Helping Jess Pt. 05

Big Dicks

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what was going to happen! Getting back to sleep wasn’t going to happen which was a bit frustrating.

I got up and went into work a bit early, and had several meetings. After one meeting, I saw that Jess had texted me ‘Package and envelope in your top drawer – I suggest you don’t let others see what is in the package :)!’

I found the package and took out the envelope and read the short letter.

‘John, I am sorry I was abrupt with you yesterday, I was a bit frustrated – you asked for her reaction. Anyway I over-reacted with you and apologize.

I’d like to make it up to you, please find a little present for you. Please wear this for me when we meet?



I took the package to the bathroom and opened it carefully. There were several items in there including a red satin suspender belt, some black silk stockings, some red satin French knickers and a red satin camisole. I stroked the material, it felt wondrously smooth, and then my penis tried to get hard again – frustrating!

I closed my eyes and took a deep breath and went back to work, though I soon realized that I didn’t have that long. I finished an email or two and some other bits of work, and needed to change.

I went to the bathroom that had only one cubicle, not a row of cubicles – so I could be sure no-one can look under the cubicle if they were suspicious. I changed out of my clothes and put on the lingerie Jess had given me. It was high quality and the smooth silkiness I could stroke was a delicious feel that made me feel horny, though by this time anything was making me horny. I put my outer male clothes back on.

Walking out of the bathroom was weird, again I felt the satin panties silk rubbing against my inner thighs. I felt the rub of the stockings – smooth and snug. I also felt my package (penis) trying to get hard, and the cage was constantly falling through the lingerie and I was having to adjust frequently. Every little step was not uncomfortable, but a reminder that something had changed.

I was also much more nervous, being at work. Would anyone realize? Could people see the lingerie through my clothes. Could the lines of the camisole be seen? Fortunately I had worn a dark shirt, so it wasn’t easy to see through, but I also worried if some friendly person came and put their hand on my shoulder or arm round my shoulders would they feel anything – very likely yes. It meant that I avoided the more outgoing and friendly of my colleagues.

With my concerns, I got distracted and ended up being 5 minutes late to lunch. Jess was there looking at her watch. She looked great in a dark blue suit with a short skirt, black tights and a shiny white satin blouse.

“I am so sorry I am late”, I apologized immediately, “I am afraid that someone might notice what I am wearing under my clothes, and was distracted thinking about how to avoid situations.”

Jess grinned at that. “Good, that’s a better reason than the normal people give me, and yes it would certainly be embarrassing for you to have to explain that. But what exactly are you afraid of?”

“Well 2 things, one is where the lingerie can be seen from the outside, and then whether someone might put their arm over my shoulder or on my shoulder and feel it.”

“Yes, valid concerns, well let’s test the first one – go to the bathroom – walk slowly so that I can have a good look at your arse, and I’ll tell you if it is visible. Try and walk like a sexy girl for me – wiggle like women do!”

I did as I was told, went to the bathroom and washed my hands, then slowly walked back. I sat down and waited for her to speak.

“Well if I really stare, maybe I can see something, but no, I don’t think you need to worry, but you have given me a nice idea – when you are a naughty bitch and displease me maybe I should force you to wear a white shirt, or even better a blouse and a black bra.”

I think I gave a look of horror as Jess laughed. Then she leaned in and gave me a big kiss, and while kissing me, her hands ran up under my shirt feeling the camisole.

“You also made me realize I need to feel you up all the time, I like the idea of you feeling a bit vulnerable, and when I touch you, you’ll know I am touching you to check you are wearing the correct lingerie and you need to be careful to make sure that others don’t touch you!

I have to say you are pretty today. A nice soft girly feel to you. Now are you wearing everything I gave you? And are the clothes I gave you a good fit – are they comfortable? Are the panties riding up your butt?”

“Yes Jess, thanks I am wearing everything, it is a good fit, well the belt and my tackle is falling through the panties and I have to adjust often, görükle escort but it is a good fit, the panties aren’t riding up my butt.

“Mmmm, pity, I want the panties to ride up your butt, I want you to have a small discomfort all the time, and be constantly reminded of your predicament. This afternoon, I am going to go out and buy a size smaller. With time, I think you’ll need to start wearing a butt plug as well.”

She paused for a minute.

“We also have to get you a whole wardrobe of lingerie and I will choose what you are to wear every day. You will have no say in it, and you will wear what pleases me and be happy with it.

This whole situation has me hornier than I expected, knowing that you feel nervous and that it will get a bit worse for you. How pleasurable! I think we may have to visit the disabled toilet and you can strip and then lick me out. Would you like that dear?”

“Yes Jess, that would be good.”

“Good, good girl. You need to always think of my pleasure, and you’ll need to become a really good pussy licker, I’ll have to get many orgasms to make up for your lack of them.” She giggled at that.

“So Belle, did you bring your male underwear, I want it.”

“No Jess, it is in a drawer in the office.”

“OK, well when we go back, go and get it and bring it to me. I like souvenirs!”

“Yes, Jess.” I was again shocked at how forward she was being, and I was diving into sub space and just following her will. But at that point I remembered many of my fears.

“Jess, I need to ask you, about Claire – is she always like that and can we trust her with the key? How do you know her?”

Jess didn’t talk for a while, then I could see she was choosing her words carefully.

“I trust Claire, and believe she would never do anything to harm me. But be aware she has a temper, so you need to be respectful. She is also a very dominant personality, she likes to tell people what to do and she likes to be in charge and torment people.”

I reflected on this a minute, this was a heavier answer than I expected, “Can I trust her, I mean she has the key to my dick! It is only 2 days and I am already hornier than ever, I can’t see a way out, and from what I see she despises me.”

“Well she doesn’t like men much, she sees them as weak and skirt chasers, and you didn’t start off too well – you just looked at her good looks and didn’t listen to what she was saying. I suggest next time you apologize for your behavior, and listen properly and respond properly, and don’t talk unless talked to. Close your eyes if you have to.”

“Err, ok, but she sounds like a bit of a female supremacist.”

“Yes, I guess she is. She doesn’t have much time for men.”

We sat in silence for a while, she took my hand.

“Look John, she will listen to me and she won’t do anything that upsets me, ok?”

“Does that mean that you need to protect me? Does she know my limits, what I don’t want to do? Can we rely on her to just give back the key at the end of the 2 weeks?”

“Yes, she already knows your limits. But yes, I guess I need to protect you from her, but you also need to keep quiet, she can have a fierce temper – you saw only a bit of that yesterday. In fact thinking about it, I quite like the idea of protecting you – I’ll be the protector in this relationship, you need to keep wearing the lingerie and being submissive. One thing I need to warn you about is that she has a wicked imagination, really very creative. I also need to say that I quite enjoy it at times. She may come up with ideas, and you might not like them, but I will often ask you to go along with them, OK?”

“You’re making me nervous again Jess, will she respect my limits as we have discussed?”

“Yes, silly, don’t worry, we are going to keep this away from work, and family and friends, and I know your limits on pain and that you are not bi.”

This was a relief to hear her say it again. Then she made me nervous again, “but John, she will likely embarrass and humiliate you, and I will enjoy it – a lot, please can you go along with that.”

“Err, ok, but what do you mean, and what is Claire to you anyway? How do you know each other?”

Jess looked away, took her time and then responded, “you’ll find out the kind of things she’ll make you do”, and she smiled. She paused before continuing, “it is a bit early to tell you this, but Claire and I were quite close before, in fact we were girlfriends.”

I didn’t get it, and she could see from my expression, “we were lovers, we fucked, or rather she fucked me as she is always dominant. She was probably the best lover I ever had, physically and emotionally, but I am bi, I like men, in fact I prefer men, and I cheated on her with a man. She was quite upset, and we fell out. Now I have made an effort to get to know her again and here we are.”

I was taken back by this revelation, and then worried again – her “ex-girlfriend” has the key to my cock? How was I supposed to feel consoled by this?

“Jess, isn’t she upset with görükle escort bayan you, how do I know this will work out ok and won’t she lose the key to punish you and not care about me?”

“No John, that would require cold blooded cruelty, Claire isn’t that type, she loses her temper and doesn’t like stupid people, but she isn’t purely cruel in that way. She was upset of course, but that was 3 years ago, we made up a long time ago and have come to an agreement. We value having each other in our lives. I think she is a wonderful positive person, just extremely headstrong and demanding – particularly from men.”

“Err OK, that is good to hear, but I still feel quite nervous with your ex having the key to my chastity belt. Is this a real study? And does she want to sleep with you still?”

Jess took a deep breath before answering, “Yes, she wants to sleep with me, but it is sex, straight and simple, nothing more OK.”

She took both my hands and looked me in the eyes. “John, this has been a difficult conversation for me, it feels a bit early to volunteer all this information so early into our relationship, but I want to be honest.”

She continued on, “look John, I don’t know how far your fantasies go, but there is something else called cuckoldry I’d like to talk about – do you know that and do you like that idea?”

“Woah Jess, this is a bit early.”

She didn’t say anything, and waited for me to talk more.

“Well, generally the concept is ok, though I have some concerns on long term chastity. I don’t like the stories I have read or heard where the girl takes a stud boyfriend, and her previous boyfriend or husband is turned into a slave on a lower level. Intimacy is destroyed and it becomes plain cruelty. I believe in intimacy and being close. I fear that if the girl takes a regular boyfriend – let’s say a stud, then long term the relationship with her current partner will fail. I have never really got it because of that.

I think that sex is important to get to know each other as well, and develop intimacy. I would even say that the partner outside the relationship shouldn’t be repeated, and that it remains about sex.”

“OK, understood, but you are ok for me to have casual sex with men once off? I want you in chastity most of the time, but I do need dick occasionally. To be clear, I want to have a nice big cock inside me to satisfy me as you cannot, and also to make you very jealous and increase your helplessness.”

Woah! My eyes widened, I nodded though.

“OK, good, I completely agree with you not to have repeat male partners. Let me be clear, you are the one person I have the relationship with, and I will not form an emotional attachment with anyone else. Let me say again that I am ok with your limits and I promise not to get into a relationship with any man. But again, I want to be in control – a bit like a control freak and I will use your fetish to be feminized and take it a long long way to force you into female clothes and use that to really control you, and that will be used together with chastity. Another question, do you have a difference between the sexes – are you more flexible if I take girlfriends than boyfriends? Does the thought of either turn you on? What if I invite you into a threesome with another girl, you would have to dress up as a sexy sissy, and you would very likely remain in chastity?” she smiled at this.

“Shit Jess, yes I suppose I am more flexible and I like the idea I guess, the threesome idea seems very cruel, but also like a fantasy. I guess it is ok, though that would be very hard. With girls, I guess I have less reservation, but it is also a slightly more exciting thought. But you won’t go into a relationship with Claire will you?”

“No John, I promise I won’t get into a proper relationship with Claire or anyone for that matter, not like I have with you, but I would like to sleep with Claire, and probably a few times – I hope you don’t mind that.”

“If we can be sure it is not long term, then I guess not, though I am nervous that your ex is holding my key and now it seems she will likely sleep with you.”

“John, you are so special and so gorgeous!” She jumped on me and gave me a deep kiss, feeling my lingerie under my shirt. When I tried to feel her back, she pushed them away, whispering into my ear “keep your hands to yourself you dirty bitch, I am in charge here.”

Once my hands were by my side, she continued with several deep kisses and she groped me, feeling my lingerie and straps. After a while, she pulled away, her eyes were glazed “I need you to lick me out now bitch.”

We paid quickly and left the restaurant. I saw one or two of the waiters looking jealously at me, if they knew the truth they would have laughed at me. I didn’t tell them anything of course, I let it look like I was one lucky guy!

Jess pulled me into the toilet, and made me take off all my outer clothes, leaving me with just my lingerie on, then she smiled at me and took out a pair of handcuffs from her purse.

“I bursa escort want to put these on to my little sissy bitch, so she tries even harder to impress me.”

At this, my penis tried to grow further and I groaned.

“Oh what is it dear?”

I had to tell her that Phoebe was stressing against the chastity belt, and she loved it. “Oh you get off on the helplessness don’t you bitch, that is amusing, I’ll have to work on that!”

She told me to put my hands behind my back, and then she handcuffed me. I felt very vulnerable in lingerie in a public toilet totally at the mercy of this beautiful girl.

She pulled her panties to the side and lifted up her skirt, she pulled my head to her muff and told me to start licking. She was already wet, and I didn’t have too much to do thankfully. She gripped my hair roughly, hurting me, pulling my mouth into her wet crotch. Within a minute or two she was climaxing noisily. I was worried that others would hear, but I wasn’t in a position to say much. She climaxed and pulled my head away while she recovered. I always love that moment after a girl has climaxed and is in that state of euphoria and slowly coming back down to earth. I just wished I could I could stroke her, instead I just kept quiet and waited.

Eventually she looked at me, “that was nice bitch, you were ok, though you need to learn a lot more. Don’t worry, we’ll make you into a good lesbian yet.”

I didn’t talk, talking clearly wasn’t expected. She straightened her clothes and her make-up and made sure she was all ready. She made to go out of the door, then looked at me and laughed at my panic, “Oh, did you think I would go and leave you like this?”

“I wasn’t sure Jess, I was scared for a while.”

“Well, I can be nasty sometimes, but that would be cruel, if you keep trying to please and be a pretty sissy, I will never do something like that. Now let me take these cuffs off, and you can get yourself ready. By the way, this evening I am going out, so cannot ask you over. Tomorrow evening Claire is coming over to inspect you. Please come over to my house a bit early, and I will leave early as well, and we should try and get your make-up done in advance, I would like to surprise her at how pretty you can be. God knows, she needs to see that you can make an effort.”

I just nodded at this and finished getting ready. We soon left.

Later, I thought about all the questions I had asked, and realized she hadn’t answered several of them. I wasn’t sure if that was deliberate or a slip.

Later in the afternoon, I left, thinking I needed to go to bed early, I would always wake up early because of the chastity belt denying my morning hard-on.

Once I got home, I saw that Jess had sent me an email.

Hello my special sissy bitch!

I hope you feel nice and horny! I had a nice couple of orgasms with my vibrator in the ladies thinking about you licking me out. We need to do that every lunchtime I think. I am not sure I told you, but I have a high sex drive. Probably I need to, because you will get very few orgasms, and I will get a lot – the thought of all that denial makes me soooo happy 🙂

Anyway, I bought the French knickers in a smaller size, and I also bought a thong for you just to make sure you get the feeling of something in your butt crack. You will look great!

We also have to think about make-up – have a think and let’s meet again at the same restaurant tomorrow at the same time. Get your tongue ready, and be pretty!

I have put the package into the top drawer of your desk. Immediately you get in, I would like you to put it on, and bring me my souvenir! Make sure you bring me my souvenir by 10am!

Lots of love!



After that I tried really hard to cool down and sleep.

Next morning I woke up early. I had slept well, but the morning wood was frustrating, so it was another early start and visit into the office again.

I found the package and quickly went to the bathroom and changed.

I cleared my email and did a lot of work, and then wandered over to Jess’s desk to see if I could leave her souvenir. She wasn’t there and I was worried about leaving it around for others to find. I tried again a few times before finding her at 10.15am and gave her the package.

She whispered into my ear, “you are late bitch, I said 10am, you will be punished.”

I tried to say something, but it was quite hard in an office environment, and she told me to be quiet.

I went away with my tail between my legs.

The smaller French knickers were tight, I could never get away from them, and it was uncomfortable with the cage slipping out and needing adjustment all the time. Then the knickers were riding up my butt, just as she wanted. I knew that she would laugh and not help me. Indeed, an email came from her.

“Dearest Belle, I hope you like your new panties, I can’t wait to see you in them in the toilet at lunchtime! I hope they are nice and tight, and every step you take reminds you of me. 🙂

I hope they ride up your ass crack, you know us girls have to live with this all the time. By the way, be careful with them, if there is any damage, then you will be punished, no sudden moves and no stretching of the material, you need to move demurely and in a feminine way.

Bunlar da hoşunuza gidebilir...

Bir yanıt yazın

E-posta adresiniz yayınlanmayacak. Gerekli alanlar * ile işaretlenmişlerdir