Finding her love bud and sucking it in her hips raised as she let out a long soft moan coming from deep within. Her hips raised as her body undulated gently against my face, her fingers were in my hair both softly stroking as well as tugging me tighter to her pussy as she whispered.
"So good, so good. Oh my, oh yes, a little lower, just like that. What a tongue."
Before she even said she was getting close it was all too evident, her hips were rocking rapidly, her breathing was almost non-existent, her tummy beginning to tighten, she had let go of my head and was kneading both breasts, pulling on the nipples, smashing them to her body and moaning. With her hands clasped to the back of my head holding me tight to her body she let out a scream, her body was raised up off the mattress as she ground against my face, the room was filled with the sounds of, "Uh, Uh, Uh, as she left reality for a minute or two.
She lowered her body to the mattress as the climax subsided, in the process her thighs gripped my head, she didn't squeeze, they simply held my head in place. With her fingers still lingering and softly moving through my hair she raised slightly to look down, I peered over her hairy mons as she smiled.
"No man has ever eaten me to a climax like that, are you sure you're not a lesbian in a man's body, I hear they're mighty good at cunt munching. Then again, they don't possess a cock like that, nope, you're definitely a man."
I slowly crawled up her body resting alongside while I gently massaged her breasts, I hadn't taken much time with them earlier and wanted to make up for it. Pushing me onto my back she smiled devilishly.
"I've always wanted to do something I was never brave enough to do with Ted, he was sort of a prude in bed. I want to crawl over you and lower my tits into your mouth, I love having my nipples sucked almost as much as I love having my pussy licked. Would you mind if I did that?"
I smiled and opened my mouth like a little birdie as she crawled on hands and knees astride my torso, when her chest was aligned with my mouth she lowered enough to put a nipple into my greedy sucking lips. I played with and sucked them until her body shook, I'd never given a woman an orgasm just through tit action until now and I liked it, I was internally hoping this wouldn't be a one nighter. Her body was still shaking slightly as she scooted back, placing her hand between us she guided my cock to the opening of her vagina and pushed back.
She was wet as a waterfall, I'd been under the impression women her age didn't get that wet. I was pleasantly surprised, sure, I'd licked her, but this was not saliva wetness, this was pussy juice coating the head of my dick. As she lowered herself I could feel the labia being forced open by the head of my cock, she sucked in a breath, held it, and lowered herself onto my cock stopping with about three inches inside. As she exhaled she looked at me.
"Oh my God, I haven't had a cock in me for a long time, it feels so good and it feels uncomfortable at the same time, let me put it all the way in myself, then you can have me."
Her pussy was tight as a virgin, then again, considering her late husband hadn't been able to get it hard for over ten years and he'd been dead two, her vaginal muscles had retracted to the point of feeling virginal once again, and I was the lucky bastard that got to stretch them out. The walls were hugging my shaft tight as the head opened her, moving up and down slowly she continued working my cock deeper inside. When her ass hit my pelvis she let out a loud gasp, then exclaimed.
"It's in, I have all of your glorious cock inside me. Oh fuck, this is wonderful, my knees won't let me stay like this very long, roll me and make love to me."
I made love to her as she had asked, three times, the first was missionary where I dumped the biggest load, an hour later we fucked doggy where I dumped a second load and four hours later just before dawn with her on her side, left leg over my shoulder and me pounding her pussy like a jack hammer. I was exhausted, she was swollen and sore, we both needed a few more hours of sleep, waking just before ten in the morning. Following a shower she had breakfast delivered to the apartment, the lady who dropped it off looked surprised to see me at the table, Jenny explained after she'd left.
"I've never had a man here before you, we can be sure the kitchen is abuzz with juicy tidbits about you being here overnight. Knowing how gossip works they'll have me pregnant before tonight, doesn't matter that I'm beyond childbearing years and infertile, the rumors will fly unabated."
Following breakfast I was going to help clean things, when we had the dishes on the counter she told me that was enough, she paid the staff to take care of such things. I mentioned getting dressed and possibly checking in with work, she frowned.
"Will you be in trouble for not being at work?"
I shook my head, "No, I don't have set hours anymore, I'm what they call a floater, go in when I want to or if they call and need me ."
"Then stay a bit longer, I want to talk with you about something. First, how is it you can afford not to work? I mean not all the time."
I told her of my good fortune with the video games and that the amount of money people paid me to fix their screw ups of software and hardware programs I was pretty well set until I could make my dream a reality. When she asked what that might be I watched as her mouth initially fell open in disbelief and then became a smile.
"I want to turn your dads old five and dime back into a coffee shop that serves donuts, pastries and coffee at a reasonable price, none of this five bucks a cup bullshit. If I can provide a cup of coffee and a donut or pastry at a decent price it'll fly. People throughout the downtown area are sick of that over priced junk .... and don't even think about finding a donut or pastry, they're non-existent. If that flies there's enough space to open a bakery of breads and cookies only. I have my great-grandmas recipes from the old country, she never baked her bread in a pan, it was always round loaves like you see in Europe. That's my dream."
She was smiling as she took my hand, "Come sit with me, I have a proposition that may interest you. What daddy didn't tell you and would be upset if he knew I'm telling you now is that he has less than six months to live. He's dying of cancer, he refuses chemo or radiation, he just wants to go in his sleep, the doctors are managing his pain and that's all he wants. After watching my mother suffer through all of that when she died I can't blame him, at his age he'll just drift away one day and that'll be it."
I nodded, "So tell me about this proposition. Let me say up front I don't want to be a caretaker or anything like that."
"Oh good god no. This has nothing to do with daddy dying, this has to do with me entirely. I want you to be my lover. Last night was a trial run, I've met and considered a few others but I never felt at ease with them and therefore nothing ever happened, with you it was different, I felt like we clicked. I don't want a gigolo or a boy toy as my girlfriends call their young harems, I'm not looking for what is now called, and excuse my language, a fuck buddy, I want a lover."
My face must have said it all when I asked, "On first impression I don't think I'm interested, but tell me what my duties would be. Maybe I'll change my mind."
Taking my hand she continued, "That's just it, I don't want you to have duties or demands, I want you to be my lover, to kiss me and hold me, to take me out and let me be your arm candy. Yes, I know I'm propositioning you and I'll certainly take care of you, but none of them need to know that, all they need to know is that I have a lover. I want to be the woman you desire to take out and show off, not the young stud hired to screw and look boyish so the old hags can feel young again."
The more she talked the better I liked the idea, "Tell me more about this, you mentioned you'll take care of me. What does that mean?"
"Okay, I know you have money but I'll cover your rent if you want to live elsewhere, although I'd prefer you live here with me. I'll take care of food, nights on the town and the different charity events I attend, basically I'll cover your expenses within reason. I'll want you to upgrade your wardrobe for dressy events, other than that I want you in jeans and shirts just as you were at daddy's. I want a man, not a boy or servant, I don't mind paying for that luxury."
She adjusted sideways looking at me intently, "While daddy is alive I want you as my lover and escort about town which is usually three or four nights a week. You can work if you want, I'd prefer you don't, I want you to myself. When daddy dies I'm going to take a full year off and travel the world, Ted always promised he would take me but work was more important, heaven knows we had the money. I want you to go with me, I'll cover all expenses, by then we should be comfortable enough with each other that neither of us will feel like we're being used. Your thoughts?"
I wanted to be cautious before I gave her my answer, "I noticed you like being in control. How is that going to possibly work when I don't care to be told what to do? I'm going to want a certain level of autonomy. Would you have a problem if I took one of the bedrooms and turned it into an office where I can freelance, there are millions to be made in ones and zeros, some of it may as well come to me."
"See, that's the best part about this arrangement, I'm not hiring you as a boy toy, you'll still do your work, I'll continue to be involved with daddy's care and investments, but we'll be together. Take last night for instance, you didn't wait for me to tell you what to do, you took my body and did with it as you liked, which is what I want. As I said, I'm not looking for a boy toy, I want you to be my lover, my man if you will, and I emphasize the word MAN. I would expect you to treat me as *your* lover in every way."
She had my interest, "It sounds reasonable, you're attractive, fun in bed, kind, and though you tend to be bossy, I think it's because there's no one to say "wait a minute", who you're willing to listen to. When would I start and what are the rules, there are always rules."
She smiled, pulled me to her body and kissed me passionately before pushing me back.
"I love how you think, I know this will work. There are basically three rules, you treat me with respect and never purposely hurt me, number two is if you ever treat me like a slut or whore it's done and I will destroy you, number three is simple. I shave my pits and my legs, the rest stays as God designed it, you didn't seem to mind last night so that's probably a moot point."
I chuckled, "Those are pretty simple rules to follow, I don't mind mumbling in the moss, I prefer a full bush like yours, I want you to look like a mature woman and not an eight year old or a porn star. You didn't answer everything I asked though, actually I have two questions. When would I begin and what will you expect of me after the year abroad?"
"If you're serious the answer to question number one is you started last night. As for question two, I'm honestly not sure, I haven't thought that far ahead. Why don't we see where life takes us, we've plenty of time to contemplate what we'll do when the time comes."
Knowing we were naked beneath our robes I was pulling her to me when she put her hand on my chest, "I may be sore and swollen but if you open this robe you're going to have to take me again. Oh, rule number four, we may use words like pussy and cunt and cock and fuck in the bedroom, but they are never to be used for public consumption. If you make love to me now you are agreeing to my terms. The ball is in your court."
I opened her robe and softly took a nipple into my mouth. Two minutes later she had my robe open and my throbbing cock in hand as she lay back with legs spread. Thirty minutes later we were in the shower once more, it was there she informed me I was to go to a given men's store and tell them I needed a tuxedo for the night, she would call ahead and make sure they were prepared. I was to go get my overnight items and return to the apartment, she would give me keys and inform the doormen I would be staying in her apartment from here on.
As I was getting dressed and ready to leave she was on the phone, upon hanging up she sidled next to me in a sexy manner. With her arms around my neck and her body pressed to mine she talked softly.
"I want you to bring enough casual clothes and toiletries to last a week minimum, I'll take care of your formal wear, by the way, these are not rentals, they will be permanent so no adding fifteen or twenty pounds. I want you to think about how soon you can move in completely, as for tonight you're escorting me to a charity event I host every year at the children's hospital. Now scoot, your car will be waiting at the curb, I'm gonna check on daddy and I'll be back by five, be showered, shaved and ready to go when I get here. Bye lover."
My car was waiting for me to beat feet over to the men's store, I loved the name, it said simply *Haberdashery* in bold black letters against a white background. The place looked old from the outside, seasoned if you will, walking in confirmed that thought, it was up to date and modernized but still had many of the items found in stores circa the 30/40's era. Introducing myself they hustled me into a back room where two men and a woman basically undressed and redressed me in a tuxedo, a suit and a slacks/sport coat combination complete with new shirts and ties. I was to return by four to pick up the items needing alterations.
They directed me to a given shoe store where people would be waiting for me, having normal sized feet I was fitted with three new pair of loafers and a pair of black leather oxfords. I hadn't worn a pair of tied dress shoe since I couldn't remember when, I sure liked the soft leather and fit of all four pair. From there I want to my apartment to gather toiletries and clothes, by the time I was done with that it was time to pick up my clothes from the haberdashery. Pulling up to her apartment building I wasn't quite sure what to do, as I sat looking at the entry a young man came out and opened my door.
"Good afternoon Mr. Gentry, I'll take care of your car sir, the keys will be in the valet office, just call down when you need to leave, we'll have it out front and waiting."
I was looking for a valet cart of something of the sort to unload the packages and my bags, the young man told me to leave it, the items would be brought to the apartment within the next ten minutes.
I found myself daydreaming as the elevator ascended, this was an entirely new world to me, a farm kid who made a go of it in IT and yet here I was, I'd be living with a wealthy woman, as her lover. Never in my wildest dreams.
By the time Jenny arrived I had showered, shaved, thrown on some British Sterling cologne and was waiting on the couch in my tux, I had to admit when I looked at myself in the mirror I was one handsome SOB. I stood when I heard the door lock, Jenny walked in the door and into my arms, I plastered a kiss on her sweet loving lips and welcomed her home. Standing back she smiled,
"I'm not sure taking you with me is a good idea, the women will be hitting on you all night."
"Not to worry Jen, I'm with you and we're together, there won't be any fooling around. Right? I mean, I don't want you with other guys."
"See, there's that thinking again that I like so much. No, no other guys will win my affection, but I want you to be careful. There will be women at this function who would take you in the women's room and screw you, hell, I know of one or two who'd drop to their knees and blow you in the hallway. I'll need to schmooze and socialize so we won't be with one another entirely, but I'll need you to look out for me, some of these bottom feeders think that because I'm widowed I must be craving their cock. And while there is a cock I crave, it isn't theirs. I need about twenty minutes and we'll head out."
Being a boy at heart I needed to peek and see what she was wearing underneath, when I walked in the room she was in a soft yellow sheer bra with matching stretch lace panties and black diamond patterned thigh high stay ups. Seeing me she shook her finger at me as she spoke.
"You're a naughty boy, away with you, it'll all be here for you to undress when we get home."
Ellis was at the door waiting for us as we left the building, he escorted us to the Merc, opened the door for us and helped Jenny in, I walked around the car and got in the other side. Pulling away he asked if she wanted the privacy screen up or down, she told him up.
"Derek we need to be less formal tonight, as far as what we call each other, I've been thinking about it all afternoon. Do you mind if I call you dear instead of Derek? You can call me Jen or Jenny, whichever you'd like."
I smiled and took her hand, "Can I call you lover girl?"
"In bed but not at this event. Speaking of bed, baby I can't do every night what we did last night. Hopefully I didn't get your hopes up."
I laughed, "Thank you Jen, thank you. I wasn't sure how to tell you I haven't ever fucked four times in a twenty four hour period before, my dick felt like it was ready to fall off after our little romp on the couch. We'll do it when we feel like it, not when we think we have to. Okay?"
"You? I could barely touch between my legs when I showered, it was so swollen and touchy, you stretched me in ways I've never been stretched before, I'm not complaining because I sure want more of that monster, just not tonight honey. It hurts to pee I'm so puffy."
"Okay then Jen, no cock tonight. I'm not sure I could get it hard anyway."
She sat back staring slyly, "Is that a challenge? I think my oral skills can get that bad boy standing up in less than two minutes."
I pulled her close, "Okay, you win, I'm sure you're right. You are one talented cock sucker."
Touching my cheek with the back of her hand she mildly admonished, "That language stays in the bedroom, don't forget. I like it when you tell me what you're going do to my body, but that stays in the bedroom."
"Jen, I need to ask a favor. Would it be okay if I opened doors for you? I'd like to be the one helping you in and out of the car."
Leaning into me for a kiss, a long lingering soft kiss she backed away smiling, "I would love that, I'll let Ellis know, he's done it for so long it's become second nature to him. Thank you."
Pulling up to the gala event she told Ellis over the intercom that I would be opening her door from now on if we were together. As we stopped I went around to her side of the car and opened her door, I had to admit she looked dazzling as well as stately, she was in charge of the evening and she let people know it without saying a word. There was every size, shape and color in that ballroom, Sikhs in their turbans, Muslim women with the traditional head scarf, some kind of sheik looking guy with the rag around his head and long flowing clothes, white people, black people, there was even an American Indian in a suit with long braids and feathers on the ends, as I said, every size, shape and color.
Jenny introduced me to a few and then began to make her way through the crowd shaking hands, hugging women and generally making her presence known. When it was time for the meal she found and sat with me, we exchanged pleasantries and agreed we would find one another after the ceremony.
I noticed one guy in particular who was always next to or very near her, she didn't look frightened by him but she certainly looked uncomfortable. He looked to be late forties, early fifties, obviously a businessman of some sort and what appeared as pushy. The evening was winding down, and though I hadn't necessarily been at her side I was always within a few steps away, she would look for me and smile.