Try as a might. I just couldn't settle myself. I was shaking all over - just sitting there in the car with my heart pounding - trying to convince myself of the reality of what had just happened. Then, the chime of my phone snapped me out of my state for a moment. Recognizing the number, I picked up immediately - hearing her now-familiar voice.
"You can't tell anyone about what we did."
I had known for a while that dating Tiffany was a bad idea. She was so immature emotionally. Despite being the same age as me, she was just a kid . . . on the inside. But, on the outside she was FAR from a kid. Her looks and her curves made her prize of the school. And, I always get first prize.
We had fun at times, but having just turned 18 and finishing my senior year of high school, I was looking for more than fun. Most of my friends were getting into all sorts of mischief with their girlfriends. Some of the stories they told were straight out of porn movies.
They may have been lying their asses off, but their lies were a hell of a lot better than my reality. I was getting nothing. Tiffany would hardly allow me to touch her much less come close to anything that resembled sex. So when my frustration hit it's peak last night after getting just one handful of tit over the bra, I figured that was it for Tiffany and I.
I was willing to do an awful lot to get my dick wet - whine, beg or otherwise. We'd had the discussion many times. She wasn't ready. Sure I was frustrated, but I am no asshole or violent rapist. I wasn't going to force anything.
Although, I wasn't going to sit around and wait for her either, and when I told her that it was time for me to move on to someone more mature, I think it was pretty clear to her that I was looking for a girlfriend who would put out.
That wasn't even 24 hours ago. Man, what a wild day.
I woke up this morning with all sorts of thoughts in my head. Was I making a mistake? I really did like her a lot. We enjoyed each other's company, and other than me going home every night with blue balls, we always had a great time. Plus, she was SMOKING hot. Nice tits, tight ass, trim waist. She had it all going on from head to toe.
By lunch time I had moved on from those thoughts to wondering who I might ask out this weekend who would be the most likely to blow me on the first date. I'd heard stories. It wasn't completely beyond comprehension.
So when my phone rang and I looked at the number, I almost didn't answer it. It was Tiffany's house. But, It was a little odd as she usually called from her cell. Maybe she wanted to arrange the exchange of personal items? Even better, maybe she'd decided to give me what I wanted!
"Bobby?" It sounded like Tiffany, but in just a moment I knew it wasn't. "Ms. Lipton? . . . Oh . . ah . . . yea, this is Bobby." This was pretty weird. Tiffany and I had been dating for almost a year, and Ms. Lipton had never called me. I didn't even know she had my number. Plus, she wasn't exactly the chatty type. It was just her and Tiffany at home, and most of the time - if she was there - she was in her room reading or working in the flower beds. She wasn't unfriendly by any means but hardly one to strike up a conversation with me.
"Hey Bobby. I . . I heard you and Tiff are having some problems."
"Yea, we sort of broke up last night." I would have thought Tiffany would have told her as much. She always spoke as if she shared most everything with her mom.
"Yes. Tiffany told me about it this morning. I'm really sorry to hear that. Are you sure that's a good idea? I mean you guys have been together all year, and with prom coming up and all?
I'd hate to see your last few weeks of high school get all screwed up over this . . . Hey, Bobby? I think we should talk more about this. Can you stop by this evening?"
I didn't even really notice that Tiffany's car was gone from the driveway when I pulled up to the house. I'd been there dozens of times. It was almost automatic as I walked to the door and rang the bell. Surprisingly, Ms. Lipton answered the door. I wasn't expecting that.
"Hey Bobby. Come on in." As I walked past her, I couldn't help but catch a whiff of an extremely wonderful perfume. I'd never noticed that before.
"Tiff is not here. She went out with some of her girlfriends. I hope they can cheer her up after all that has happened. She's really upset about this."
Immediately, there was an awkward tension in the room. Being alone with a woman 25 years older than you is odd enough, but there was more going on. Why was she wearing that dress? Those heels?
Until just then, I had never even really noticed how much he looked like Tiffany - or more I appropriately, I guess - that Tiffany looked like her. They were essentially the same woman. They were the same height, the same shape, the same eyes, same hair. Only the effects of time seemed to distinguish them. Ms. Lipton had probably added a few pounds over the years, but as fortune would have it, they seemed to have landed in all the right places.
She had taken her seat in the chair sitting 90 degrees to the sofa I sat on. She was within arms reach of me making the scent of that perfume easily distinguishable. As I sat there, I couldn't keep my mind from wandering. What the hell is doing on? I still had no clue when her voice broke the awkward silence.
"Tiffany told me why you guys broke up."
Oh shit. I'm about to get my ass chewed by some lady just because I want to get laid. What the hell!
"You need to understand that it's harder for some girls to become comfortable with certain things, Bobby . . . But, I also understand your point of view. Young men have certain needs that can't be ignored."
This conversation was going from awkward to surreal. As I sat there looking down and trying to figure an excuse to leave, I felt her hand touch my thigh. Looking up, I never made it to her eyes. All I saw was the plunging cleavage from her strapless summer dress as she bent to reach me.
"Bobby. I want to do all I can to make my daughter happy. She wants to be with you. I think I also have a pretty good idea of what you want as well. It sure seems like we could figure something out that worked for everyone."
As she finished speaking, Ms. Lipton slipped from the chair to her knees in front of me giving me an even better, unobstructed view down her dress. As I looked up at her face, I could tell that she knew exactly what I was looking at. She simply smiled as she placed her hands on each thigh and spread my legs to make herself a place to move closer.
I may not be the sharpest knife in the drawer, but by this point, I think I had at least some idea of what she had in mind. So, I didn't hesitate to respond when she spoke. "Stand up, Bobby."
Her eyes never lost contact with mine as she unbuckled my belt, unfastened my jeans and pulled them below my knees. When she did break contact, her focus went straight to the tent formed in my boxers. Grasping each leg cuff, it only took a gentle tug to free me. She stared at it for a few moments as if she was contemplating her next move. Maybe she was simply mustering the final nerve need to go through with her plan. Then gently placing her hand on my stomach, she gave a slight push and simply said "sit."
Ms. Lipton gently massaged my thighs as she inched her face closer and closer to my crotch. As she got within a few inches, it was if she appeared to be almost hypnotized - her nostrils flaring as she deeply inhaled the essence of my maleness. Finally, her lips begin to gently touch my balls and the base of my shaft. Finally, she allowed her lips to part and her tongue to begin to taste her prize.
All I was really hoping for was that I got my cock in her mouth for a few seconds before I came all over the place. I was going fucking nuts. This was the most amazing experience of my life.
Once she began to use the flat of her tongue along the underside of my shaft, I really started getting bent out of shape. When she reached the tip, I couldn't help but notice her reaction to the fluid that had already begun to leak from my cock. She REALLY liked it. Locking her lips around the head of shaft, she swirled her tongue all around to gather as much of it as she was able, and then for good measure, she sucked hard - drawing all she could from the opening.
That taste must have been her cue to move along with things, and in one motion she opened her mouth and swallowed down as much of my dick as she could stuff into her face.
I had imagined for the longest what it would feel like to get a blow job, and Ms. Lipton was going WELL beyond my imagination. It was amazing - blissful - blissfully amazing. As she worked my cock in and out her mouth, her tongue seemed to find every sensory point. There was no way in hell this was going to last as long as it should.
I really wanted to sit there and get my cock sucked like a good boy. I really did. But, there are certain instincts that are extremely difficult to overcome. At some point, the most basic urge to cum cannot be unbridled. After only a minute or two of her efforts, my hands had found her head and my hips had begun to return each of her lunges. In no time at all, I had a nicely established rhythm fucking my cock in and out of her mouth. As some point, Ms. Lipton had the wherewithal to wrap her fist around the base of my shaft - probably to keep me from shoving it too far down her throat. But, when she began to use it along with her mouth, my fate was written.
I think I had probably beat off at least 1,000 times before this day. So, I was fully aware of what was to come (so to speak! :) ) But, my more recent experiences with spanking it were that it was a slow and deliberate build to the climax. This time, it didn't quite work out like that. My orgasm came upon me in a sudden and overwhelming way, and with little more warning than an inaudible grunt, my hips lunged as I began ejaculating into her mouth.
Ms. Lipton's reaction was some combination of startled surprise and a giggle - sort of a squeak really. Her mouth was filled with spunk almost immediately. But as burst after burst of my load spilled into her mouth, she never stopped working on my dick. Her hands and mouth worked faster and harder to match pace with pumping hips. I could feel her throat contracting around the tip of my cock as she swallowed - all the while keeping a tight seal around my shaft so as to not waste a drop.
Sensing I was spent, she slowed her pace but kept a light suction on my cock to make sure there were no remains of my load. When it finally popped from her mouth, there was no trace of cum anywhere. She had taken every morsel.
The aftershock of my orgasm was still very much present, but at least I was starting to regain my senses. So, when she stood and lifted my hand, I was aware enough know to stand as well. As I arose, she turned her back to me.
"Help me with my dress, Robby."
Fortunately, the ridiculously massive load of cum Ms. Lipton had sucked from my balls had taken the edge off somewhat. I was reasonably composed as I found the tab of her zipper. Lowering it down, I saw nothing underneath but her smooth skin, and as it fully unzipped, the dress just fell to the floor.
My eyes drank in her curves from her neck on down. Only a thin, lacy pair of panties covered just the top of her ass cheeks. They were a little more than a g-string, but not much. My hands had found her hips and just rested there. I guess I was so enamored with what I was seeing that it never occurred that I was allowed to touch. Maybe I was just scared.
Whatever it was, Ms. Lipton was not willing to wait me out. Placing her hand over mine, she began to guide them around her waist and up to her breasts. My heart began once again to race as I held them and felt their heft. They were so, so soft. There's just nothing else that feels like that.
Obviously, I was excited, but it seemed she was starting to get there as well. Ms. Lipton began to moan ever so softly as her hands guided mine on a most delightful tour of her body. Finally, she pushed me southward past her waist, and with her open hand aligned with mine, she "forced" me to her crotch allowing to feel her wetness as if she was masturbating with someone else's fingers.
She was giving me a quite detailed lesson on how to pleasure a woman with your fingers. It wasn't long at all, and she had guided me to the little button at the top of the slit and began to massage. Using her own hand to lead, Ms. Lipton perfectly demonstrated how to circle the clit and vary the pressure, and how to dip down into her slit on occasion for a bit of lubricant to aid the process. As she became more and more exciting, she began to grind her ass into my crotch. My cock had long sense returned to full mast, and it had found a nearly perfect resting place between her ass cheeks.
It only took the slightest separation and Ms. Lipton's other hand was able to reach between us and find my cock. Pointing it forward, she again moved closer to me. Only this time, the tip of my shaft was aligned just as she wanted it, and it easily slipped into her opening. As soon as she seemed confident she had found her mark, her hips trust back into me, and I was balls deep in her cunt.
The position was a bit awkward actually. She wasn't about to let me take my fingers off her clit, and so as I hunched over her, our love-making became more of a grind than a pump. It was probably better actually, as it somewhat prevented me from spending my second load as quickly as I had spent the first.
Ms Lipton's breathing began to grow more rapid, and she began to dig her nails into my hand - forcing me to increase the pace and pressure on her clit. She was well on her way to a powerful orgasm. I was just hoping I could outlast her. Despite having blown my nut just a few minutes ago, I was already beginning to feel another rising. Fortunately, her's arrived first. Her cunt had become so slick it took a bit of effort just to stay attached to her. So, when she started to cum, I simply buried my dick as deep as could and held he to me as she erupted.
The feeling of her walls contracting around my shaft was unlikely anything I had ever felt in my life. It was simply indescribable. And, it lasted for far, far longer than my orgasms ever had. She came for what seemed like minutes although surely it was not. When she finally began to come down from her high, I had reached the point that I was ready and wanting to find my own as quickly as possible.
Without ever allowing my dick to slip from her, she turned slightly and bent over the same chair where she had sat and lifted one foot up to the seat to further open herself to me. For the first time since I had entered her, she spoke.
"Fuck me, Bobby . . . hard."
She was so wet, it took no effort at all to gain my rhythm quickly. In just a few strokes, I was working the full length of my cock in and out of her. Looking down, I could she my shaft was coated in her whitish fluids. It was so heavy it was covering much of my crotch and public area. My hairs were even matted down. It was a glorious sight.
As my pace quickened, I fulled expected myself to cum at any moment, but for some reason, I could not. The pleasure just continued to rise as a more and more rapidly plunged myself in and out of her. I HAD to cum, but I couldn't get it out.
Grabbing her hips, she became hardly more than a means to my release. I pounded into with all of the speed and energy I could summon. Her gorgeous, round ass was the perfect defense for my onslaught. The fleshly cheeks took each blow of my own hips with an audible slap as I banged against them. I was fucking her as hard and fast as possibly could - solely focused on my release.
And then it came. Oh, did it come!!!! With a final furious heave, I buried myself as deeply into her as could and held her there as I emptied into her cunt. My blasts seemed so strong that surely she could feel them splattering against her insides. I could say nothing - only grunts and a then few whimpers as the wave of bliss faded.
Ms. Lipton seemed none the worse for the wear. I was actually a little impressed that she so readily took my pounding. Within a minute or so, she was mostly back down to normal. She seemed a little more energetic, but otherwise she was the same as when I walked in the door.
"You should probably get going, Bobby. I'm not sure when to expect Tiffany."
So I hastily dressed and straightened myself as much as I could. As I was leaving, she didn't say anything else at all - only giving me a sweet - almost motherly - peck on the check as I headed out the door.
I am not even sure my feet ever even touched the walkway as I headed to my car. I may have floated. And, when when I finally there, got then door opened and sat down inside, I just couldn't settle myself. I was shaking all over - just sitting there in the car with my heart pounding - trying to convince myself of the reality of what had just happened.
Then, the chime of my phone snapped me out of my state for a moment. Recognizing the number, I picked up immediately - hearing Ms. Lipton's now-familiar voice.
"You can't tell anyone about what we did . . . "
"If you want to do it again."