Tina Rules! Ch. 3

Story Info
The training continues with a twist.
4k words
4.18
86.6k
00

Part 3 of the 3 part series

Updated 09/22/2022
Created 01/16/2002
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jimmysub
jimmysub
21 Followers

(In the first two chapters jimmy is discovered to have visited some fem Dom sites on his computer. Tina his wife with her young co-worker Lydsay begins to train and emasculate him. In this chapter jimmy's past comes back to haunt him.)

Tina sent me to my room after I had satiated her. She gave me instructions on how I should be up earlier then her so that I could make breakfast for her. Friday dawned as a beautiful summer day. Still using a vacation day I was staying home to continue doing housework. I expressed some misgivings about her actually going on a date the next day and whether she had been kidding about my buying condoms and contraceptive foam. She said no, she intended to indulge my fantasy life and help me learn that my role from then on would be more of a companion, kind of like a well-regarded dog, and servant to her.

If I found it unbearable we could always divorce and I would be free to leave. I think you'll get use to it. I like you a lot but I really do need a more macho guy in my life. There is nothing wrong with being a loving and compliant person as long as you do it with energy and enthusiasm. Besides you have to admit that there is that part of you that wants this as well. Those sites you spent your time on the Internet all seemed to have that consistent theme. It was not as if you stumbled across them by accident and quickly left. Cheer up! Hon you'll make proud of you I'm sure.

It did feel weird buying condoms, as well as picnic supplies for a date my wife was going on with another man. The lingerie store was embarrassing as well. She had placed an order over the phone and actually bought Lydsay a special gift as well. But she told the clerk to be sure that I left the store with at least seven pairs of panties for myself. The clerk picking out a bright red pair held it up to my blushing face see nice match for your complexion.

I returned home went out to get her bike fixed up. I called her and reported that I accomplished my shopping mission. I admitted that I was still in my boy clothes and she suggested that I get the lawn mowed before changing into my chore outfit.

Friday evening after dinner and a swim I helped Tina get ready for the next days adventure by trimming her bush and giving her a nice pedicure. She asked me if when I read the stories on the net about guys doing that whether I found it exciting. You know the poor wimp husband gets his wife all sexed upped for another guy with the hope that if he's lucky she'll return home with a well-fucked pussy. I said it was nice as a fantasy but I always had safe sex concerns about the reality. Well that's why you bought me condoms. She assured me that she would be cautious about exchanging body fluids with someone.

Before sending me to bed early she had me hold a vibrator so she could "practice" having a large penis in her mouth. "Just like riding a bike once you learn you know how do to it". She had rarely gone down on me. She explained that I was never macho or forceful enough for her to do it to me. "It is one of my fantasies to have this big macho guy make me get on my knees and please him before giving me a nice fuck". She explained to me. She put me to bed early so that my last night of freedom was long. She even started me off taking my penis she rubbed it over her neatly trimmed bush. Would you like to try giving me a nice satisfying fuck? I said sure please May I. Well you remember the deal if you come before I'm satiated when your chastity goes on it will stay on for six months.

Well maybe I better not I replied.

"So are you saying you don't want to fuck me"?

Well six months is a long time.

"But what am I going to do?"

Well I thought you were going to start dating.

"I am but I'm still married to you. Do you really want another man to take over this responsibility?"

Yes I understand you have needs that I can't fill so yes get a boyfriend.

Say Please!

Please Tina find a man who can give you the loving you need. It's fine with me I just want you to be happy. She was handling my cock throughout this conversation and some pre cum had discharged. She got up told me to wait and not play with myself till she returned. When she returned she had ice wrapped in a face cloth and iced me down. She explained that Lydsay suggested that my endurance could be developed if I was brought to the edge of Cumming and then iced down. That girl has a million tricks up her sleeve.

She pulled up the panties of my baby doll with the ice still in them.

Since you don't want to fuck me perhaps you would like to eat me out. I readily agreed. The ice slowly melted as I brought her to a number of orgasms. I know I had done a good job because 15 minutes into eating her out she through down the book she was reading and wrapped her thighs around my head.

After she went off to bed I changed the sheets and had a good jerk-off session with myself. SATURDAY

I brought her coffee in bed. She patted my prick and said you be a good boy now. Hopefully I'll see you in a week or so. I changed into my street clothes and waited for Lydsay to pick me up. She got there a little after nine, just as Tina was coming out of the shower in dressed in a nice top but with this pair of bike shorts on that left little to the imagination. They made arrangements that Tina would call at about 5p.m. or so and let us know how things were going. Lydsay was told to indulge herself at my expense and that I should indulge myself as well. By the way you will be turning over your ATM and credit cards so that I can guide you to financial maturity Tina announced.

Lydsay looked so hot. She had on this summer outfit of short shorts and halter that left her midriff exposed she had this sandals with a nice heel. Tina reminded me to be respectful and cooperative to her adding that once my chastity went on she would have a say as to when it came off. In fact if Lydsay wanted she could be my orgasm control manager. She seemed to be amused and happy with this little joke of Tina's. I had packed an overnight bag with a nightgown and a change of clothes in case things ended up working out that way.

It wasn't till we were walking to her car that she commented on the nice pink panties I was wearing as they could be seen through the white shorts I had on. Of course she didn't let me go back and change. We drove to Old Town and the shopping district where Eros was. Though a parking space was available right in front of the store she parked further down the street. I started to walk next to her up to the store. She very curtly explained that when we were out in public I should walk a few deferential steps behind her.

The woman who was running the store greeted her like a long lost relative. After some small talk and how have you been where have you been Debby asked what she could do for her. Well jimmy here needs a tube. We went to the back room for a fitting. Debby and Lydsay had a little joke about whether I wanted a permanent one or one that could be removed. When I was out of my shorts and panty Debby remarked probably a boy's medium or a men's small. The boy's medium ended up being the proper size. I had gotten hard and was iced down for the fitting. Debby explained that I should be grateful that I was just getting a simple tube. She showed me one device that regulated arousal by having a half of dozen pins sticking in. If aroused the pins did the trick of curbing desire.

Debby casually mentioned that putting super glue in the lock would make it permanent. Lydsay remarked that back in high school she use to tease the boys about super gluing it, but had never actually done it. Finished with my fitting and dressed again we browsed through the store. Debby showed this Dildo/harness set up that had become popular. It fit over the shoulders kind of like a bra. Where the dildo sat on the person's chest and he could be ridden to ecstasy. I was fitted with one and Lydsay picked out a couple of dildos one for her and one for Tina.

We left the store. On the way home we stopped so she could do her grocery shopping. She explained what she looked for and liked as she expected me to learn to market for her.

The Past Comes Back To Haunt

We got to Lyndsay's apartment, which was in a small two family. Her landlady was out working in the yard when we pulled in. We recognized each other in the same instant.

She said what is he doing here? I really don't want him on my property. About 12 years ago Lauren and I had a brief fling. She ended it abruptly and I was a jerk about it. I had spent a month or two hassling her and trying to embarrass her. She threatened to get a court order and I came to my senses. We wearily eyed each other for a few years but basically kept a lot of space between us. We then fell out of the social circle and I had not seen her in like ten years.

Lydsay asked what the matter was and Lauren said you don't need to get involved with this jerk you can do better. Lydsay said let's go inside and talk. We went up to Lydsay apartment still cluttered with boxes. Lydsay offered Lauren one of the chairs and took the other saying "kneel boy" to me. Lauren explained her grievance and I acknowledged that I had been a jerk. Lauren seemed to lighten up as Lydsay told her Tina had lent me to her to help get the apartment organized. I am also kind of baby -sitting him as Tina went off for the day with a real man.

Lydsay said check this out. Jimmy undo your shorts. Lydsay explained to her that I was a little sissy so I wore panties. She actually smiled when she saw them. Now pull your panties down and show Lauren your pretty little chastity.

"Oh that is great. I've seen them on some of the boys that date Sara I have not seen one on an adult, if you can call him that," Lauren remarked.

Lauren asked Lydsay to tell her the whole story but Lydsay deferred to me. Start by telling her what size you got. I stammered out I have a medium boy's chastity. I got it out that Lydsay had heard about my wife's decision to start dating. She encouraged Tina to "fix" me so that she'd feel safe around me. My wife Tina has been dissatisfied with me as a lover so she needs to find a better one.

Lauren asked "do you still cum in record time?" I admitted that I did.

Well you can be on my property but there is a little matter of payback.

Lydsay suggested that I kiss Lauren's feet as a matter of apology. I had to beg and plead to actually be allowed to do so. I complimented her on her lovely feet but she told me to be quiet and attend to what I was doing. Lydsay excused herself returning with a riding crop. I've had this since my horsy days perhaps Lauren you could find a use for it.

Clapping her hand and smiling I know exactly how I would like to use it. I was positioned over the chair she had just vacated, kiss where my ass just was. While doing this I got 15 whacks by Lauren. Lydsay told her to think in terms of paying me back over time and not to make me take my punishment all at once. When she stopped and I fought back the tears Lydsay told me to thank Lauren for providing me with the discipline I needed. I did so. Lauren said well I think things will be different this time around. You are never forgetting that I am in always superior to you. While I won't interfere with Tina's property rights to you there are ways that I'm willing to help train and discipline you.

Well pull up your panties you have work to do. "If I knew about Lauren I would have had Tina send you over some of your new clothes." Lauren asked what she was talking about. Well at home when he does housework he has some of his sissy clothes to wear. But since he is going to be running back and forth to the garage to throw stuff away I figured I'd have him keep his boy clothes on.

Lauren replied that she might have something for me to wear. She returned momentarily with a black skirt." I picked it out special for you. It is a nice wool skirt might be a little itchy on a hot day like today. Lets see if it fits." It was kind of tight. It was decided that I'd benefit from the full effects of the wool if I didn't wear panties. Lauren remarked that she had a left over home waxing kit that maybe later my hairy asshole could be treated. Lydsay said yeah I tried one of those once was that ever painful. Let's do it later.

Lydsay had a pink tube top that I squeezed into. The outfit brought tears of laughter to Lauren and tears of embarrassment to me. Before she left she offered Lydsay a deal that every time I mowed the back yard she would deduct some money from the rent. Sure once it cools off later I'll have him do it.

I got down to work. Lydsay had a lot of books to unpack. She just sat around and listened to music. I asked for a drink of water and she filled a bowl and put it on the floor for me to drink out of. She had a fan but it was still hot and the more I sweat the more uncomfortable I became in my skirt. Lydsay finally went out to sit in the shade. I was nervous and awkward going back and forth from her apartment to the garage.

Lauren had joined Lydsay outside and she continued to have a devilish smile anytime I walked by them. Even when I was given a break they had me lie on the lawn in front of them Lauren would use her foot and toes to tweak my pee pee. She had gained some weight over the years but was still attractive. During my break the conversation turned to what Tina was doing and how much fun she is probably be having with a real man.

Lydsay was making dinner for us when Tina called. The outcome of the call was they had ridden their bikes 30 miles out of town and just before turning back had found a little B&B they decided to stay at and return the next day. Lydsay handed me the phone and Tina said "I really don't have time to talk right now just be a good boy for Lydsay I'll tell you all about it tomorrow". Tina said we could go back to the house if we wanted to go for a swim.

Maybe Sara's home and the four of us can go over swimming.

Sara?

Yes, Lauren's niece has been living with her for a couple of years. She was at work today so you haven't met her. We concluded our dinner. Lydsay called Lauren to tell her we had a pool to go to. Sara turned out to be a recent high school graduate who had nice Italian good looks and nice long legs. "You must be little jimmy the wonder houseboy" she said by way of introduction. Lauren mentioned to Lydsay that she had found more clothes for me to wear. Well he has been scratching like mad in that skirt maybe its time to give it a break. Sure I've got just the outfit for him. I stripped in front of Sara. Who said look it the little weenie all locked up in its little tube. I don't think I've seen a prick so small since Jr. High. Lauren returned with this pink sundress that tied around my neck with a short frilly skirt. It felt so good to be out of that wool skirt. Sara seeing the marks from the crop on my ass commented well looks like some ones been a bad boy.

Sara had a pair of sandals that fit me. Lydsay said go put on some panties. Sara said "no I want access to those balls. There is nothing I enjoy doing more than blue balling boys in chastity tubes." I had to kneel on the floor of the back seat, as Sara didn't want me sitting on the same seat with her. She asked if the pool was private. Yes Tina and I seldom wore suits in it.

Sara asked who is Tina?

She is my wife.

How could you have a wife, where is she?

She went on a bike ride with a friend and they are staying up north and riding back tomorrow.

Is it a girlfriend she went with? Lauren piped up.

No it's a guy she knows from the gym.

Sara teased me about how Tina probably would of raped the guy by now getting a good fucking for the first time in a long while. I bet she'll come home really happy and satisfied for a change. Fortunately I don't see any neighbors as we pulled into the driveway. Lydsay instructed me to go and get some towels and cold drinks. When I returned poolside they were all swimming topless.

Sara said hey blue balls imagine six tits and you lay as much as a finger on them you'll be sorry. I asked Lydsay if I could swim.

She told me to hold my horses and not get too excited.

Sara said horses; "lets play horses, Lydsay and me against the sissy and the aunt." Lauren hesitated until Sara mentioned imagine how blue balled he'll be with you on his shoulders. I got out of my sundress and Lauren sat herself on my shoulder. Give me a few minutes to break him in. I carried her around the pool and she explained if I was a good horsy maybe someday I could pull her around in a cart.

Sara was right when we got into "combat" it was very erotic for me with Lauren on top and Sara who is taller than me rubbing her breasts in my face. Lydsay and Lauren seemed to be playing tit squeeze with each other as much as trying to knock each other off. I was getting tired. When the game was over Sara very seriously reported to Lydsay jimmy was very fresh to me while we were playing. You heard me say "my tits were off limits to him and he kept trying to kiss them." Lydsay said "you were a bad boy when we get back I think you'll get another cropping."

Sara piped up if you want I'll take him over my knee right now. Punishment should happen swiftly and surely. Lydsay agreed. I guess I was squirming around too much as she put my head in a headlock between her thighs. Sara really seemed to enjoy spanking me and teasing me. When she was through she cupped my balls in her hand "my tits are off limits to you until and unless I decide otherwise. Agreed?"

I nodded my head in agreement.

Say yes Ms. Sara I am sorry for having offended you.

I did.

When we got back to Lydsay's I was sent to take a shower and get into my nightgown. I had a white nylon Baby Doll and when I joined the women on the deck Lauren remarked that I looked virginal. Lydsay said yes Tina and I are restoring his virginity to him. , Unless you count a dildo up the ass as sex. Sara said it is hard to find a good asshole to Dildo. Lydsay said "well I'm saving the first time for Tina after all he is hers." Well I still want to wax his asshole but I'm too tired remarked Lauren.

I'm not too tired Sara announced. Well if you want go ahead. So Sara brought me inside and did it on the floor of the kitchen because it was close to the microwave used to heat the wax. It was a very painful experience. Sara used her strength to hold me in place. After she finished she put on a pair of gloves and used her fingers to explore me. We returned to the deck and Lauren and Lydsay complimented me on my new look. If Tina said it was OK she was going to get a large dildo just for me Lauren remarked.


"Who is the little slut now?" She asked. One of my sins against her years ago was calling her a slut in front of new boy friends of hers.

Lydsay said "Oh by the way I've given the keys to the chastity to Lauren to hold so don't think once I go to sleep you'll be able to find them and get out of it."

Now spend some time kissing Ms Sara feet before we go off to bed. Sara actually asked for a massage as she worked on her feet all day. In a while we returned upstairs after I agreed to mow the lawn first thing in the morning. Lydsay had me put on the new harness and dildo when we got upstairs. I bet you now you are probably as well hung as Tom. Too bad it's probably too late to entice Tina back into your arms.

She put a sleep mask over my eyes. "I'm going to have you eat me out first and then have a nice ride. I think if you get the pleasure of seeing me nude you might be distracted." She had me lie on my back on her bed. She mounted my face and guided me to her.

She tasted great and weighing only a hundred pounds or so she was not uncomfortable straddling me. She remarked that Tina was right that I had good oral skills. When she mounted the dildo she pretty much controlled the rhythm. By the sounds of the moans she made she seemed to really enjoy herself.

jimmysub
jimmysub
21 Followers
12