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!
"Hello."
"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.