps on his cock. She slides it in. James arches his back, a little in pain as she rides him fast

James :oh..

Irene : sorry hun..

Irene thrusts up and down his cock as fast as she can. She has an intense orgasm as she does this. She cums hard. She loves how fast her orgasms come. She never thought she was a nymphomaniac, but lately she just seems to always be horny, but James cock always makes her cum really fast

Irene :any closer to cumming?

James : I don't know, I can feel it building in my stomach

Irene : just tell me if it gets too much hun

James was getting closer. They clean up and head to sleep.

They do this for a week. Irene keeps doing the same things. Every night they have sex, then plug his arse with the small plug

Its a Friday and they get into bed. Irene as bought a new plug. Quite a large one. She has been reading the sissy story every night before bed, getting horny, fingering her self. She's also been thinking about how to get James bi, and more into being a sissy

Irene :hun.. I have a new plug she says nervously. I think we should start to slowly increase the size... It should make it easier

James : bigger than the last one. It was only small

Irene :yeah it's about 5 inch..

James : oh.. Blimey hun.. Isn't that too big

Irene : I just wanted to try and.. We should slowly get your body used to it

James : hun.. It's pretty big..

Irene :I know..but it could help

Irene goes off and returns.

Irene :bend over hun.. She gently grabs the plug

James :you going to be careful hun...

Irene :I will be hun

She lubes his arsehole

James : its cold

Irene :I know hun

Irene slowly pushes the plug in

James : Oh my! Urggh it's big!

Irene :Sorry hun.. I will go slow

Irene keeps pushing the plug in slowly

James : oh God, it's so big..

James feels extremely horny as it enters his anus but tries to hide it.

James : Urrrgh.. OMG it feels so weird hun.

Irene : It will get used to hun, don't worry. You doing really well hun. She is massaging the side of James arse with one of her hands while slowly pushing the plug in with the other hand. Plop it goes in. James arches his back. He can't help but groan, a little in pain. Irene leans in and gives him a kiss, still rubbing his back and arse cheek. James is getting extremely hard.

Irene : God look at this cock. It's like a rock.

She pushes him down on the bed. Sliding him in

James :oh God, it's so big. I'm so full..

Irene : It feels amazing James, you're making me so wet, your cock is so big... It feels so good...

Irene thrusts him deep into her, as James feels a rush of hornyness over come him. He has never been this horny in his life. The butt plug is rubbing his prostate. He moans in embarrassment

Irene notices his face. He seems to be enjoying himself.

She starts thrusting faster

James : Oh.. Urrrgh.. I feel a little funny hun

Irene : it's ok hun.. you just relax

James : I don't.

James is almost moaning like a girl. Very feminine moaning as his cock starts to twitch. This feeling of the plug hitting his prostate is sending waves of hornyness into his body.

James :Oh Hun, it feels weird..

James arches his back..

James : urghh

Irene is so wet feeling James turning into a sissy Femboy. She feels is cock getting harder.. Like he's going cum..

Irene :omg hun.. Are.. You...!?

James : urrrgh, yes.. Oh my..

Irene : you're cumming, James! You're cumming

James :I think so! Oh my!!

Irene : you can hun, it's ok, she says softly.

James : urghh!! I think I am!!

James has a long, slow and hard orgasm.

Irene feels the cock pulse so hard as James is moaning like a girl. He has a large load. Hes involuntarily riding the butt plug. Irene cums instantly. It's the first time she cums with James, usually James doesn't cum and they stop. This time they are cumming together

James : I came hun I came!!

Irene starts kissing him and crying. James is feeling the biggest orgasm ever, and Irene is feeling so much love for her man

Irene :you came hun, you did, it's ok.. You did.. It's ok hun, it's ok..I love you so much.. So much. They kiss passionately

James : hun it's so amazing...I can't believe it. I haven't came in a years! It's feels so amazing, hun..

Irene is so happy and crying and kissing him. They are in pure ecstasy and kissing and hugging each other, so much love is in the room

Irene : hun...I love you so much. She strokes the back of his neck and back..

They clean up and head to sleep. Cuddling

They next few weeks they fuck each night. And James cums hard every night

Irene is deciding how to turn James more along her plan.

They are laying in bed

Irene :hun.. Do. You ever wank?

James :What.. hun? No

Irene :ever play with your self

James :yes.. But.. Only when your not around

Irene :I'm just wondering hun.. What do you watch?

James :what..?

Irene : What you wank to

James :um.. Well

James gets red in embarrassment

James :I just use porn

Irene : ok hun.. Well what porn

James :well hun, it's not always the same, he says, still very embarrassed

Irene :its ok hun, tell me. I wont be angry

James :well sometimes it's regular porn

Irene :yeah hun

James : well I have started to wank to lesbian porn, it's nice seeing two girls

Irene :I see. Anything else

James :and.. Femdom porn he says embarrassingly

Irene :hmmm.. Interesting, hun. She gets closer and hugs him tight

Irene : thank you for telling me. I just want to help out. Could.. I wank you off.. While you watch?

James :oh..hun... Ok

Irene : great! I love you hun.

They kiss. Irene starts stroking his cock, then moves her lips to his. They kiss as she slowly wanks him

James :hun..I'm a little embarrassed.. I've never had anyone wank me before

Irene :It's ok hun. Just relax. She says softly, in his ear, with her hands running over his body, giving him soft kisses

James :OK

They kiss more

James : It's a little weird, but ok.

Irene passes him his phone. He brings up the lesbian video. They lay and cuddle as James starts to get into the video.

Irene : You liking that hun

James :yeah hun... This is really nice hun.. But your wanking me off

Irene : I just want to help out

They kiss some more

James :yeah.. This is really nice... Thank you hun. You're so sweet

Irene is watching the video of the two girls. The girls start to make out.

James : ooh... They kissing. This is hot