Chapter Four Caught Off Guard
I awake feeling great, I had lost a lot of sleep over the last few days, and I finally feel caught up. The fact that Diane had completely exhausted and drained me last night made it easy to sleep so deeply. As I lay in bed I replay the whole evening in my mind, it really was fantastic, better than I could have ever imagined, I can't wait to do it again. I can't stop thinking about Diane, I would have loved to have spent the night with her, I have this incredible urge to see her, to be with her. I'm surprised I have these feelings, this infatuation with a 44 year old woman. Not that she's some old hag, she's very attractive, she's in great shape, and looks fantastic for her age, but I've gone out with some hot 18 year old girls that I haven't felt much of anything for. I know Diane said not to call her, but I don't know if I can resist contacting her. Do I really have to wait for her to contact me? That seems so crazy. When will she contact me? Next week? Next month? This is the kind of lack of control I don't like. Maybe last night was the first and last time. No, I doubt it, I could feel that she enjoyed it as much as I did. Maybe she's lying in bed right now having these same feelings about me….or maybe not. I know she has a few partners, and I'm just a kid from next door. This didn't bother me before, but now the idea of her being with someone else, another guy, is not sitting well with me. It's uncomfortable to think about, so I don't. I roll out of bed, I need to be at the bike shop for noon. As I walk out of my house I look over at Diane's, it seems to be dark, her car is gone, she's most likely at work. Luckily the shop was busy which made the time fly, but more importantly it kept my mind off Diane. As I'm leaving work I check my messages and notice a voice mail from Diane, my heart races with excitement. Her voice was very calm and emotionless.
"Hi Jack, it's Diane. Listen, I want you to be over at my place at 9:00 tonight. Be sure to use the back door, see you then."
Her tone is odd… cold….. I don't hear any excitement in her voice, maybe she wants to pull the plug on this thing that we just started. She'll probably tell me that it was a mistake to get involved with me, I'm too young, I'm a neighbor, and this all just wrong. OK, no problem, I can handle it, there's plenty of other woman, no big deal.
It's almost 9:00, I tell my mother I'm going out for a bit, I drive around to Densmore St and park before walking over to Diane's. I knock on the back door and this time she almost immediately opens the door. She invites me in, she appears to have just gotten home from the salon.
"Come in Jack….. how was your day? How was work?" She asks.
"It was OK" I reply, hoping she doesn't start off with small talk before she gets to her ''Dear John'' speech.
"That's good, because your night is going to be a whole lot better, now strip." she demands.
"What?" I reply. I'm completely taken off guard, I didn't see this coming at all.
"You heard me, Strip, I want you naked." she barks.
I quickly start to disrobe, and within a minute I'm standing naked in front of her, my hands behind my head and legs apart. She looks me up and down, her eyes seem to come to rest on my dangling cock and balls.
"Good boy, you even remembered the correct stance, now follow me." she says.
I follow her into the bedroom we were in last night, the room with the big, wrought iron, four poster bed.
"On the bed, lie face down." she orders. Her voice is less playful than last night, more curt and to the point, slightly angry, is she going to punish me? What for? I haven't done anything to deserve it.
I lay on the bed and she attaches the leather cuffs to my wrists and ankles. The cuffs are then attached to the bed posts, and she manages to pull the ropes even tighter than last night rendering me completely motionless. I don't believe my legs can be spread any further than they are now, I feel very exposed and vulnerable.
"I almost forgot what a great body my slave has, not an once of fat, so toned, and this position really shows off your tight ass." she says.
"Thank you Mistress." I reply.
"Don't thank me quite yet." she says.
"Why Mistress? What are you going to do to me?" I ask.
"Don't you worry my little slave, I have some delicious plans for you." she replies as she lightly caresses my back with her fingertips. She finishes by running her finger down my spine and through my separated ass cheeks and over my anus. It feels very erotic, as it reminds me how exposed I am, I feel my cock surge. I can now feel her hands on my balls, I quickly realize that she is binding them with rope, they're quickly secured using what feels like a slip knot. Moving to the front she begins to fit me with a ball gag, but this one fits over my whole head like a harness. To my horror, she then takes the long rope that is tied around my ball sack and attaches it to the back of the ball gag harness.
"Now lift your head up off the bed as far as you can, while I tie this little rope to your harness. Good…very nice…..well, it looks like you've gotten yourself into quite a predicament. Just keep you head up." she laughs.
Oh God, my head is tied to my balls! If I relax my neck at all, the weight of my head will stretch my balls, I'm not sure how long I can hold my head up, or when my neck muscles will give out. How long is she going to keep me like this????
"I'm going to get out of my work clothes and get into my 'work you over' clothes, I should be back in 10 or 15 minutes. Now you just keep your head up." She teases.
15 minutes? Oh God I hope I can last. I think back over the last half hour and the turn of events that have taken place. I came over expecting Diane to tell me she wanted to end this relationship, and 20 minutes later I'm naked, gagged, tied spread eagled to her bed, and my balls are on the verge of being stretched by my own doing. I'm starting to feel the fatigue in my neck, even if I relax my neck a little I can feel discomfort in my balls, luckily within a few minutes Diane returns.
"It looks like my slave boy has done well, your head is still up and you haven't tortured your pretty little balls to much." she says.
I can hear her taking pictures behind me, my eyes are closed as I try to deal with the fatigue in my neck. She begins to lightly stroke my tortured sack.
"Very nice….there's nothing I like better than seeing your sweet plums bound up like this….nice…and….tight…. You know, for the last year or two I've fantasized about you… having complete control of you….but imagining gets old…you've been tantalizing and teasing me without knowing it….. it's been frustrating having you so close, yet so out of reach….so I seem to get some sort of revenge by torturing the essence of your sex." she states.
"I think you've earned a little freedom." she says as she unties my balls.
She reties the rope to the footboard, keeping my head elevated from the bed, but at least my balls aren't taking the pressure.
"You know I keep coming up with good ideas, and last night I came up with one, do you remember?" she asks.
Hmmm, I think back, trying to remember what she may have mentioned.
"Do you remember I mentioned this?"
Oh God, it's an enema bag, that's right, now I remember. She threatened to tie me face down on the bed and give me an enema……and she already has me bound face down. Oh God No….I try to protest through the gag, I try to struggle to free myself, but she has me well secured, and I know this only excites her anyway.
"Don't be a bad boy, I know you want to be all clean for your Mistress, inside and out."
This is going to be so humiliating. I can't believe it. Diane is going to fill my ass, and I can't do anything about it!?! What makes it worse is the more humiliated I become the more excited she becomes.
"Let's see, I have a few different nozzles that will fit nicely into your bum bum, which one do you think I should use?" she asks.
She shows me an assortment of nozzles, some are pear shaped like small butt plugs.
"This one? This one? This little one?" she asks, knowing I can't answer.
Thankfully she chooses a thin, straight one and begins to lube the nozzle as I watch, contemplating where she'll soon be putting it. I try to beg for her to reconsider, but the gag prevents my words from reaching her.
"You really have the sexiest little ass, so hard and lean. And look at this little asshole, still so tight." She says as she gently runs her finger up and down the crack of my well spread ass cheeks, before she lightly probes my anus.
"I think it's time we get you cleaned out, don't you Sweetie?" she laughs.
I attempt to plead as I feel her slowly start to push the nozzle in until it fully enters me. I can then feel her attach the hose to the nozzle and the bag. Then again, more pictures, I'm really starting to wonder why so many.
"Now aren't you just a sight, all bound up for punishment. That hose running into your ass looks absolutely delicious." she purrs.
"There's a little valve on the hose that will allow me to fill you up, but before I do I'll give you a chance to get out of this predicament. Lying face down I can't see your cock, so the deal is this: if you've been able to control yourself and do not have an erection I'll remove the enema, but if you haven't been able to control yourself and your cock is hard I'll fill you up." she says.
Oh no, I've already lost this deal, I can feel my hard cock squeezed between my stomach and the mattress.
"Now I just need to check your penis." she teases as she slides her hand up from below my testicles and grabs onto my cock.
"Uh Oh, I have a bad slave boy with a very hard penis, that means he wants his punishment." she laughs.
''A deal's a deal, so sorry sweetie." she laughs as she opens the valve and I feel water flow into my ass for the first time. Initially it doesn't feel too bad, and I can tell Mistress is thoroughly enjoying my humiliation, which in turn gets me excited. She begins to untie the rope that's holding my head up, and then removes the harness gag which is a relief. It's short lived because now my bowels are starting to cramp.
"Almost done Sweetie…..there, that's it….do you feel full?"
"Yes Mistress, I'm full. It hurts." I say
''I'm going to untie you then you can use the bathroom. After you empty yourself I want you to quickly shower off, I want you clean inside and out." she instructs.
It seems like it takes forever before she releases the cuffs and pulls the tube out of my ass. Trying to keep some dignity I calmly walk to the bathroom, even though I want to run. It's a huge relief emptying my bowels, the best part of the enema, for me anyhow. I quickly shower before returning to the room, wondering what Mistress has in store.
"Good boy, nice and clean. I'm not done with you yet, not going to let your hard-on go to waste, now get back on the bed." she orders.
She has me kneel at the bottom of the bed with my ass against the rails that make up the footboard. She cuffs my wrists and ties each one to the top of the posts over my head. She then runs rope around my knees and ties them to the posts spreading my thighs apart. Not stopping here she ties my thighs and waist to the rails in the footboard, rendering me immobile from my waist to my knees. She then attaches a set of nipple clamps, which to my surprise are fitted with bells.
"Now don't you just look precious." she laughs
I certainly feel embarrassed in this position. I look down at the clamps and bells, which jingle at the smallest movement, and my fully erect cock sticking straight out, which gives away my excitement.
''Since your ass is nice and clean I might as well take advantage of it. I have a fun toy that I think you'll like, do you know what these are?" she asks.
"No Mistress." I answer as she holds the toy up.
"They're anal beads. I'm going to slip them in your bum bum, they feel good going in, and even better coming out, especially if I pull them out while your cumming." she says.
I moan in pleasure as she tells me this. The toy consists of five balls connected with a string which runs through the center of each ball. The balls are spaced about three inches apart with a ring at the end which Mistress is holding the toy by as she is lubes each individual ball. She then walks behind me.
"I think you're going to like this, here comes the first one….oh it slipped right in, nice….here's the second." she says.
Thankfully the balls aren't too big, they go in easily and they do feel good, my cock is throbbing at this point, the tip wet with precum. She finishes inserting all the balls and then ties a long, thin rope to the ring at the end. This rope is run under the cross rail just above the mattress, Mistress leaves the rope on the mattress in front of me.
"Very nice, you're naked, bound, and ready to fuck. You look so natural like this, I wish I could just keep you here as my sex toy, you wouldn't mind that…would you?" she asks as she slowly starts to undress, teasing and taunting me as she goes.
"You wouldn't mind sucking these tits…licking them….fucking them…hmmm? And what about what's in here…..you wouldn't mind keeping my pussy clean….you've got a talented tongue…good for licking…making me cum…you wouldn't mind that….cumming inside me….I can train you to cum on my command….hmmm." she slowly taunts.
She now stands naked before me, her body perfectly proportioned, medium sized breasts with only a hint of sag, thin waist and nicely toned legs. Her blonde hair framing her beautiful face. She slowly makes her way onto the bed, and onto her hands and knees. She positions her ass right in front of me, reaches under and grabs my cock and begins to slide the head along her wet slit. I immediately start moaning and she slides me completely inside her. The feeling of finally being inside her is tremendous, I hear myself quietly moaning in pleasure as she slowly begins to slide herself on my rigid cock. I can see that she has the rope that's connected to the anal beads laced through her fingers. Soon she also begins to moan softly, but manages to converse with me.
"Slave, you feel so good!….. and remember, you have to ask permission to cum, I want you to try to last as long as you can." she says
"Yes, Mistress." I answer, but I don't think I can last too long, especially if she starts talking erotically.
"I'm going to pull out the beads at the same time, you're going to cum so hard, it'll be very intense…..mmmm….I know how sensitive the head of your cock gets…mmmm…when you cum, but I have you bound up so well….mmm….you won't be able to stop me from fucking your overly sensitive cock…mmmmm….it'll be torture for you." she says.
True, I won't be able to stop her, I can't move my lower body at all. I can hear Mistress moaning, along with bells that are biting into my nipples, but I don't think she's close, even though I am.
"Mistress, I'm getting close, I don't think I can last much longer." I tell her.
"Then you have to ask your Mistress if you can squirt your boy cream out of your cock" she instructs me.
"PLEASE MISTRESS, CAN I SQUIRT MY BOY CREAM OUT OF MY COCK?!?!!" I scream!!!
"Yes, slave boy squirt for me, squirt!" she says as she pulls the beads out of my ass and my cock explodes into the most intense orgasm I've ever experienced. The beads and the orgasm blending into one huge wave of pleasure. I can hear myself grunt and scream wildly as the bells ring uncontrollably with my upper body contortions. Mistress continues to fuck me as I try to escape her pussy, the head of my cock so sensitive it's turning pleasure into pain. Oh God, I can't take it.
"Stop, Mistress, please stop, please, please, oh God, please" I beg as she just laughs.
"Haha, no baby, I love to see you tortured, it's so hot! ...Mmmm."
Finally the sensitivity passes, but Mistress continues to slowly fuck me, and to my surprise I still seem to be hard. Mistress begins to taunt me to ensure I don't get soft.
"You may cum quickly, but you're still hard….which is good, because if you go limp I'll definitely have to punish you for cumming so quickly."
She now begins to rub her clit as she pumps her pussy on my cock.
"Mmmm I love your hard, young cock inside of me…mmm…soon I'll be able to slide my strap on inside off you…. once I loosen up your sweet ass a little more….mmmm…..I love hearing you scream when you cum….mmmm….sweet screams….yeah…mmmm….don't you dare cum slave…..or I'll put your little plums in my ball crusher….mmmm….then you'll scream….oh it feels so good when you fuck me….ohhh..mmmm….I think…I think I need…to cum…mmmmmm….MMMM….OHHHHH GODDD….OHHH…GOOOOOODDDD…I'M CUMMING…. FUUUCK…AHHH….AAHHHH…..AAAHHHH…AHHH…MMMMM…..MMMMM….mmmm……mmmm…..ahhhh….."
Mistress has an intense orgasm, my balls are dripping with her juice. To my surprise, almost as soon as the orgasm has passed she's on her way to another one. I've heard woman can do this, but don't know much about it. After her second orgasm she rests her head on the bed, quietly moaning, her ass in the air with my cock still inside her. After a few minutes she rises to her feet and begins to untie me.
"What a great little fuck you are, I wonder why I'm untying you, I should just leave you here for later, your cock still looks like it's ready to go." she whispers in my ear.
"Thank you Mistress, I'm glad I've pleased you." I reply back.
"I'll admit, I was a little concerned when you came so quickly, but luckily you maintained your erection.'' she replies.
"Yes Mistress, I was too." I said.
"Lie down with me on the bed." she instructs.
"Did you like the beads? Did thy intensify your orgasm?" she asks.
"Yes Mistress, very much." I answer.
"I like ass play and CBT, but you've probably figured that out by now. What are you into? Is this what you imagined? Are there other things you want to do?" she asks.
''Yes, so far I've loved everything. I love the way you speak to me, the way you threaten to punish and humiliate me, it makes my heart race. I like being tied and unable to move, to give up all control to you. When you tied up my cock and balls last night, that was very erotic. I sense you get off on it too, and the more it excites you the more it excites me." I respond.
"OK… good…. I want to push you a little further, a little more pain, a little more torture. Some people really get off on pain, are you like this?" she asks.
"I don't think I get off on pain really. I can take some, especially if it excites you, then it will excite me, as I just said." I reply.
"So your not a pain slut, which is fine, we'll go slow. Last night I mentioned when I was a little girl and the first thoughts of this stuff, how I fantasized about the boys in school, and Batman and Robin. I haven't thought about those things in decades, but it got me thinking, Jack, I'd love to do something like that to you, to slowly torture you. I don't have any solid ideas, but I think it would be so hot to hear you whimper as you try to escape your impending fate." she tells me.
"I'm willing to do anything, it sounds exciting. Let me ask you something, and you don't have to answer it. When did you get into this, and who else do you do this with, I know I'm not the only one." I ask
"Ahh, I figured this would come up. Well I haven't been doing it very long, just a few years. My husband wasn't into it, so I guess I repressed it for about twenty years. The internet ignited these feelings since so much information became available. I got divorced for many reasons, sexual satisfaction may have been one. Once divorced I was free to embark into this lifestyle. I do meet with a few men on a semi regular basis, they're all married, their wives let them do this with me, or so they say. I'm very selective, I don't charge money, I'm not a pro, it's mutual satisfaction. I'd really just like to have one partner though." she says.
"Interesting, you've certainly learned a lot in a short time." I say.
"Maybe, natural desire goes a long way. So you mentioned you wanted to tie me up, are these thoughts you've had for a while, being dominant I mean?" she asks.
"I few years I guess, I never thought of being dominated, didn't even know female domination even existed until not long ago. I first thought it was strange, but the more I thought about it the more exciting it seemed. Have you ever been with a woman?" I ask.
"Ha, I bet you just love the idea of two women together don' t you, you boys are all the same. To answer your question, yes I have. Only super hot women though….I tie them up tight with their legs spread, suspend them from the rafters, put clothes pins on their nipples and pussy lips, fuck their tight asses, and eat them until they cum all over my face! Is hat what you wanted to hear??!" she laughs.
"Mmmm, Wow!! Sounds great to me! Really?" I say.
"No,I was kidding, well some of it anyhow, but I have been with women." she replies.
"It's getting late, tomorrow is Mother's Day, you should get going, maybe I'll call you during the week."
"Fair enough, yes call me."
I get dressed, she gives me a deep kiss before I head out the door.