Chapter 4 The Training Begins I’m led up the stairs and she pauses at the bathroom, telling me she needs to freshen up. She suggests I go turn down the bed and light the candles she set out. It seems like a good way to kick off the evening’s events. Sitting on the edge of the bed when she enters, still wearing her teddy. “Glen, Honey, why don’t you brush your teeth and get all freshened up for me? Oh, dab on some of that cologne I left on the counter; I just love how it smells.” “Ok, Sweetie.” I dutifully head down to the bathroom. I needed to take a piss anyway, and my teeth did need brushing. It seemed like a normal request. As for the cologne, we’ll see. First, I pee and put some paper in the hole, wash my hands and face, brush my teeth—damn it’s still no comb—and then brush my hair. I decide to pull out the paper, figuring enough time has passed for everything to drain. Rewash my hands. Now for the cologne; the bottle doesn’t have a name on it, looks like it was rebottled, which is strange. I take a sniff; it doesn’t smell bad, so I dab some on. Actually smells pretty good. Rewash my hands again to get excess cologne off. Look myself over in the mirror; looks okay except for this stupid nightgown. I enter the bedroom and close the door—it doesn’t have a lock now, though I thought it did two years ago—oh well, maybe not. She is already in bed with only candles lighting the room. Soft instrumental music plays; it’s a love song I recognize but without vocals. “Honey, take that silly nightgown off and get into bed.” I quickly remove the horrid gown and climb into the right side of the double bed. She turns to me and says this is going to be a long night, hopefully very satisfying. Lying on our sides, we start kissing; our tongues battle it out to see who is superior and can dive deeper. She must have removed her teddy as I feel the soft bare skin of her back with my left hand while my right arm is pinned under me. I slowly move my left hand between us and palm her soft, luscious breast. As I start a rhythmic massage keeping time with the music, she begins to moan. We continue for the next few minutes as she keeps up her moaning and mewling. I, on the other hand, while enjoying her kisses and feeling her boob, am fighting off getting too hard. The pain seems under control as my body fights an erection that is constantly distracting me. This thing is turning into a type of torture device playing with my mind. She shifts positions and rolls onto her back; I follow suit and roll on top. She pushes my head down. I think I know where she’s leading and kiss her neck and chest as I make my way to her sumptuous breasts. As I suck her left breast, softly massaging the other with my mouth, her breathing deepens. “Oh, honey, yes keep that up.” After a couple of minutes, I decide her other breast is being neglected and switch sides. My left hand is now free; she takes it and places it between her legs, telling me to rub until my hand is soaked. I wasn’t quite sure what ‘soaked’ meant—maybe she knows how to get out from under this cage and wants to be well lubricated. So I start rubbing. She’s completely shaved and smooth now, unlike two years ago. It feels nice, although some hair can feel wonderful too. I stick my finger in; she says not yet, keep rubbing higher. Her clit starts getting bigger and longer, so I decide to rub there and pinch it softly between my fingers. Now I have no idea what I’m doing. I’ve rubbed pussies before, but only until they get wet for entry, never this long. Yet she seems to be enjoying it. She is getting drenched along with my hand. Then she takes both her hands and pushes against the top of my head, saying “lower.” What does that mean? She keeps pushing my head down, so I start kissing and licking her stomach. She says lower again; now I’m at her belly button and waistline. Lower still. At this point, I object. Then she shoves my head down further. “Glen, I need you to start licking me.” “Jan, Sweetie, I can’t… I mean that’s where you pee from and everything else a woman does.” “Honey,” she says in her softest sweet voice. “You guys think it’s perfectly acceptable to suck you off with our mouth, take your spunk, swallow it, but you can’t even lick my pussy? Honey, I need this right now. Mom says it will put me into orbit. So please just start… NOW!” Crap, what am I going to do? If nothing else, the thought of this got me soft. I start licking; hell, this isn’t too bad. She tastes fairly nice, and her smell is becoming quite pleasant. Why are my legs getting hard again? The pain starts up as well. I keep licking and decide to suck her clit into my mouth giving it a few soft nibbles. This seems to put her over the edge; she starts bucking and screaming. Oh hell, what have I done! I stop. She screams not to stop, to keep going. So I start up again, having a hard time maintaining contact while she bounces and gyrates. It goes on for what seemed like an eternity but was likely only a minute or so. Then she settles down taking long labored breaths. I lay there with my head between her legs wondering just now happened; I’ve never seen a girl do anything quite like that before. “Oh, Honey, that was terrific! I didn’t know an orgasm could feel so good.” “You had an orgasm?” “God yes Glen, it was much better than anything you did to me before. Start licking again; I want to see if I can have more of these.” I start licking again. It’s only a couple of minutes and she starts panting. I decide to try fitting my finger in her again, pushing my middle finger up into her soft velvety fold—god she feels great—and moving it in and out while pressing against her insides. Working on her clit again, the bucking and screaming start anew as I keep pumping my finger and sucking her clit all the while trying to keep my mouth positioned. Her legs wrap around my head squeezing me so I can’t lose contact. It was still hard with all the thrashing; this time it lasted twice as long before she settled down. After a short period with her legs still clenched around my head, she says: “Start again, don’t stop until I tell you to.” So up I started again. This time I managed three fingers in and the bucking just kept going; she would settle for a few seconds then start up again. I just kept licking, sucking, and fingering her. My right hand was free so I reached up playing with her breasts squeezing and pinching her tits. She screamed: “Oh god yes, don’t stop Glen! Oh my god!” My neck started getting sore after an hour of this. I think she came ten to twelve times; I lost track through it all until she told me to stop releasing my head. “I… think… I’ve had… enough… for now,” she says between breaths. I lay there a couple of minutes before moving back up face-to-face. “Glen, don’t kiss me.” “Uh what do you mean?” “You need to wash your mouth out and brush your teeth first.” “Why?” “Because I’m not going to taste myself; that’s just gross.” “But you said…” “Doesn’t matter! Just go get your face and mouth cleaned up, use some mouthwash—it’s in the cabinet.” I get up quickly walking naked to the bathroom hoping her mom doesn’t walk down the hallway. What the hell just happened? I guess she had the time of her life orgasm after orgasm. Now I’m starting to feel used. What about me? How am I supposed to get off with this damn lock on? She won’t let me kiss her until I wash my mouth out, so I wash my face brush my teeth and use the mouthwash.
I make my way back down the hall and get into bed.
“Oh, honey, that smells much better.” Then she starts kissing me. Her hands reach down and begin squeezing my butt. I manage to slip one hand between us and start working on her breast while moving my other hand over to her ass. I push my fingers between her legs and start fingering her pussy. She begins moaning again—do I want to continue? I ask myself. She breaks our kiss, saying that feels good; just keep it up but go really slow. I guess that answered my question.
She lifts a leg over mine, giving me better access, so I slip in a second and then a third finger. Now she starts panting again, pressing her mouth harder against mine. Her tongue moves at a rapid pace, her breathing gets shallow and fast, and then comes the bucking. Not sure why exactly, but I decide to speed up my strokes—it just seemed like the right thing to do.
She hits her plateau and starts coming down. I stop fingering her but keep them inside for now. After a few minutes, she rolls onto her back, which forces my hand out.
“Oh Glen, that was incredible, but I’m exhausted now; I think I need to go to sleep.” She turns over with her back to me. “Glen Honey, why don’t you scoot up behind me and hold me?” Well, I’m not passing up the invitation. I quickly spoon her and cup her breast. Now my cage is pressed up against her ass, and after a couple of minutes, she says it’s bothering her and we need to figure something out.
“Glen, I want you to hold me, but that metal is poking me all wrong. I need to find something to put over it.” She gets up, turns on the low light by her nightstand, and heads to the dresser. She comes back and tells me to put these on, handing me PANTIES.
“Jan, I can’t wear your panties.”
“You sure you can! I accidentally bought a package of these that were too large. The store wouldn’t take them back once opened, so I just kept them in the back corner of the drawer. They should fit you. I really want to feel your bare skin against me, but the metal hurts me.”
I get up and put them on; they are still a tight fit, and I’m hoping they don’t dig into my waist. In the dim light, it looks like they have a floral print. We climb back into bed and spoon again.
“Oh, that feels much better. Thank you, Honey.” Five minutes later, I hear long, soft breaths; she’s asleep. I lay there for half an hour, wondering what just happened—frustrated and in desperate need to cum. I wake up in agony; my balls feel like they are on fire and being ripped off. I quickly roll out of bed.
“Glen, what’s the matter?”
“My balls really hurt. I need to go try to pee. Frank said this could happen and that’s exactly what I needed to do.”
“Okay then, go down to the bathroom.”
I hobble down the hallway, pull down the PANTIES, and sit on the toilet, trying to relax and piss. Slowly, I start to dribble, then a stream forms; the pain starts to lessen. After a couple of minutes, I’m starting to feel okay. I wipe myself off and stand up—oh shit, I’m dripping! Grabbed a piece of tissue and stuck it in, pulled up my PANTIES. Now I see they have a pink and red floral pattern. God, I am not that kind of person; I like men’s clothes, not women’s.
When I return, she’s lying on her back asleep. I look at the clock on her nightstand: 4:20. I quietly slip back into bed and fall asleep. I wake up to a woman kissing me.
“Glen Honey, it’s time to wake up; I want to have some more fun.”
I’m groggy and glassy-eyed. Where am I? Oh, it’s Janet in her bed—and it comes back in a flash.
“What did you say, Sweetie?”
“I want to have some more fun. Last night felt like nothing I’ve felt before, and I want some more so I won’t forget the feeling.”
“Okay, Sweetie.” She starts dueling with my tongue and grabs my panty-covered ass. I cup her breast and move my hand between her legs; then she pushes my head down. I know the routine now: suck on her tits and rub her pussy for a while, then she pushes my head down again. I oblige. She smells and tastes different this morning—more musky, not quite as pleasant but not horrible. I decide to just go with it and start licking and sucking. I get three fingers in her again, and she starts bucking and screaming. I know her mother has to be hearing all of this; breakfast is going to be embarrassing.
She gets off me three times and makes me stop. “Honey, I think that will do it for now. Maybe we can do some more later on today. It’s 7:30; mom will be getting up soon and making breakfast.”
She sits up on the edge of the bed.
“Glen, I need to explain a few things about Mom before we get up, okay?”
“Sure.”
“Well, as you know, my dad was killed by a drunk driver 5 years ago. My mom fell apart and for weeks, she would get up without putting anything on—I mean totally nude at most, maybe just a pair of panties. If someone came over, she’d throw on a robe. She walked around the house all day like that. I don’t know why, but on weekends and after school, I started doing the same too. It has now become normal for us; we enjoy being nudists. What I’m saying is, she may not have anything on. Don’t take it the wrong way—that’s just how we are now. Also, she hasn’t dated either, and I know she’s pent up sexually. That’s why she did that last night. I think it really helped her. I don’t mind her kissing you as long as it doesn’t go too far. After all, the keys are locked away. Just let her try to have a little fun, okay.”
“So you’re saying you want to share me with her?”
“Not completely; just enough to help her get her confidence back. Then maybe she’ll start dating again.”
Now, her mom did look great—5’6”, about 125 lbs., boobs a little bigger than Jan’s and a great ass. I could see a lot of Jan in her. I didn’t mind her kissing me last night; it just felt uncomfortable.
“You don’t mind helping her out, do you, Honey?”
“If that’s what you want, I’ll try to accommodate her.”
“Great! I need to pee and take a shower; I feel all sweaty and sticky. You want to join me?”
We walked out the bedroom door just as her mom came out of hers. She was wearing panties—nothing else. I just gulped; she had to be at least a D cup, didn’t have much sag either. God, she is gorgeous.
“Hello you two. It sounded like you made my daughter quite happy last night and this morning, young man.”
“I hope so, Ma’am.”
“Well good, that is your job. Oh, I like the panties; they seem to suit you nicely.”
I could feel the heat in my face; I had to be turning a bright red.
“I’ll have breakfast made in about an hour, so take your time.” Then she walks by us and down the steps. That was just weird.
We head into the bathroom. She starts brushing her teeth, so I do the same. “Honey, could you turn the shower on and get it hot? Then step in so I can pee. I’m not comfortable having you watch me go to the bathroom yet.”
“Okay, Sweetie.” I take off MY PANTIES and step in, closing the shower curtain. Well, I might as well pee now and let it go down the drain, so I do. I’m thinking her mom said that was my job? I guess it did say that in the agreement, but what about me? I’m horny as hell and can’t get off.
“Move over, Honey, so I can get in.”
“Honey, can you wash my back?” “Sure,” I say. As she turns her back to me, I grab the soap and soap up her neck, back, and nice round ass. While washing between her ass cheeks, I decide to see what would happen if I stuck my finger up her asshole.
“Glen, what are you doing?”
I stop with my finger just past my first knuckle in her.
“I thought this might feel good.”
“I don’t know; just take it slow, and I’ll see.” So I start to move my finger around slowly while going deeper. Finally, I get my finger in all the way and start stroking her. Then with my other hand, I start rubbing her clit. She starts moaning; I continue while speeding things up. She starts shaking and panting; I just keep it up. I lightly squeeze her clit while ramming my finger into her ass. She explodes, yelling and shaking. Finally, she settles down and collapses to the bottom of the tub, sitting there p
Anting. She sits with the shower steam rising around us while I stand above her, my cage hanging over her head.
“Are you okay?”
“I’m not sure; that was unbelievable. I need to sit for a bit to regain my strength, alright.” A couple of minutes pass, and she extends her hand for me to help her up.
“I think I should finish washing myself. I don’t feel like handling you touching me right now. Glen, why don’t you wash yourself off and dry out while I’m finishing? Okay?”
“Okay, Sweetie.” I quickly rinse my cage; it didn’t need much cleaning since I had just showered ten hours earlier. Stepping out and drying myself, I grab the blow dryer to start the process. Jan walks out and asks what I am doing. I explain that it is the best way to dry off completely. She finishes drying herself as well.
I offered her some lotion around the ring, but she declined, saying we need to finish before breakfast gets cold. Well, I decide to put my panties back on because I’m not ready to run around their house with nothing showing except this cage. Jan says she will get me a clean pair and tells me not to reuse dirty ones.
We head to her bedroom. She hands me another pair of nylon stretch panties; these feature a light-to-dark blue floral print.
“Glen, you don’t have to wear anything if you want. I’m not,” she says.
“I’m not ready to parade around your mom naked yet.”
“Okay, you can always wear the nightgown then.”
“No, that thing looks horrible on me. Panties look weird, but at least they aren’t horrible.”
“Okay, Honey; it’s your decision.”
I put the panties on.
We walk into the kitchen holding hands.
She grabs three towels from the end of the counter and carries them to the dining room, placing them on the chairs. The dining table has its center leaf removed now, making it a short oval shape with four chairs around it. The other two chairs are pushed up against the far wall.
“Janet, what are all those towels for?”
“Since we are naked, we need the towels so our body secretions don’t get on the fabric. It is more hygienic,” she explains.
“Glen, how do you like your eggs?”
“Over medium, Mrs. Watson.”
“Okay, breakfast will be ready as soon as the eggs are done.”
A few minutes later, we sit at the table with Jan between me and her mom. I face her mother across the short width of the table. I couldn’t help but look at those breasts of hers; man, they looked great.
As we eat, her mom starts up the conversation again.
“It is obvious that you now know how to satisfy my daughter. With all the moaning and screaming I heard last night and this morning… Jan, did he satisfy your sexual needs?”
“Oh, Mom, did he ever! I never knew something could feel so good. His tongue worked wonders for me; nothing like what happened before.”
“Well Glen, it seems you’re not very strong with your cock, but you have found your calling with that silver tongue of yours. Glen, let me tell you the house rules so you know what to expect here. First of all, since you are not just an occasional date for Jan but her steady boyfriend who she is sleeping with, I don’t intend on changing my lifestyle or how I dress around the house. I am sure that Jan has explained to you that we both go nude most of the time around here. I’m not going to change that, and obviously Jan isn’t either, seeing as how she is naked right now.
You can wear anything you want or nothing at all; it doesn’t matter to me regarding your Fidelity Enforcer. I never told Jan exactly how I got this idea to go nude. She was too young to be reading erotic stories back then, but she’s eighteen now. So, I’ll tell you both: I read a story by Karen Wagner called Naked in School, and then several other similar ones. Basically, it involved a high school district project where one boy and one girl would be picked once a week to remain naked for all classes and school activities during that week. They were allowed—and even encouraged—to stay nude all week, including shopping or going to restaurants, but they weren’t required to; the requirement was just for school and related activities. The stories really captivated me.
After Jeff died, I fell apart, and getting dressed in the morning simply didn’t happen anymore. Then I started liking the feeling of being nude and free. Between those stories lingering in my mind and my depression, this is what happened. Jan tried to help out; keep in mind she was only thirteen then—and decided to support me by going nude as well.
Now it has become a routine that we both enjoy. Does that sound about right, baby?”
“Yeah, pretty much. But about the stories—I’ve never heard of such a thing as being naked at school; that would be just bizarre.”
“Look them up on the internet; it was interesting reading. With the go-nude rides appearing now on subways, trains, and buses in your underwear days here in New York, Paris, Japan, and elsewhere, I could see something like that happening too. Also, a high court in Maine ruled that a transgendered boy who identifies as a girl must be allowed to use the girls’ restrooms, gym lockers, and showers. California passed a law allowing any student from kindergarten through 12th grade access to whichever restrooms, locker rooms, and showers correspond with their identity, and they can play school sports with the opposite sex too. All that person has to do is say they feel more like they should be the other sex.
In New York, the court ruled that since men can go topless, women have the same right and may go topless in public without being cited. So I could see a place like San Francisco doing that within 10 to 20 years. Who knows what comes next?
Well, back to the rules: everyone dresses or doesn’t as they feel. Since you are staying here on weekends and eating here, I expect you to help out with household duties—mainly dishes and kitchen cleanup, plus occasionally other chores around the house. This is not a free ride; you are not just a guest but part of the family.
On weekends, you can stay as long as Jan wants you to. But on work nights or school nights, I expect you to go home at a decent hour—10 PM at the latest. If homework needs doing, then much earlier than that. Lastly, I don’t mind you looking over my body once in a while; it’s natural for a young man to look, just don’t keep staring at me.
Now, do you have any questions?”
“Well, a couple. You say I can spend the weekends here but not weeknights. Why is that?”
“I’m not having you move in permanently. If you stayed most nights or every night, that would be moving in. That’s not happening; I still need my privacy and solitude. No more discussion on this matter. Next question.”
“Um, well… this cage on me keeps me from even touching myself or letting me get off. I’m starting to get real pent up. How am I supposed to get relief?”
“That is the big question, isn’t it? And the short answer is: you don’t.” My heart started to sink as reality set in.
“Here’s the deal: I have one key stored in my safe deposit box at the bank, and it will be used only for a medical emergency. One other situation would apply if you are required to go through a security metal detector. If you give me enough notice, I will swap out your metal device with an all-plastic one for the day and switch you back as soon as possible afterward. If I don’t have enough notice, you will have to explain to the security officer that your girlfriend’s mother requires you to wear this.
I’m sorry, but that is just how it is. The other key is in my floor safe which has a time lock on it and cannot be opened for another 13 days. So you will have to tough it out until then. You will find that after two weeks of denial—and after enough stimulation—you will experience the best orgasm of your life. After a while, you will start looking forward to that 14-day release. It gets better after a few months.
Any more questions?”
“No, I think that’s it,” I say, holding my head in my hands like I have just lost everything in my life.
“Glen, think of it this way: If you hadn’t agreed to the terms in the contract, then you wouldn’t be here. You wouldn’t have slept with Janet. You definitely wouldn’t be standing there looking at me completely naked. I wouldn’t have kissed you last night. And you wouldn’t have a girlfriend.”,
“Instead of going out, you’d be at home, hoping someone asks you. I think that’s a reasonable compromise.’ “I suppose that is one way to see it.’ ‘So what are your plans for today?’ ‘I’m not sure, Mom. We haven’t talked about it yet.’ ‘Why don’t you two stay here then? It’s supposed to be warm and the pool is heated, so you could go swimming later on before hopping into the Jacuzzi. “What do you think, Honey? Sounds good? We could play Mario Kart on the Wii or maybe some other games.” My head was spinning and I just said, “Okay, sounds fine to me. I love Mario Kart and I’ll beat the pants off you—oh wait, they’re already off.’ ‘Well, you two need to tidy up here. I need to go freshen up.’ “Mrs. Watson, given the way you look and smell right now, I can’t imagine any reason why you have to. You seem very fresh to me. “That’s sweet of you, but use that charm on Janet, okay.” “Why don’t you just call me Joyce from now on?” “Yes, Ma’am… err, Joyce.’ “Ma’am works too; it depends on what feels most appropriate at the time.” She gets up and heads upstairs. “That was nice of you to say that. She needs to hear it from a man. Well, let’s get some aprons on for the dishes.” She leads me into the large pantry and grabs two aprons. I just stare at her while she wears one with nothing else underneath. She turns away, and I see her backside—goodness, she has a great ass. We return to the dining room, pick everything up, rinse them off, and put them in the dishwasher. “Glen, why don’t you finish the dishes while I set up the Wii?” “Oh, okay.” She kisses me, removes her apron, and heads to the living room. Well, guess I get to clean the kitchen again. I cleaned the pans and griddle, put them away, wiped down the counter and stove, and cleared out the sinks. There is a container of antibacterial wipes at the end of the counter. So I grab one and wipe down the countertops and stove with it. Now, I’m not overly clean by any means, but in the kitchen, I am kind of a germaphobe. I don’t mind other rooms being messy as long as they don’t involve old moldy food or look like something from a hoarder’s show. But where my food is prepared must be clean. I remove my apron and hang both back up before heading into the living room. The women are getting in some practice to get one over on me, I guess. I noticed Joyce was now nude; her legs were spread slightly, and she had been shaved except for a small patch just above her lips. I sat down between them and grabbed a controller. We played for about an hour and a half. They were good players and would gang up on me. They didn’t care which of the two beat me as long as I wasn’t the winner. That worked out about half the time, though I am pretty skilled at this game. It was around 11:30 when we put the game away and decided to go swimming. I still had my panties on; they kept everything pulled up nicely and prevented my balls from rubbing against my legs with the material between them. As everyone else got into the water, I realized I needed to ditch mine since they were naked. So off they came, and in went I for a swim. The three of us had a blast taking turns climbing onto my shoulders while I walked around the pool playing catch with a beach ball. Bare pussy against my neck felt great, with two women vying for my attention. We played keep-away, and I got to kiss and fondle whoever I caught. It seemed Joyce let me catch her often. Her tits felt wonderful. After an hour of this, they decided it was time for lunch. Joyce said a gentleman would wait until he dried off before helping the women dry first. So I grabbed a towel, dried them off, and then myself. If being treated like a gentleman is what this involves, I think I could get used to it. The women made sandwiches and laid out some chips. Joyce pulled clam dip and bean dip from the fridge. We took everything onto paper plates out to the patio; cleanup will be easy. “Glen, are you having fun with us girls giving you all this affection?” “This has been the best weekend of my life; I’ve had so much fun. Though I am a little embarrassed.” “Why’s that, Glen?” “Well, I’m Janet’s boyfriend, and you’re her mother. It feels a bit awkward doing all these things with you while she watches. “Glen, Honey, Mom and I discussed this earlier while you were washing dishes, and I felt it would be good for both of us since you seem to care about her so much now.” “Mom has helped me think about dating again?” “I was reluctant at first, but now I can see how it is helping. I feel more like a woman again. Glen, I really appreciate what you’re doing for both of us. This wouldn’t have been possible without the device.” “Joyce, I’m willing to help as long as Jan doesn’t object or later changes her mind and gets mad at me. “Honey, that won’t happen. If anyone gets angry with me, it will be Mom for going beyond what I approve of.” “What have you approved?” “Kissing, fondling, body rubs—but that’s all. And I come first; if I want you to myself, you are mine, period. Speaking of body rubs, do you think you could give us both a massage?” We went back inside and up to Joyce’s bedroom. Her room was huge, at least 25 by 30 feet. The bathroom had a large double sink, a spacious tiled shower that easily fit three people with dual heads and one rain head in the center, plus a large corner tub made for two. The walls were soft green with white trim and a sliding door to the balcony overlooking the pool and backyard. From there you could see into the neighbor’s yard where a family was playing in their pool. Her closet was massive, almost the size of a small bedroom. She pulled out a folding massage table and set it up. “I need to pee; why don’t you two do the same before we start?” Then she headed for the bathroom and closed the door. We walked down the hallway into the bathroom. Jan just sat down, peed, wiped herself off, and stood up. “Your turn.” I couldn’t believe it—a girl was peeing right in front of me without seeming to think anything of it. I sat down and tried to pee but struggled with her standing there. She turned on the sink faucet and started washing her hands. The sound of running water helped, and I finally got going. After finishing, I wiped off the cage and placed some paper inside. We headed back to Joyce’s room and heard the shower running. “Mom, are you in there?” “Come on in; we need to wash off the chlorine from the pool before applying lotion.” We stepped into the shower, and Joyce handed me a bottle of body wash, telling me to wash her up. Oh dear, I started at her neck and back, moved down to her butt cheeks and crack between them. She turned around and said it was time for the front again. This time I started at her neck working downward, spending too much time on her breasts before continuing lower. I hesitated at her pussy. “Come on now,” she said; that’s where I need cleaning the most because chlorine will irritate me later.” So I began washing, making sure to get between her lips, and once again spent extra time there as she started panting. “Okay you two, that’s enough of that. You’re going beyond just cleaning now.’ “You’d better stop, Glen,” Jan said. “She’s right; could you do my legs though?” She spread her legs apart, forcing me to kneel so I was looking directly at her pussy. I tried to hurry with her legs while she kept taking slow, deep breaths. Once finished, I stood up. “Okay Sweetie, your turn.” Again, I started with Jan’s neck and back before moving to her butt; I thoroughly washed the crack between her cheeks and slipped my finger in slightly. “Oh god Glen, not here in front of Mom!” I stopped and pulled my finger out. She turned around, and I moved to her front, spending a lot of time on her breasts which I bent down and began sucking on. “Stop it, Glen; mom is watching us.” I paused again and continued downward. When reaching her pussy, I washed
r till her clit get engorged and she not thinking well. Then I slip a finger in her. I guess that’s when she comes back to reality and sternly tells me to stop it. So I do. “Now get on your knees and wash my legs.” I willingly comply with her pussy staring me in the face. As I start to wash her legs I move my head closer to her and try and lick her. “Glen save that for later and just finish up.” Again I comply like an obedient servant. Then they decided to both wash me. With my ass and balls getting a double washing. I don’t know why but I’m not getting as hard or hard as often. I would start to get an erection, start to feel pain, then soften again. I guess my body is adjusting. We all finished up rinsing off, we had all three heads spraying us with hot water. I thought this is great. As we step out the girls grab towels and wrap their hair in it setting on top of their heads. Then Joyce hands me a towel. “Ok Glen, dry us off. “Yes Ma’am.” I like a good gentleman and servant dry both of them off. I know it’s a terrible job, but someone has to do it. I finish drying off and Joyce grabs the hair dryer and tells me to go and get the other one in the hall bathroom for Jan. Now I really do feel like a servant. I comply and get it for them. I still need to dry my cage off and wait. Joyce finishes first and I ask for the dryer. Now my hair is short and dries in five minutes and don’t use a dryer on the hair on my big head that is. The other hair I guess I do use a dryer on now. I start to dry everything off and Janet says “Looks like your getting this all figured out. Are you going to need some lube or lotion.” I think, she knows about using lube on this thing, what else does she know about. “Yes I’ve been using hand lotion.” “Ok there some in the medicine cabinet.” I finish, grab some lotion and put some on. I notice the paper in the cage was gone, I had forgotten about it till now, must have went down the drain. I walk into the bedroom Janet is laying on her stomach with a bottle of stuff marked warm sensual body lotion for lovers. I think ok this is going to be interesting and I start massaging her neck and back, I decide I probably should spend a lot of time on her back, she keeps on moaning and purring, I start rubbing her ass cheeks and firmly squeeze and massage her there for a good 5 minutes, Then I start on her upper legs. She spreads her legs a little to give me more access. I start on her left leg and work down to her foot and then rub her foot for several minutes letting the lotion soak in. Then I start on her right foot and move up to between her legs. She has me stop and rolls over. Ok you can continue now, I start at her neck and work down to her breasts. Now her mom is watching all this and I’m getting really embarrassed. “Honey, why is your face turning red.” “Well I’m massaging your boobs with your mom watching it is a little embarrassing.” “Well I’m going to be watching you do the same thing to her. So you might as well get over it. Now keep rubbing in that lotion. It feels so good and it gets nice and warm as you rub it in.” I continue with the massage and try not to think about the situation. My face starts to cool off. I work my way to her pussy and start rubbing the lotion on her upper thighs and then her pussy, she starts to moan and tells me to do her legs. I stop and do as she says. It takes another five minutes to finish her off at her feet. She sits up on the table and has me help her get off then gives me a nice deep kiss. “Thanks Glen that felt wonderful. Ok mom your turn.” I start the same way as I did Jan and work down to her ass. I rub her cheeks about ten minutes while running my hand under her and stroking her pussy lips. Then I know I have to continue with her legs as Janet keeps clearing her throat. I work down one side then up the other ending at her crotch. She turns over. Oh god does she have a body, I feel myself getting hard again and stretching out, Shit I hope Jan can’t see this. I try to clear my mind as I start on her upper chest, I know I have to go lower and massage those boobs of hers but keep hesitating. “Glen I need you to massage the rest of me, they’re just boobs.” I started on them and kept going for a long time there. I hear Jan clear her throat several times so I continued downward. Once I reached her pussy I decided to just go for it. I started to rub in the lotion all though her pussy and felt he clit start to engorge, I figured I would just continue until someone complained or until I got her off. After a couple of minutes she started panting, so I just kept at it since I had both my hands on her I slowly penetrated her with my finger and started to pump her faster and faster, then I squeezed her clit and she screamed and started thrashing about. I just kept it up. I looked up at Jan and she had this deer in the headlights look with her mouth gaped open. Oh shit I knew I was in trouble but at that point I couldn’t just stop. It lasted about a minute before she started to come down. I pulled my hands back applied some more lotion and started to quickly finish with her legs. I went down both legs at the same time trying to finish as quickly as possible and get the scolding over with. I figured I went way to far and was in big trouble. When I finished, she sat up and walked over to the bed and sat on the side of it. “Glen, I’m really sorry I let you go that far, once you started it felt so good and I just couldn’t stop you. It’s the first time in five years I had a man touch me like that. I apologize to you and Janet. Janet can you forgive me?” “I don’t know mom I didn’t think I would ever see my mom have an orgasm in front of me, especially with my boyfriend. But yes mom, I forgive you. You must of had a terrible time the last few years. I mean after last night, I don’t know how I could go more than a few days without an orgasm.” “Well I’m thinking I’m not in trouble.” “Glen you on the other hand knew what you were doing and should have never done all that. We will discuss this later and see how you can make it up to me.” “Well Glen I had planned on giving you a big kiss but I don’t think Jan would approve now.” “It’s ok, I’m going to my room. I’ll give you five minutes with him. Then he’s mine for the rest of the day. Glen you keep your hands and mouth above her waist, understand.” She walked out before I could answer. “Joyce, now what?” She patted the side of the bed and said to sit here. She put her arms around me and started kissing me. She laid back on the bed pulling me with her. We just kept kissing and for the whole five minutes and nothing else. Actually it was quite nice just kissing. Then she pulled away. “Thank you Glen, were not going to be able to continue this you know. I think it’s time I found someone my own age. Now go and take care of Janet. Sorry for getting you in trouble.” I just got up and walked out without saying anything and headed for the tongue lashing. “Glen close the door and sit over here on the bed.” Oh I was in trouble. “Glen you’re not in trouble, but I don’t want my mom to know that. Just before we go out I’m going to give you 20 swats on your butt to make you good and red. This isn’t to punish you, but to make mom feel really bad. Sorry you have to get the brunt of it, but that’s the breaks. Are you going to be ok with that?” I’m thinking 20 swats, I haven’t been spanked since I was five. Then mainly to get my attention. I guess it could be worse and she really isn’t blaming me which she should. “Yeah that’s ok.” “Now come over here I need some real love and attention.” I got her off five times, when she said she had enough. “Ok Honey, bend over the bed.” Now I’m thinking she’s going to use her hand. What I felt was a wide leather belt, and she swung hard. When she was done, I was hurting, I mean it hurt like hell.
at again. Now come here and give me a kiss to make up.” I stand up and we share a kiss for several minutes. Then she takes my hand, leading us downstairs into the living room. “Glen turn around and show mom what she caused.” I pivot. “Oh shit Janet, how could you do that to him? That looks pretty severe.” “Mom that’s your fault he got punished; next time don’t let it go that far.” “Oh Glen, I am so sorry. Can you forgive me?” Now my head is swimming: she’s being blamed while I get spanked. “Mom I grabbed some ointment. I think you should rub it in.” She tells me to lie down on the couch and starts rubbing the lotion onto my cheeks. My butt was burning, but the cool ointment made it feel a whole lot better. I figured it would be several days before I could sit for any length of time. As she works the ointment in, she explains how sorry she is to have gotten me punished for something she should have stopped earlier. I ask her if she can remove this cage from me. She says no, sorry. It was worth a try. When she’s done, she tells me my clothes are washed and folded up in the laundry room. “Glen it’s 4 pm. Have you called your mother at all this weekend?” “No, Ma’am. My phone has been in Jan’s room since last night and I haven’t checked it for messages or missed calls.” “Well I think you should call her. I’m sure she would like to hear from you and probably wants to see you some time this weekend. Maybe you should plan on making it a day trip and have dinner with your mom.” “I thought I was spending the night.” “Glen, I told you: on work nights and school nights you are not staying here. Remember?” “Yeeesss Ma’am.” “Joyce, I think the two of us need a break from Glen. So why don’t you two finish with each other so he can get dressed and go home for the evening?” “OK mom, come on Glen, let’s get your clothes and go up to my room.” We retrieve my things and head upstairs. She tells me she’s sorry about the whipping but had to convince Mom that she means business and won’t step over the line again. I think hell, I’m the one in pain; I still don’t get it. We kiss and neck for a while before she tells me to get dressed. I ask if she has any other panties my size in white. “Why?” “Well they keep everything pulled up just right. If I wear them then I can put my regular underwear over them, so I think it would work better.” “So you’re going to wear two sets of underwear? Why?” “In case they show above my waistline like when I bend over, then men’s underwear will be visible and not the women’s. I can’t have anyone know I’m wearing panties or this cage. “That makes sense. Well I have one pair, but I don’t know if they’ll fit you.” I try them on; they’re too tight. She grabs another pair like the ones I wore but with a purple floral pattern. I put those on and then my briefs over top to get dressed. Damn, my butt hurts. I checked my phone: three missed calls and a text message from my mom wondering if I was coming home. I called back saying I would be there in 30 minutes. We went downstairs and said our goodbyes; both gave me a big kiss and hug. I got in my car, thinking what a weekend it’s been and what the hell have I got myself into. I drive to Target and get two bottles of hand lotion. I decide to try the unscented aveeno because the lotion at Janet’s house does have a definite scent. On the way over I had thought about the panties: maybe speedos would work. I look for those and find a 3-pack for $14.95, which is outrageous at three bucks a pair. Oh well, I grab a pack. I pass by the women’s underwear section and take a peek. Now nervous being seen in that area, I glance quickly as I slowly walk past the shelves. Shit, here’s a pack like the ones I have on. A pack of 5 for $8.95. That sucks; us men are being ripped off. There isn’t much difference: same kind of material and amount of fabric, except maybe a smidgen more in the front for the pocket part. Come on, it’s almost three times as much per pair. I look for a hair dryer for the hall bathroom and find one for 20 bucks. This thing is starting to cost me money. I checkout and head home. What is my mother going to say about me sleeping over at Jan’s? I leave one bottle of lotion in the car for work. “Hi mom, I’m home. I’ll be in my room for a few minutes.” “Ok, but I need to talk to you.” I hurry up to my room; I don’t want to listen to the lecture just yet. I lock my door and try on the speedos. Well, they cover the cage nicely, fit around my balls like the panties do, hold the cage up, and feel a little more comfortable. I decide these count as men’s underwear so there’s no need to cover them with more layers. I get dressed. Now what to do with those panties? Stick them in the Target bag and put them at the back of my dresser drawer. I go pee before heading down for the inquisition. Ok, let’s get it over with. “So son, where have you been for the last two days?” “Mom, I’m eighteen and should be able to spend my time where I want.” “That doesn’t answer my question. Yes, you’re eighteen. But you live under my roof; I pay for your living expenses and expect at least a courtesy call or an answer when I call. I don’t know whether to fix dinner for one or two. So where have you been that gets you so distracted?” “I was with Janet, mom.” “So did you have sex? She still lives at home; I presume her mother approves of this? Did you stay at her house, a friend’s place, or get a motel room?” “Mom, come on please. It’s my life isn’t it?” “I just want to know what kind of girl she really is and if her mother is approving of you sleeping with her.” I figure she’s not going to let this go, so I tell her, well, an abbreviated version: “First of all we didn’t have sex, and yes we slept together. Her mom gave her approval because she knew it would be a losing battle with her daughter. She said we could spend weekends together but had to absolutely agree no sex.” “She really believes you’re going to sleep in the same bed and not have sex?” “Mom, we are adults and neither one of us is prepared to raise a child yet, so we agreed not to have sex. We did other things mind you, but not sex. “So I guess you are taking the Clinton defense and calling oral sex not sex? Well that would not have worked with your father; of course he would have never done that anyway. I don’t know how two young adults, just barely legal, with their hormones raging, will be able to keep from having sex while sleeping, probably naked together, for very long. At the least, keep condoms with you and in her nightstand drawer, just in case. You do know pulling out at the last second doesn’t work either, right?” “Yes mom, you told me that before. We are not going to have sex.” “Alright, nothing I can do about it anyway. So tell me about your weekend and more about this girl of yours.” I tell her about going to the fairgrounds and swimming in the pool, leaving out the no-clothes bit. She did ask about my swimming trunks; I told her I borrowed a pair that belonged to Janet’s father. “So are you going to be here or there in the evenings this next week?” “I’m probably going to be home but will go see her for a couple of hours after dinner.” “Ok, just keep me posted so I know how to plan my evenings. Sounds like I’m going to have a lot of time by myself. Dinner will be ready in 30 minutes.” “Ok mom, I’m going up to my room to do some thinking ok.” “Thinking huh? Now that is probably a good idea; use the brain on top of your neck. “Yeeesss mom.” Gee mothers. I go up and try to work this out. Let’s see: I’m in a cage, can’t masturbate, which is starting to really get to me. I don’t know how I’m going to handle 2 weeks of this. This is for 4 years; damn that now seems like a long time. What happens when I get tired of just giving her all the orgasm while being held captive and getting no relief of my own? I guess the tables are turned. I’m used to getting it all, leaving them wanting—no wonder they dumped me. Shit, I guess I’m not a
At least I’m being a good lover despite having my cock tied up. I’ve picked up how to use my hands and mouth well, so now it’s just about learning to better utilize the cock itself while locked away. It’s a win-win situation for everyone, yet here I am stuck with no relief. Damn it—either I’m thoroughly screwed or simply unable to get any at all.
I head downstairs for dinner, followed by cleaning duty afterward. Mom figures since she cooks, I should handle the cleanup. We hang out watching TV for a bit before I announce around 9:30 that I need some sleep.
“I bet you didn’t catch much rest last night,” she says. “Goodnight, Mom.” “Goodnight, Glen.”
My backside still hurts but is improving. The urge to jerk off is intense. How am I supposed to survive two weeks? And what happens when that time’s up? According to the contract, once it comes off, right away it goes back on. I need a few hours alone just to come at least twice more. I should discuss this with them—perhaps if I beg enough, they’ll let me out for another couple of days.
Later, I head to the bathroom, brush my teeth, and climb into bed still wearing the speedos. Exhausted as I was, it took about an hour to drift off; my mind kept replaying everything over and over. The desire to jerk off persisted, but touching myself wasn’t possible due to the lock. Eventually, waking up brought pain again.
Damn—I need to get to the bathroom now, hoping Mom doesn’t stir. I make it down the hallway and sit comfortably this time; the discomfort fades much quicker than before. After drying off, I replace the paper insert and return to bed. The clock reads 4:15, and sleep comes quickly.
