Furthering My Education

Well I had to go back to Community College to take some child development courses as my wife and her lover are planning on having a child together. This is part one of the adventure.

I really don't like this idea but what my wife says go. Her biological clock is ticking and she has been with the same lover, Mr. Steve for about 3 years. So Debbie is going to have a baby. My role as her hubette will involve childcare. So I'm taking a semester of childcare courses at a local community college. I'm the only male in the class and at age 32 am ten to twelve years older than all of my classmates.

Who walks into class the first day but Denise? Denise works at a Consignment shop where my household clothes are bought. Debbie being a well-paid executive can afford to keep me as a housekeeper. Since she decided to keep me emasculated she has me wear women's clothes around the house. Usually I wear rompers and short-alls occasionally I'll wear a maid's outfit but the regular clothes are more practical to be in.

Denise is kind of smugly arrogant but friendly towards me in a condescending way. I am dressed in public in nominally male clothes though anyone observing closely would notice I wear a camisole under my pink dress shirt. She'll do stuff like if we are all in the cafeteria leave me to buss everyone's tray from the table. All the girls know I have a chastity device and wear panties under my street clothes. She'll mention in front of the others how some nice outfits have come into the store and I should get my sweet little butt down there.

The age thing comes into play. The other girls being just out of high school seem to get a kick out of busting my chops. At times I think I'm paying for guys who hit on these young women and piss them off and make them uncomfortable. Part of the course work involves working at a campus day care center. Because young kids can be messy we have to wear smocks when we are there. Of course all the smocks are very femine looking. Since I'm a male they don't have me do diaper changes. Though I have no predilection for young children it is politically safe that I am never left alone with a child.

Since I don't have to do the diaper changes I am responsible for most of the clean up including bringing the smocks home to launder on a regular basis.

Debbie was really pleased that I had a friend to take the course with. She has met Denise at the store. Debbie even offered Denise an opportunity to "baby sit" me when she and Steve head out of town for the weekend. Because Denise works and has a boyfriend she was not able to take her up on the offer. I don't think I need a babysitter. Debbie feels that it is important to have someone around to keep his or her eye on me. I admit one time when they were gone away I rummaged around in Debbie's stuff looking for the second key to my chastity. It's fine for Debbie to be away fucking her brains out but it is like a big deal that I get jerk-off time once a week. Any way the key that isn't around her neck is tucked away in the safe deposit box.

Ever helpful Denise introduced Julie, another classmate, as a potential babysitter. Julie was like a cheerleader jock type in high school very snobbish. Though I admit with her long curly red hair and strong assertive personality she is very attractive. Julie was willing but wanted to still spend time with her boy friend. Now I am use to various women seeing me in drag and Steve and I get along all right but Debbie's sensitive to my shyness around real men.

So Julie can have Tom over after 8p.m. and he needs to leave early in the morning. As my babysitter she gets to determine my bedtime. My room is in the basement conveniently locate near the washer dryer. I even have my own computer. Though I can't have Internet access due to some problems with my surfing adult sites in the past.

Debbie really liked Julie. She encouraged her to start off strict with me and to lighten up and be sweet only when my obedience and devotion has been firmly established. I thought during the interview process that it was a bit of overkill to bring out the riding crop to start my respect lessons. Debbie hardly ever uses the crop on me anymore. She wanted to make sure Julie started off on the right foot by establishing her authority.

Not only was Julie enthusiastic about cropping me she told all the other girls in the class the next day. Boy did I get teased something fierce. Plus I had to explain the reason I needed a babysitter was so my wife could spend the weekend away with her manly stud boyfriend.

Julie also worked out this compensation deal where instead of money changing hands I would do house work and chores for Julie and her housemate. Don't let anyone tell you girls are neater than boys because it is not always the truth. Debbie must of told Julie about blue balling me. No sooner do we get to her place she starts changing right in front of me. From her school clothes into this halter and shorts outfit.

I'm staring and she is like don't stare at me. Cupping he firm young breasts in her hand she says I don't really think of you as a guy. I often change in front of my girlfriends. We are always trying on each other clothes. Debbie says I have to supervise your baths so we might as well get use to seeing each other in various stages of dress.

"Besides Debbie says I can give you a tip for helping around here. If you want to eat some pussey in a couple of hours you better get busy." So I went to work and got started on getting her place sparkling clean. Just before it was time to go home she had me eat her out. She explained that her boyfriend had worn a condom when he fucked her that morning and she had taken a shower keep in mind eight hours ago this was one well-fucked goddess hole. She complimented me on my housework as well as my oral skills. Promising me that when she babysat for me that weekend there would be plenty more of both.

Debbie was pleased to hear that Julie was happy with my performance. As a treat she let me do some foot kissing after I gave her a pedicure.

The rest of the week flew by. Friday after class I went home anticipating, yet anxious, about the weekend ahead. I put on my favorite pink romper and these killer sandals that showed off the hot pink pedicure I had given myself.

I put fresh sheets and a nice bouquet of flowers in the guest room as a welcoming touch to Julie. She and Debbie arrived around the same time. Julie arrived with a couple of loads of laundry that would keep me busy. Debbie asked Julie how she thought I was progressing in my course work. Julie was very positive and suggested that I'd be a regular Mary Poppins or maybe a real Mrs. Doubtfire.

Well that's good to know. Steve and I have decided to leave our birth control home for the weekend. Julie was really encouraging and complimenting Debbie when Steve came by. I carried Debbie's bag out to Steve's car. Steve nudged and winked at me about not putting the make on the babysitter. Debbie made a comment to Steve about not getting his hope up, as he would never be giving this babysitter a ride home.

Debbie had me wish the two of them good luck and many a happy fuck. She also told Julie that her report on my attitude and behavior would determine if my chastity came off for a little playtime. Julie volunteered that if I was the good little boy she expected she might even be willing to give me a hand job.

No sooner were they out of the driveway Julie was pumping me for information about Steve. Boy is he a hunk; I can really see why Debbie likes him. Did you see the way his hand was cupping her ass as they were leaving. Have you ever seen his prick? I bet it's huge. She convinced me it was just girl talk and that I was not violating any confidences.

"I'll undo my halter for a couple off hours if you don't clam up on me". I told her how when Debbie first brought him home she measured both of us. His prick was like twice the length of mine and 4" in circumference. So Debbie was getting it twice as good as I was ever able to do. I told her about his endurance and stamina. It was not unusual for me to hear them go at it for a couple of hours pause for a while and go at it again. I explained how Debbie had hooked up an intercom between our rooms so I could listen in. Before she had brought him home they had made tapes for me to listen too so I could get used to the idea of them having sex..

She asked if I still listen to them and explained not really as they left me totally blue balled. This was all she needed to hear as she had seen the stereo system in her room. She assured me that if I didn't tell Debbie she wouldn't. She really wanted to give me a good report. Though she intended to give me a good cropping it might ruin the mood to start the weekend with one. She made a motion with her hand as if she was jerking me off. Under her spell I got a couple of my favorite tapes. For foreplay she had me undo her sandals and lick and kiss her feet. As a special treat she had me undo her shorts with my hands and take her panties down with my mouth. By the time I was starting to lick her we were listening to Steve describe one of Debbie's professional quality blowjobs. I think Julie had her first orgasm as Debbie was describing how Steve's massive organ was about to penetrate her tight cunt.

The tape actually ran out before the two of them had gotten off. But Julie didn't seem to mind as she kept my head firmly between her thighs until she felt somewhat satiated. My romper was soaked in sweat when she finally let my head out. She gently used her feet to move me to the floor so we could both get a rest.

She was so full of goodwill towards me she actually let me shower with her. Since some of the girls from class were coming over with a pizza to hang out for a while she had me dress in my black slip and frilly apron for when I'm maid up.

Denise, Suzy, and Wendy came by bearing a pizza at about 8 or so. Julie had kept me busy doing a load of laundry. Though friendly she was business like giving me instruction on how she wanted her laundry done. She was kind of busy writing a paper for a class she had that I didn't. She commented that she didn't know how she was going to get it typed in time for class. I suggested since her boyfriend was coming over the next night it would give me something to do when I had to go to my room early.

The girls giggled and teased me as they enjoyed their pizza. Julie told them how what I lack in the prick department I more than made up with my tongue. I think Denise was regretting not taking the babysitting job. Debbie called to confirm that they had arrived at the Cape safely and were getting ready to rest and procreate. Julie assured her it was just the girls from the class and I would be safely out of the way when Tom came over the next night. "Nanny" even said she 'd type my paper for me when he came over. She's such a good hubette you must be so proud of her. Now relax and work on giving her a child to look after.

The other girls had a hard time not bursting out laughing while listening to the conversation. Denise once Julie was off the phone said Nanny? And through the laughter explained yea see it what his role is going to be and it's a girls name." That's my position and I'm sticking with it." The name has stuck since then. Even a couple of the professors will let it slip out when addressing me.

Suzy and Wendy left a little later promising to come by for a swim the next day in our pool. Denise hung out lingering. She suggested that Julie "owed her" for setting up the gig for her. Julie defensively said if I were getting any money I'd share it with you. Denise said it wasn't about money but in her years of sexual experience she had never been eaten out without having a cock in her mouth some where in the process. I would like to be eaten out without having to do anything in return. No problem Julie responded. Have you ever wanted to whip a guy?

Well I'm pissed at Dave tonight. He chose to go to a ball game instead of seeing me.

Julie said why don't you give nanny a whipping and then I'll bring him to his room to change and I'll leave the two of you alone unless you want me to stay.

I fetched the riding crop for Denise. She was still dressed in a blouse and longish skirt from work. Julie suggested she take off her blouse so she'd have a better wind up. Once it was off Julie said oh that bra looks so uncomfortable. Yea well I wear a minimizer or a lot of times every guy is like talking to my breast. I had taken off my slip apron and laid across the stool. Denise after being assisted with her bra removal by Julie paused. Actually nanny has been such a good little fellow maybe I should just take him across my knee.

Julie was like whatever. I said that I should probably lay a towel across her skirt because even in my chastity I can have pre cum discharges. Denise complimented me on my thoughtfulness. While Denise was giving me a spanking Julie slipped out of the room returning in this nylon sleeping gown. She sat in a chair opposite us and fondled her breasts.

Denise wound up my spanking by saying one down one to go looking at Julie. She was like what do you mean? Well I think a little red head should be spanked for teasing me like that. Like what?

Playing with those cute little breasts of yours is turning me on. Oh does cute little Denise have some Bi tendencies?

Aye you going to make something of it?

Well get over here and across my knee or you'll be sorry. Surprisingly Julie hopped right up and positioned herself across Denise's lap. Denise allowed me to pull up Julie's nightgown over her ass. I was then instructed to hold Julies feet to keep her from struggling, When Julie got up off of Denise's lap the towel was a lot damper than I made it. Denise used it to smear my face before having me kiss Julies cheeks to ease any pain.

I almost got sent to my room at that point. They had each other to play with and didn't need me. I explained that whenever Debbie disciplined me she would have me do some serious ass kissing to show there was no hard feeling.

It was remarked that my boy prick didn't seem capable of hard feelings. Denise really took control of both of us at this point. She had Julie watch as I undid her skirt and did the panty removal with my tongue. She positioned Julie in the same kneeling position I had been in earlier. With just a piece of saran wrap between my mouth and Julie's asshole I rested my head on Julie's feet as her asshole was positioned. It seemed to work out ok. Julie ate Denise while I made love to her asshole with my tongue. I was kind of disappointed a half hour later when I was sent to my room so they could have private time together.

I was so blue balled and frustrated I tossed and turned most of the night. Up early I listened for sounds of stirrings from the guest room before knocking. I have this routine when Debbie and Steve spend the night to bring coffee to them in bed and to get their breakfast order. I heard them talking and giggling and knocked on the door. I heard Julie say who's there? Jimmy I replied.

Jimmy who is jimmy ' what happened to nanny?

I replied I mean nanny. I was granted permission to enter. Denise streaked past me to make a toilet run. I looked at Julie who seemed to be glowing from being party to a ravishing. I stood there in my blue baby doll absorbing the smell of sex. Well nanny what is it?

I was wondering if you guys wanted me to bring some coffee up. Denise came back and gave me permission to so. I was allowed to sit on the floor as they explained that if word got out about what happened here I would receive a series of serious whippings that would keep me from sitting for a good long time. I promised my discretion.

The two of them showered together as I started breakfast preparation. We were all friendly and warm towards each other. I mentioned that I was disappointed that I had not gotten to actually eat Denise out. I explained that often when Steve and Debbie would be having breakfast I would position myself under the table and do any clean up that Debbie might need.

Because I was being such a good sport Denise granted me permission to have her for breakfast. Their conversation was about whether what happened was a one time thing or not. They casually agreed to see how things worked out.

Julie explained how are day would involve spending the morning doing some more cleaning at her apartment followed by an afternoon of pool time. Denise had to go to work but said if it turned out to be slow she'd close up early. Not many more days left to sunbathe might as well grab them while she had the chance. She also suggested that we stop by at the shop on our way back to the house. She also asked if she could bring a load of laundry by with her. Julie was like of course. Nanny will be going to her room early tonight might as well keep her busy. God knows she should get use to doing laundry when Debbie has her child she will be kept plenty busy.

Denise as a special treat picked out a pair of Capri slacks and a top that went with it. Too bad she's so flat chested but I'm so big I can never wear anything with spaghetti straps. Julie called her roommate Chris and confirmed the apartment was a male free zone before brining me over there. Julie introduced me as nanny. Chris chuckled at the reasoning behind it. I had a couple of hours of chores to do. Julie took a nap. For some reason she was tired. Chris supervised me. Even sharing with me that now that I was around it would be nice because as many roommates they had conflicts around cleaning they now had maid service.

Chris admired my pedicure and was pleased that I was able to give her one. She had to go to work and could not come to the pool party. She did have me kiss and massage her feet to show my gratitude for being allowed to serve her.

Stopping by at the consignment shop was cool. It was actually pretty dead in there. I found a couple of leotards to exercise in and was shown some Maternity clothes that Debbie might like. Julie actually picked out this sexy nighty that was a bit big for her but she would wear it that night and leave it for me as a souvenir.

Denise reported that her boyfriend had left 3 or 4 messages on her answering machine. She had talked to him and found he was all worried and contrite. He had agreed to take her to a nice restaurant to make it up to her. Julie remarked that she should really put the screws to him.

Maybe I will. While I like nanny I don't know if I want one of my own. Though if he expects to continue to see me he is going to have to understand I'm the boss. She said she be coming by in a little while. I reminded her not to forget her laundry and offered to give her a pedicure for her date.

We returned home and I got the solar pool cover off as Wendy and Suzy came by. Julie declared the pool area a topless zone. I showed them the call button and put the electronic collar on before going off to do some chores. No sooner was I changing the sheets on Julie's bed than I was summoned. It turned out to be just a test to see how quickly I'd respond.

Though when Denise came along I was summoned to give her pedicure and just hang poolside to serve. I spent the rest of the afternoon in my panties except was allowed to wear an apron when cooking burgers and dogs. They got a kick out of the kneepads I wear when I kneel on the cement apron of the pool.

The conversation was how Denise should make Dave squirm and to start Domming him from they're on in. Wendy said stop him at 2 beers so his performance isn't impaired. Make him open and close doors for you. If you meet up with his friends, do a little flirting. Have him kneel to apologize and only accept it when he kisses your feet. Give him a little foot job when he's done eating you out. None of these comments were mine.