M.I.L.F. vs Stud Ch. 01

This is a continuation of "M.I.L.F. Takes Charge", available in my profile.

*

Much has transpired since I wrote about my encounter with the young buck who would make me his conquest, while I wished to make him my obedient submissive. Most of what happened, and certainly the most exciting, has transpired over this past summer.

I will write a short prologue to this story to bridge the gap between the first encounter and the events of the past summer.

I left you, as you will recall, with Derrick suggesting that I become his body building bitch and suck his balls dry every night. I admit, that was a tempting offer. If you saw what it was he had to offer from between his strong thighs, you would not blame me for kneeling before him, wearing his collar.

I fell asleep to that thought. I awoke when Derrick was walking back to bed, presumably from just having gone to the bathroom. His long cock bounced from thigh to thigh as he walked through the early morning light that filtered through the curtains. I dozed off for probably an hour, then woke to find Derrick asleep beside me, barely covered with the bedsheet. I saw the bulge of his morning erection resting on his lower stomach. I carefully peeled the bedsheet back to reveal his impressive manhood.

I thought seriously about taking it into my mouth and having my way with it until his fresh seed filled my mouth. But then I heard my daughter walking down the hallway to the bathroom. That's when I realized that the consequences of my actions would affect more than myself. By allowing myself to be collared, I am affecting Katye's future as well. Most assuredly, Derrick would have Katye collared and serving his sexual desires as well.

I did not raise my children to submit so willingly to a male. I raised both my son and daughter to understand that women were every bit as strong, if not stronger, than males and should stand their ground against them. For Katye's sake, as well as Kyle's, it was important that I not succumb to Derrick's lust; rather I needed to dominate him and collar him to illustrate to my family exactly where a male's place is.

As quietly as I could, I rummaged through my closet to locate some necessary accessories. Fortunately, Derrick was a deep sleeper, or perhaps just exhausted from the events of the previous day. Either way, I attached ankle and wrist cuffs to the bedposts, while also attaching a leather collar to the headboard by a one foot long chain. I quickly moved to secure his left, then right ankles to the cuffs. By this time Derrick awoke, but he was too bewildered to resist. By the time he was able to properly assess the situation, I had the leather collar locked tightly around his neck.

The boy was far too strong for me to wrestle his arms into place, so it would come down to a test of wills. Unable to sit up to uncuff his ankles, he began work on the collar, while protesting verbally. He didn't quite know if he should be scared, angry, or excited. I think he was all of the above.

I nonchalantly sat on the edge of the bed and reached between his spread legs and cupped his ball sac.

"You know, a woman can know everything a male is thinking just by observing what is going on down here between his legs. Your cock has begun to shrink a bit and your balls are tight to your body," I noted as I encircled his balls with my thumb and forefinger, pulling them down from his body. "A tight set of balls means that you are either about to cum, you're cold, or you're very scared. I think you are very scared about right now.

"Oh Derrick, I'm just having some fun with you. Relax! Listen, I want to lock you up and let you think about how much you could learn if you are willing to submit to me. I can't force you. I can't keep you tied up forever. But I would like to keep you locked to the bed for a few hours, just to give you a taste of what life might be like if you take me up on my offer to be my boy bitch. Why don't you just go ahead and lock the cuff around your right wrist. I'll take care of the left. We'll have a little fun, think about things, and I'll let you go in time for lunch."

He looked me in the eye, his cock twitched, and he reached over and locked the cuff around his wrist. By the time I cuffed his left wrist, his cock was as hard as I had seen it.

While I was in the shower, Katye knocked on my bedroom door, which was slightly ajar. Hearing no reply, she pushed the door open and peered around the side. "Oh my gawd!" She wasn't expecting to see her friend tied spread eagle to my bed. "Oh Derrick...all right, wow. Sorry, I didn't mean to intrude. Ummm, I'll just wait for my mom to come out. No rush."

Evidently, she couldn't resist the temptation. Before I was out of the shower, she let herself back in the room and sat down on the bed next to my prisoner. Without embarrassment, she lightly tickled his ball sac, giggling at him. Then she took hold of his shaft, pulling it straight up. "Damn, that's one hard rod. Oh, look at your balls; they're getting all tight! Don't be scared." She patted him on his inner thigh and left the room. I think that probably cemented his decision.

I walked back into the bedroom, still drying my hair with my towel. He didn't need to see my naked body, dripping wet, in order to be excited. He was as hard as I had left him. Dripping hard by now.

Over the next four hours, I made my way back in to check on my new toy. Only once was his cock not as hard as I would have liked. Each visit, I took about 10 minutes to stroke his cock, massage his balls, and lightly run my fingernails over his smooth chest. And each time, his ample precum dripped down his long thick cock and beads of perspiration dotted his body. I tormented him to the point that he fought against his bonds and begged for relief, which of course, never came.

Then, I allowed him to put that pent up frustration to good use. I straddled his head and slowly lowered my wet pussy lips to within an inch of his mouth. I let his instincts take over. He strained against his collar to lick. I teased of course, but relented eventually. I let him suckle my clit. His eager tongue first licked, then sucked, then upon my orders, dove deep inside my pussy as I sat hard against his face. I smothered him with my sex, and nearly drowned him with my orgasm. Once I regained my composure, I sat up, leaving his face covered with my offering, and him gasping for air.

Finally, in the early afternoon, I decided he had had enough. "Derrick, I'm going to release you. You can either let me attach this ball stretcher around balls, then put this on," I said, holding up his skimpy white Speedo, "and have lunch with Katye and myself out by the pool, or you can masturbate in front of me to relieve your pent up frustration and never see me again. I'll leave that up to you."

I thought I knew what he would do, but I wasn't sure. He stood, his cock throbbed hard against his belly, but he took the Speedo from me. He looked down at his member which looked back up at him, drooling. He took a deep breath, and with an ever-so-slight look of humiliation, nodded. It took me only a minute to lock the ball stretcher in place before he slipped his Speedo on, and tucked his rigid tool over to the side, barely covering it behind the Speedo. I surveyed his massive display of manhood, and walked with him down to the kitchen.

Katye couldn't contain her pleasure at what she saw approaching. She ran her hands over his chest, his perfectly round ass, then of course, over his bulge, barely contained in the stretched fabric.

After an afternoon of tanning, it was time for Derrick to leave.

"Derrick, I have but one more test. I'm going to remove the ball stretcher, and replace it with a chastity device. If you want to see me again next weekend, you will wear this. It is possible to take it off if you really try, but it will be impossible to put it back on without breaking the lock. I hope you will wear it, and learn from it. You will be surprised at what this will do to your state of mind, and any thoughts of dominance that might still be fluttering around in that pretty little head of yours."

"Each weekend that you spend with me, I'll remove it, but I demand that you replace it before you leave for the week. You'll wear it until you are either broken, or you decide that this just isn't for you. Okay?"

Again, he just nodded and stood stoically as I removed one piece of hardware to attach another. The problem was that he never lost his erection. And by the time I had the stretcher off, his cock was throbbing, begging for just a stroke.

"There's only one solution for this, Derrick. You'll have to believe me when I say this is the best thing for you."

I retrieved just the right paddle from my closet and told him to hold his cock straight out. Without hesitation, I administered two quick swats to his over sensitive cockhead. He let out a loud scream that only a male could make when his sexual organ is assaulted, but before the sting had left his cock, it was wilting into submission. I gave him one more good swat for good measure, and had the CB3000 on before he had a chance to recover his hardon.

It's amazing what happens to a male's brain when he is denied the ability to become erect or even feel his cock -- for five days.

Like an obedient pet, Derrick was on my doorstep at 6 PM on Friday. I fucked his ass several times; I teased him, and I used him. I had never felt such an eager tongue lapping at my pussy as his was. He plunged it deep inside me, nibbled at my clit, sucked me, then drank my juice as I came on his face, leaving him between my thighs to lick my pussy lips as I faded to sleep.

I did allow him an orgasm, but I can assure you, it was far from fulfilling. I took him just to the edge then stopped and watched as his cock churned out an impressive puddle of white cum.

Each week was much like that one. Some better than others. But with each week, Derrick fell further and further into submission.

Now, I will explain what has happened over this last summer, 2009. It has been very exciting, more than I ever thought possible. While I am quite capable of training a male, I received invaluable advice and support from a very dear friend. This friend recognized potential in me and knew that with a little guidance, I could be so much more. He mentored me and truly made me blossom into more than a mistress. With his loving mentoring, I have become a true Lady.

Our relationship started out friendly and polite enough, but has developed into something much greater. We have made a special connection that I wouldn't have thought possible thru email, yet we each feel strongly for one another.

Please read our correspondence, and enjoy. Truthfully, I have edited it to protect our privacy, but the message remains intact.

[Please let me know if you like the email format of this chapter. I have five or six more to post, so if many of you do not like the format or find much of our exchange to be irrelevant, then I will make changes for the proceeding chapters.]

July 3:

Well now, Mrs Millwood darling, what can I say?

Your story is fantastic and made me so horny. I am an author, and something of a master.

I shall think about your story and see where I can take it. I find the attraction you describe as incredibly erotic and it offers some interesting sequels.

I would love to hear from you, you sound like a very sexy woman.

Love

M

Hello M,

I am so glad you enjoyed my scenario. I have had several people compliment the story, but you are the first to promise to continue it. I am looking forward to seeing where you take it.

As for the names of my friends, I will give you a few. My dearest friend, well I suppose I have 2, but one is Heidi. She is going to be taking in my son, Kyle.

As a side note, Kyle was supposed to be away this summer visiting his father, and that's where he is now, but by August he will be back. I don't want him living here with me and Katye because Derrick has moved in with us, so I plan to have Kyle live with Heidi upon his return. She'll be great for Kyle. She's a very loving woman who will teach him well without being over bearing or stern.

My other dearest friend is Maize. She is as off the wall as they come. We tell her it's her Catholic school upbringing. She's the life of the party. She wanted Kyle to stay with her. Any if Kyle weren't my boy, I'd be all about it, but he is my boy, and as a mother, I can't mentally deal with the thought of Kyle being under her control. Oh lord, the things she would do!

I have 2 other girlfriends who comprise our group, but I'll leave their names/personalities to you, if you choose to write them in. One of them has a boy and girl, both good athletes in their teenage years.

I hope you will post your version of the story on Literotica. I posted a thread about this story with a link on the Story Ideas forum of the Bulletin Board, titled "MILF tries to turn tables on young stud." I hope you post your story on Literotica and add a thread to my original post on the forum, so others will know of it. I have received several emails expressing interest, but you are the only one who has promised to continue the story.

If you do not post it on Lit, please send it to me at this email address.

I will be posting my version in October, after this summer of adventure is over.

You are a Master? Do you have anyone collared right now? As a Dom, I have to ask, do you find it offensive that a dominant woman would take charge of a young male? I have always wanted to ask this question of a Dom, but haven't had the opportunity until now.

Thank you for your kind words. I look forward to hearing from you and where you take the story.

Mrs. Millwood

July 4:

Thanks Mrs Tina Millwood,

I have a plan in my head for you and I`ll get back to you very soon. I have a lot to say about you, a female Dom (Domna) controlling a male ---- You will like what I have to say but the critic who was very rude would hate me! I have a few suggestions for you also!!!

Warmest wishes and keep them all under your thumb!!

Lord M