Extending the MILF List Ch. 02

The next morning was a whole new version of weird. My sisters were nice to me! They fixed me breakfast, the first real meal I had had since just after Thanksgiving. They tittered and hovered and cooed about me like I was suddenly transformed into some teenage idol they had fawned over as girls but only now had the chance to share his presence. If I had not been so distracted by my own situation, it would have been incredible, after all this time of being punished by my house full of females, to experience their subservient attentiveness. My every wish was their command and they contended to see who would hand me the butter for the pancakes or heat the syrup or pour more coffee or orange juice. I felt like I was suffocating in the cloying closeness of too many orchids. Their smell interlaced with breakfast sausage and the pancakes was not orchids but a flower of an entirely different variety or should I say "flowers?"

Since I had slept till noon, my study time was truncated. D. Debra called about four and asked if we were going to go out. Instead of giving me any indication of what she wanted, she asked and fell silent. When I did not speak for a minute, she finally sighed into her phone. "Sonny, be the man now. I, I want your lips on me tonight so, so do something to take my breath away."

Images of her bare breasts, topped by the tangled bra and the rolled ridge of her sweater threatened to swamp my brain but then I rallied. My mind cleared and I had the perfect plan. "Wear something elegant, the best you have that is easy to remove." I almost chuckled when I heard her suck air between her teeth, a lurid little hiss on her end of the line. "I'll pick you up at seven."

I hung up on her. First time. I felt like the last day of school, a curious freedom. I rubbed my eyes though, trying to dispel the image of her naked breasts, right there in front of me, unkissed but so very desirous of my attention. I called the Bedford and found I could get a reservation for eight thirty, curiously only after they asked my name did they have an available table. I picked Ms. Hamilton up at seven-thirty. I went to the door of her house and she opened it. When she made to push past me, I asked, "Aren't you going to introduce me to your mother?"

She froze for a moment, then shook her head. "Not home." She said shortly. Her eyes focused on the suit Mr. Cheng had given me and she whistled. "Sonny, I did not know you had any sense of style at all." She fairly whispered. "Oh my, but you look handsome, dashing, debonair. I do believe I am light headed and slightly underdressed. You may actually make me look shabby in comparison." She actually sounded pleased by the statement.

"I resemble that remark." I said, lifting my chin in a haughty impression of the man I was never meant to be. "I am glad you can appreciate the finer things in life." She, however, was anything but shabby though I confess visions of her voluminous bare breasts danced in my head instead of sugar plums.

She smiled that spotlight smile and we left. She squealed when we stopped in front of the Bedford. We emerged from the car leaving it to be parked, and went into the Gainsford and were immediately seated, though we were early. The waitstaff did not blink when I ordered wine or ask to see ID. I had gotten a paid-in-advance credit card with Mr. Cheng's cash and used that to pay for the meal of lobster et al. It was wonderful. We left the car with the hotel and sauntered though the Christmas glitter of downtown. She did not talk at all, but held herself close to my arm. Deedee wore a white faux fur coat that barely covered her arms and almost touched her waist and still managed to accent her incredible, edible breasts! The dress sparkled with little bits of crystal. It was almost turquoise but not as intense. The crystal was strung on little silver lines that ran vertically over the entire dress. The front of it parted at the waist, forming a very revealing V on her torso. It left the half bra clearly visible, barely covering her breasts. The fabric ran just over the point of each shoulder. With a gentle shove, it would slip off her shoulders, leaving her breasts cupped by the matching bra. I know this because that is what I did once we arrived back at her house.

We'd walked an hour and the meal was perfectly settled before driving to her house. I turned off the car and she immediately shrugged the snow-white fur coat off of her shoulders. She twisted in the seat in Georgia's coup and waited, her hands folded in the valley of her thighs. I did not hesitate. My hands shook as I pushed the fabric over the notch of each shoulder and watched as it shriveled down her upper arms. One side caught on the bra but the other side slid free, uncovering the top of her crinkled aureole. Dee Dee sucked air between her teeth. With my trembling help, she withdrew her arms from the glittering dress.

"It fastens in front." Dee Dee said, her voice tight. "Kiss them. I cannot wait." She swallowed hard and that put a waver into her breasts that made me feel faint.

I found the clever hook worked into the crystal between the cups of the bra—obviously designed to be seen, to be exposed to public view—it had the virtue of supporting and enhancing her fine breasts while keeping them sufficiently covered to entice without getting arrested. Any man looking at her would have become a criminal and should have been arrested...and she was sitting there waiting for me to touch her, waiting for me to kiss her breasts to see if she would come.

Suddenly I was nervous. My cock shrank from fear and performance anxiety. In a moment, I became a quivering bucket of cowardly goo.

But then the MILF list came to my rescue. The horrible fear of failing to measure up to this woman's erotic demands lessened when I considered that I had been ignoring Mrs. Honeywell and that, so far as I knew, I could call her up and have her at nearly any moment my whim demanded. Just the thought of the dark and beautiful Mrs. Honeywell bent to my will snapped my cock back into shape. I took a deep breath. That awful moment of doubt had happened in the time it takes a gnat to sneeze and then I was past it. I released the crystal catch between the woman's breasts and the bra slipped down and out of my focus.

Dee Dee immediately put both of her hands on mine and in imitation of similar moments, she positioned my hands to cup and massage her breasts. My palms quit itching. The plush feel of her breasts in my hands consumed all my attention and awareness, even to the point that I quit breathing. I did not notice I had stopped till Dee Dee spoke.

"Oh please, kiss them!" She sighed.

I did, hesitating only long enough to take a slow, quavering breath.

D. Debra sighed more profoundly in anticipation, a fact that inflated my ego et al, and left me eager to be of service. Her hands rested on my shoulders as I bent over the car's console between us and touched my lips to the side of one breast for the first time. She groaned, "Oh god!" and her head snapped back as though struck with a right hook, appearing out of nowhere. My lips sucked at her skin and she hissed, "Yes, please, oh please."

I could feel her trembling. Her whole body shivered. I intentionally kissed around the aureole, but then licked over it when I could no longer resist. The rough feel of the crinkled flesh on my tongue exceeded even my well-tuned imagination. Her reaction was far more gratifying than I had any right to expect. Her hands grasped my shoulders and both held me in place and sought to pull me closer, all at once. When I sucked at her skin, she hissed and then arched her back, pressing her breast firmly against my mouth. When I sucked at the rumpled inverted nipple, she groaned, her hands claws on my shoulders. I sucked and kissed and then licked around the breast till she squeaked.

"God, Sonny, yes Sonny. The other, please, the other."

I compiled, since it was such a good suggestion. A woman needs to know you will or at least can respond to her wishes. I did. Unlike the gentle treatment on the left breast, I sucked her right breast very, very hard. When my teeth nipped at her, she shrieked and her whole body bucked, first crashing against me, mashing her breasts into my face then she fell away from me, slumping into the corner of the car door and her seat, out of my reach. She twitched for a minute or two before her eyes opened. The eyes opened heavily, regarding me like a drug addled princess looks at a talented eunuch. She smiled lazily. Without a word, she pulled the fur about her shoulders, and virtually naked from the waist up, she tottered to the front door, fumbled for a key and disappeared into her house.

Sunday, for the first time in more than two weeks, we did not talk or see each other. Finals were upon us and I was smothered with work. When I lifted up my eyes from the books, visions of her breasts tantalized me, lingering right there, before me like a phantasm of my own making, but she was real. In fact, we did not speak till the next afternoon. I called her.

"I wondered if you were going to call. You did not call yesterday." She said without any greeting when I did finally call her.

"Neither did you." I responded. I was beginning to regain my balance with this woman, recovering my MILF-confidence. I was still sex addled around her but I was regaining some of my sputtering elan, evening things out a bit and she seemed to respond to the assertive behavior that had opened the thighs of the MILF List. "Feel like a pizza?"

"I hope not or all the skin cream I use is just a waste of money."

I chuckled. "I have three more finals. Then it is time, uh, school will be over. I have got to study till then. Scholarships and poverty."

"Pizza then study."

We seemed to be perfectly in step. It was indeed pizza then studying at the library. When we broke at midnight to go home, we kissed at the car and I took her home. Parked before her front door, she opened her coat and casually unbuttoned her blouse. She unhooked the front of the bra and waited.

I leaned over the console and sucked at the breast closest to me. She hissed and cooed, "Yes, yessss."

Back and forth between each breast, I kissed her gently for a while before sucking each breast hard. I had the urge to mark her but thought that would be gauche. I found the nipple, fit my mouth fully over it and sucked till she grunted with satisfaction. Her hands locked on my shoulders till I moved to the other breast. She hissed and after a minute of my attention, she came again, quivering and jerking as the orgasm flashed through her, a tiny, humble little thing that nonetheless made me feel extraordinarily proud.

The remarkable thing about Dee Dee Hamilton, when she climaxed, afterward, she was as nonchalant as if she had just sneezed. The bliss suffusing her face made her look ethereal. Her smile was spacey and limpid. She left the car with the coat over one arm and her blouse still open, her bra undone, breasts bare in the moonlight. I watched her disappear into the house.

The next night, I managed to ask her about going into her house semi-nude like that and she merely shrugged as she finished unbuttoning her dress. "My erstwhile mother is gone. I am alone. Who is to see? No one would care. I have to leave the twenty-third to go to my aunt's for Christmas." She sighed. "You, you will not be there to take the edge off." She smiled dreamily. "I think I am beginning to rely on you. After, last night after uh, after, I went right to sleep. That is unusual."

I attended to her breasts that night and each night of the week till Friday. The intervals seemed to focus me because if I hesitated in studying, relaxing my stiff concentration, her breasts appeared in my mind's eye and taunted me. I had to study or I was going to go utterly mad. So I licked and kissed and sucked her breasts each night till the car began to chill. Each time she left the car in some semi-nude version of erotic dishabille. Thursday, she got to the door, turned to look at me, then came back to the car, opened her door and crawled inside on her knees to kiss me rapturously for a long couple minutes. When I began to knead her breasts, she groaned and tore apart from me and fairly ran into the lusciously empty house. My poor cock was utterly neglected and I was, I confess, puzzled and with some small disappointment. She never once made any attempt to reciprocate. That night on the way home, I realized that this would get old, eventually but then smirked at myself because it was certainly not old yet. I was happy to wait.

For all of December, I had neglected the guys. Sammy found me after my last final and I owned up to my sad condition.

"Yeah, Landon said Kyla told him about seeing you with some blond that was not Mrs. Wills." Sammy had been waiting for me and I knew the other guys had sent him. When I was not around, they tended to send Sammy, particularly if they feared repercussions. I could not imagine what they feared from me. Then I realized the guys were just his cover. "Mom, uh, she is wondering what is going on." He laughed but it was a terrible, nervous laugh. "I think she feels neglected. She, she asked me to tell you that she thinks she might have a job for you, after Christmas." Sammy was clearly curious but unwilling to inquire the exact meaning of his message.

"Tell her, tell her okay." I said. Visions of Mrs. Honeywell in various sexual positions and conditions flashed through my mind like movie trailers played at high speed. This was the first sexual thought I had that did not involve Dee Dee's tits in some time. Well, in a week, anyway. "How are the other guys?" I felt a twinge of guilt because Landon had called a couple times and Chris but I never took or returned their calls.

"They are wondering what the hell is going on with you. Chris said something about Double D Hamilton? Say it ain't so, Joe!" Sammy tried to grin.

I did not respond. Then I shrugged. "Sammy, I guess I am in love."

He gawked, then shrugged. "What am I going to tell my poor pining mother?"

I hoped it was rhetorical and treated it so. He waited for a response and I moved on, pretending I missed the implication. My cock, however, still loved the idea of Mrs. Honeywell, well, to tell the truth, by this time, attending to Dee Dee's tits had left my cock somewhat less selective than the rest of me was yet inclined to be. "I'll uh, we should get together after Christmas. It's bowl week." I felt lethargic and my voice conveyed a distinct lack of enthusiasm for getting together with the guys. I feared it. It was like I had a big, perfect snow flake balanced on a cold finger so that it was not melting but I knew it would not last. If I put D. Debra to the test with my guys, the snowflake would evaporate and this euphoria would be gone. I was fucking addicted. The euphoria was intoxicating. I just did not want anyone fucking with it. I had no way to tell anyone that. Funny, though, my sisters seemed to understand instinctively. I had no such hopes that the guys would. What a pussy! And I mean that in both ways!

"We'll, we'll get together next week or something." I just walked away. Sammy stood there staring at my back. I felt it and twisted around to glance back at him and he had the oddest look on his face. It was not till I was on the way to pick up Dee Dee that I realized he looked like I felt several times with the MILFs. Quizzical. That is the word, I felt and Sammy looked quizzical.

Finals were over. Finally. December 22. When I picked up Dee Dee she seemed like a guitar string that was newly loosened. She climbed into the car and immediately leaned over and kissed me soundly on the lips. It was aggressive without being particularly sexual; like a strong statement made by the lips without using words. "Sonny, I could not have done this without you. I mean it! I usually have had someone in my bed during finals but this semester, I determined to do it on my own, cold turkey. I never would have made it without your wonderful lips! I thought Materials was going to kill me and calculus had gotten way difficult." She brightened. "I aced both thought. I am sure of it. So, you done good, kid."

"Does that mean I pass the nipples and me test?" The question did not seem so pathetic as it had the many times I wanted to ask for a copy of my report card. Now it was almost funny. D. Debra did not acknowledge my half-hearted inquiry.

"I usually need to have a man to survive finals. The last two years cock was the only thing that got me through them. But now, you, you my lovely man, you are unique! I know that now. I, I found a happy medium. I know, I know I have not been fair to you. I am not going to be fair to you. I have not said it but when you kiss my tits, you make me want to come so badly, when I finally do, it is luscious beyond telling, beyond words, beyond any ability to make sense of it. I, I have never felt that before." She laughed but it ended up a snorting chortle. "Of course, I never went this long without going to bed with a guy before either. I, I do not understand what you are doing but I," now she looked down and away, "I am going to use you till you say stop." That was all.

She was leaving the next day and so we went to a movie, had a late snack and I took her home. She sat looking at me in the warm car. For that evening the MILF list was forgotten and I felt like a normal college kid chasing pussy. Eager, nervous, eager, eager, anxious. The silence stretched. And stretched. And stretched. She did not move but regarded me with a neutral gaze, barely blinking. Finally she bowed her head. "Sonny, I may be gone a week or two, if Mom..." Her lips tightened into a thin line. "I, I want something from you."

I nodded before I gave any thought to what she was saying. My vocabulary was two words with her; "yes" and "when"?

She looked up at me. I thought she was going to say something but then she slumped lower in the seat. She removed her low heels. She shrugged off her coat. She wore a rough knit dress that clung to her plush body, accenting her curves with the glinting weave of the knit. The skirt was tight, clinging to her thighs and stopping about six inches above her knees. She clearly wore hose. She reached down and gripped the skirt and tore it up the seam along her left thigh. She tore it all the way to the waist.

I did not know what to say and dared not think anything. I watched. I watched while she pulled her skirt up and revealed pantyhose. She pulled the hose down her waist, down her wondrous thighs, to her knees and then rolled it off her feet. I confess, I was trying to catch a glimpse of her pussy but a flap of the destroyed skirt kept her covered. I dared not lean over too far lest I scared this wild woman away once more. Once she was essentially nude from the waist down, she twisted in the seat.

Actually, I thought she was going to fuck me. I did and I was thinking, wondering why she did not invite me into the house. The car was going to prove cramped. I was thinking of taking her on a bed or the floor or against a wall or something when she finally did speak. Turned out I wasn't the one doing the taking.

"Sonny, I know, I know I am unfair. I, I have my reasons. Now, I, I want you to eat me. I want you to suck my pussy, make me come with your tongue and your mouth and lips. Is, uh, is that okay?"

Suddenly she seemed so terribly vulnerable, so uncertain and uneasy with showing me this need of hers, I felt a goushy flush of pleasure flood over me and all I wanted was to do whatever she wanted. I nodded. My mouth got dry and for a moment, I felt terribly fearful about that. There was no need. In the darkness, she began to slump down in the seat. She pulled her legs up and pivoted on her butt and back till she could place a heel on my shoulder. I turned as much as I could but found the steering wheel in the way. I tipped it up and the slide the seat back. I could smell her arousal. It fill the car like perfume or actually, more like a cloudy aphrodisiac. It was a heady blend of pussy and something else. She put hooked her heel on my shoulder and scooted lower in the seat, pulling herself towards me. She placed the other heel on the other shoulder and then slowly slid her legs past my ears. Her skin whispered on my shoulders. My hands went to her calves and I ran my hands first up to her feet and then down, to the calves, to the knees and further, onto the roundness of her full thighs. For the first time I felt the firmness of her body, the lushness of her thighs. My cock snapped hard like a spring returning back into position after being bent out of line.