Helping Jess Pt. 05

Love

Jess"

She was waiting for me at the restaurant, and she grinned when she saw how carefully I was walking. We enjoyed lunch, talked about several things, then she pulled me into the toilet, and ordered me to strip. She pulled out the handcuffs and put them on me with my hands behind my back.

"and I have a little surprise for you Belle!"

She proceeded to pull out some clover clamps and put them onto my nipples. She looked into my eyes with a beautiful smile, "Belle, can I tighten these please, it would make me so happy to tighten these."

How could I resist her gorgeous eyes and smile, I couldn't so I nodded. She tightened them and I grimaced and squealed, which made her laugh.

When she had finished, she pulled me to my knees and lowered her panties and lifted her skirt, I was soon licking away. Again she used my hair to pull me around. It didn't take long, and soon she climaxed.

She got herself ready, and then at the end, released me from the nipple clamps and handcuffs and told me to keep quiet and get ready. While I was dressing she kept talking. "So sissy, as you know Claire comes over tonight. You need to apologise to her for your behavior and your inability to communicate effectively with her. I suggest you look at her once and then keep your eyes on her feet, she doesn't and will never think of you as an equal and she will get pissed off if you keep eye contact."

She will probably want you to prove you are sorry, I suggest you offer services to her like cleaning her house or her shoes, she'll probably accept that. And remember only talked when asked a question. We'll probably have a conversation, you should not take part in it.

Here are my keys, I see you have been coming in early recently, so I assume you can leave at 4pm. Don't go back home to your house. Go to my house and let yourself in. Once you are in the hall, immediately take off your outer clothes, and try to straighten your stocking and look respectable.

Here is some nail polish, put this on. When I get home, we can do the rest of your make-up.

I quietly absorbed this and cleaned myself up. We went our separate ways back to work.

At 4pm, I left and went to her house and let myself in. I quickly took off my out clothes, and tried to straighten my lingerie. I felt really stupid and nervous. I was going to look ridiculous in front of my girlfriend – well I was getting used to that, but now I would be ridiculous in front of her stunning ex, who also happened to have the key to my chastity belt.

My phone rang, I saw it was Jess.

"Hello Belle, have you arrived and taken off all your yucky male clothes?"

"Yes mistress."

"Good, now find a plastic bag and put all those outer clothes into it. In the kitchen there is a chute leading to the basement. Throw your male clothes into it - you won't be able to get them back without my help.

I simply said "Yes mistress."

"In the future I will install cameras in my house so I can look at you at any time. From now I want you to be like a dog, whenever you see me, you need to show how happy you are to see me and give a huge smile.

I will be home in one hour, there is a maid's dress in the living room. It should be in your size, go and put it on. Also, there is a pair of high heels, put those on too. Then tidy everything up around the house, you need to start thinking like a maid, if anything is messy, you will be punished.

Claire is coming at about 6 in 2 hours, I want you to impress her this time, and to impress her you need to be a really good sissy, OK?"

"Yes mistress."

We hung up and I went and found the maid's dress and high heels. The high heels were simple black – maybe 2 inches, not the prettiest, but still would be hard for me. The maid's dress was white satin, simple but very sensuous, I put it on and felt it tight against my body. My penis tried to get hard again, but couldn't get anywhere – it was so frustrating, probably the most sexual time of my life, and denied continuously.

I put the shoes on as well, and struggled around the house, trying to straighten things as I could, putting things away – it was hard as I didn't know where everything went. The heels were begining to hurt.

Jess came back an hour later, I greeted her in the hall where she ripped off her panties, "I'm horny thinking of how embarrassing this will be for you tonight bitch, get on your knees and lick me out, and make it a good one!"

I did as I was told and she soon came.

"OK, now we need to make you pretty."

She took me into the bathroom and I had to wash my face thoroughly and then shave again. "We should look into whether we can prevent some of this stubble, though don't worry, not through hormones – I want you to be a horny male. Maybe electrolysis or something. Also, we will have to ensure you don't have any hair below the neck, that is really inappropriate for a girl."

Once I had finished shaving, she applied foundation, then also mascara, eye liner, lipstick and many other things I couldn't name. "This will have to do. In the future, I have a friend who is a beautician, I'd like you to go and spend a few hours with her. You can call her and arrange the appointment and tell her what she should do – I will tell you!"

We looked in the mirror, I still looked like a man, but there were elements of femininity there.

After that she made me walk up and down in my heels and dress, she cat whistled at me occasionally. "Look over your shoulder dear and give me a naughty sultry look, and try to look seductive. Wiggle your arse like a girl. Christ you look like a builder, do better or I will cane you."

Eventually she was less dissatisfied and let me rest a little. "Not long before Claire arrives now. Remember to be subservient, and ask for an apology. Then you must always be happy and smiling – though not when it would be inappropriate. You must curtsey and thank her for any comments. You must ask her for advice in how you can be a better sissy. OK?"

Yes, mistress, I will try, but please can I rely on you to protect my limits?"

"Yes Belle, but they will be pushed, Claire is creative and unpredictable. I apologise if I laugh too much or have too much fun. If we go too far I will try and correct it later."

This almost made me more nervous, but I kept quiet.

"Mistress, we still haven't signed anything – do you think something could be done?"

"Yes, OK, I will ask her. Best if you keep quiet and just sign the papers."

With that she sent me into the kitchen to do some washing up, she followed me and told me to do the washing up very slowly and she stroked and groped me, feeling my balls and the straps of my lingerie under my clothes, as well as stroking the satin. It was like being in heaven except of course I could not get hard.

She saw my excitement and bit my neck and whispered into my ear, "Are you getting hot my little bitch?"

"Yes, mistress, I love it when you pay attention to me like this."

"I have to say I love how vulnerable you are my little bitch. Maybe I should chain you to the kitchen in the future. So many ideas of what to do, but they will come."

She continued groping me and the doorbell rang.

"Go and answer it pretty bitch."

I did as I was told, I could see it was Claire outside, I opened the door wide and stepped back, I gave a curtsey and gestured that she could come in.

She looked at me, I looked back. She had such a clear beautiful complexion, the kind of face that mens' jaws drop at. I remembered that I shouldn't keep eye contact with her and looked at her feet.

"Miss Coombes, I apologize for my behaviour last time, I was disrespectful and I am very sorry for that."

"Wow, that's a much better start eunuch, did Jess tell you to apologize?"

Err, how to handle this – I realized probably the truth is critical, "Yes, she did, but I knew myself that I needed to do something."

"Mmmm, then I am not sure this is a real apology from you and not what you have been told to say, what would you do for me to show that you really are apologetic."

"Please Miss Coombes, I am very sorry, if I can I would like to serve you in some way – I don't know how – maybe clean something of yours – your house or car or boots."

Jess came out, they said their hellos and kissed on the lips.

Claire continued "Well sissy, my house can always do with cleaning, so if you could come over at the weekend to be the maid that would be good, but let's talk about how that is to be done later. I have another request for you sissy."

"Yes Miss Coombes."

"Your girlfriend owes me after a recent bet, and I would like to collect on that debt, are you OK with that?"

"Err yes, I don't know, errm." I was stuck not knowing what exactly was involved in this bet, or what this bet even was.

Jess stepped in and helped me out. "John, this is cuckoldry, there would be 2 nights where I sleep with Claire and there will be others involved."

"A lot of others, let's be clear, your innocent girlfriend won't be so innocent, she will be a wanton slut and she will fuck and suck whoever I tell her to." Claire quickly added with a smile.

Jess looked at her, "OK. Claire, we have discussed this and it is OK, just two conditions – firstly that you and I don't get into a relationship, and if there are any men involved, that I don't know them already, and won't again in the future – it mustn't turn into a full on relationship and that is a red line."

Claire responded "Well I think it is clear the first one won't be a problem. The second one – don't you want this little sissy to be a eunuch while you get a proper stud who fucks you regularly?"

My eyes widened at this. Jess smiled.

"Claire, no, we are into the lifestyle but that is a hard limit. Please confirm you agree with this, then you can name the dates."

"OK Jess I confirm. This weekend is the bank holiday weekend so you are not working Monday. So it will be this Sunday night and the following Saturday night. I look forward to it, and I look forward to making you scream with orgasm after orgasm and I look forward to making you a dirty little whore who sucks off and fucks many many men and women, hehe."

Jess looked a bit embarrassed at this, but I think she also flushed as well. She didn't respond to this, just raised another point. "OK, Claire, one other thing, can we do the paperwork for this chastity thing please."

"Yes, ok, it is in my bag, have a read in a minute." She took out some papers and gave a sheet to Jess.

I took my opportunity to address Claire again. I was careful not to make eye contact and I stared at the floor.

"Miss Coombes, please may I ask you to help me."

"Maybe sissy, what is it?"

"I wish to be a good sissy for Mistress Jess, could you help me in that, and give me advice or tell me what to do?"

"Yes, certainly I can help in that, but it will take some time, I suggest you stay some extra time after your maid duties, and you can have some deportment lessons. Meanwhile sissy, my bitch is waiting outside, please call her in."

I went to the front door and saw a short lady there, probably in her late twenties. She looked very attractive, though I could only see her long blond hair and that she was wearing a long raincoat and some shiny red knee high boots with a 3-4 inch heel.

"Please ma'am, come inside"

She quietly came inside noiselessly, not looking at me.

"Sissy, her name is 'Holly', as in Holly the whore. Holly is a simple whore always looking for just one thing. She wants as much cock as possible, she goes looking for men all the time. I had to lock her in a chastity belt because she wants to be a fucktoy so badly, but she doesn't care and now she uses her other holes just to get cock."

The lady flushed at this crude description not looking at anyone.

"So my little whore, I think there is a man here, a rather pathetic man if you ask my opinion – someone starting to find his way into skirts, but still you need to ask your question don't you?"

I got the feeling that she didn't want to ask anything, and that she was embarrassed.

Holly looked me in the eyes and practically begged me, "Please sir, I believe you have a nice fat penis, please fuck me in my mouth or my arse, I need your cock inside me, please make me scream and release your seed inside me."

Jess roared with laughter at this, "Claire you are wicked – I love your games. So how will you answer that Belle?"

I had no idea, of course this had never happened to me in real life, and now the one time it happens I can't do anything, though I suspected that it was precisely because I was in chastity that I was getting such a question.

"I would love to, but I am afraid my penis is not mine currently, it is locked away for 2 weeks."

"Sir, sir, sir, please don't reject me. If I get rejected, my master will whip my cunt for not trying hard enough and being a worthless whore, please do something and treat like the whore I am, please ."

She took off her coat revealing nothing underneath it except a chastity belt, fitted tightly and snugly. She was smaller than Claire and Jess, maybe 5 foot tall only, but beautiful long platinum blond hair that fell down and partially covered her small firm breasts. That together with her red knee boots and chastity belt partially covering her small well proportioned body made her look like a dream – a dream I wouldn't be having. My penis was straining.

"Sir, I beg you, I realize you are not much of a man wearing a dress and female clothes, but I am sure you know how to treat a common slut like me, please feed me your cock, I beg you."

Wow, this was a bit strong and she was clearly desperate.

Jess was loving this, and had started playing with herself, Claire noticed and smiled.

Claire stepped in to help me out, "Well sissy, I happen to have a strapon harness and dildo with me that you could use to fuck her useless mouth, I can lend that to you if you like."

"Yes please Miss Coombes."

This made her smile, and Jess also looked very happy. Clearly they loved the idea of the slavegirl being forced to be a whore, and the chaste slave trying to act like the man he couldn't be.

Claire came back with the strapon, she made me pull up the dress, and helped put the strapon onto me. The dildo was big, probably a bit bigger than my penis and I always thought I was larger than average. I felt so powerless with this dildo where my penis should be and this great looking girl desperately begging for my cock.

With her and me being in chastity belts, it reinforced the humiliation we both had where we had to satisfy any cruel wishes our captors had.

Claire crept up behind me and whispered into my ear "treat her roughly like a common call girl, make her gag, call her names, be the worst you can. If you are nice to her in any way, I will punish her later, and I will make sure Jess punishes you. Act like the man you can't be any more." With that she giggled and moved away to the couch where Jess was now lying. I could see her whisper in Jess's ear, Jess laughed and then Jess pulled Claire's hand under her skirt to her crotch where Claire started to stroke her.

I couldn't stare, I had to perform. "So you want my big fat cock do you slut? How bad do you want it, I don't believe you when you say you want it."

"No, please sir, I do, I am desperate, I need your fucking cock in my mouth or up my arse. Please sir, I need it to feel full, to feel complete. My life is incomplete without cock."

She was really sincere, and it was hard to believe otherwise. Out of the corner of my eye I could see Jess trying not to laugh. Claire had loosened her blouse and was fondling her breasts.

I tried to continue and be as much of a bastard as I could, "Ok, then bitch, let's see what you have, put those pretty lips around my big cock!"

She put her lips around the strap-on and gave the head a kiss and then a lick – clearly trying to tease before starting the action, "you are so big and masculine sir, you have a beautiful cock sir." She gave it another lick like a lollipop, "you taste so good sir, my slutty lips are going to love the taste of your cum."

She looked up at me with a smile in her eyes and tucked her long hair behind her ear. God she looked sexy.

All this got me very hard, of course a girl has never said these things or done these things to me, I gripped her hair and guided her head towards the strapon. She hungrily took it in her mouth, and soon her head was bobbing back and forth over the strapon, taking it deep. She was giving one of the best blow jobs I had ever seen, let alone experienced. It actually hurt as my penis tried to grow and couldn't.

Occasionally she commented "oh you are so big sir, such a big man for a little girl like me." She looked at me occasionally with a wicked glint in her eyes, she was really good!

She was taking the strap-on deeper and deeper. I looked at Jess and Claire and could see that Claire's hand was down Jess's skirt rubbing her. They were both watching us, Claire was clearly amused, though Jess had the glaze in her eyes.

"Suck that dick like your life depends on it, you stupid whore!" Claire shouted out. Her whore tried to take it deeper, but she was beginning to gag.

"Be a fucking man and use her throat for friction, stop being such a prissy bitch!" clearly that was at me, so I took the whore's head and forced it further forward so that the dildo was going all the way in, and her mouth reached the hilt of the strapon. I could hear her gagging as the dildo squashed against the back of her throat.

Claire continued to shout at both of us, I got rougher forcing the strapon as deep as possible and for longer, and then faster. This gagging continued more and more as I got rougher. I heard Jess climax and saw Claire was stroking her gently afterwards.

I wondered how this event would end, of course with it being a strapon I was never going to cum. Then I realized I needed to have a fake climax. "Oh Yes, you bitch" I told her and made my face look like I was on the edge of cumming. "Yes, keep going you bitch!" I let go of her head she kept going, up and down on the strapon.

I faked my orgasm and tried to show a face of pleasure, then I slowed her down and eventually stopped her. I looked at her face and could see that tears had run down her face and made her make-up run. She was a mess, and didn't look too happy, I wondered if I had pushed her too hard, but she wouldn't look me in the eye. I wasn't quite sure what to do.

"She's a good little whore isn't she sissy?" I am sure you'd love to get a real blow job from her, but that's not very likely. Your penis is too small, though maybe it would give her a laugh to see your dimple grow.

I thought this was unfair, I wasn't so small, but I remembered what Jess had warned me about and kept my mouth shut.

"You will get a proper blow job from her some time, but you'll stay in your chastity belt and I'll put spikes in it.

Now, I would like to show Jess something before we leave, so please move that carpet to the side." I did that and saw that there was a trapdoor underneath, I had not known about this and looked at Jess who said nothing and just looked back at me.

Claire had taken out a small chain, and came and sat on a chair close to me. She put a lock into the last link of the chain, she then hooked a finger into the ring of my chastity belt and pulled me to her through the chastity belt ring. She then proceeded to put the lock around the ring of the chastity belt.

"I want to show something to Jess. Crouch over the handle of the trap door. Keep your heels on."

I did so, and she put another lock through the hook of the trap door. She pulled the chain down towards this lock, I had to follow and then she put the lock through another link in the chain and I was locked there. I realized that I was rooted via the chastity belt to have to stay within 6 inches of the handle of the trap door. It was OK for a minute, but then I realized that given I was wearing high heels and now squatting, this could be quite uncomfortable quite quickly. It was very hard to adjust at all.