Tammy Pt. 01

I met the woman meant for me. Teresa was drop dead gorgeous with long, dark hair, full lips, dazzling blue eyes, a body curvy in all the right places, and a sense of humor that always brightened my day. Two dates were loads of fun and we were sexting each other , anticipating our third date. We were both 41 and rather traditional: even though we wanted to rip each other's clothes off the first time we saw each other, we waited until the third date before consummating the relationship. Call us old fashioned.

It was a bright, May afternoon when I got away from my office, and traffic wasn't horrible as I drove across Chicago. Slow, of course, but I know short cuts that keep me off the Ryan at peak hours. My office is near O'Hare but I've got a lovely apartment overlooking the Lake. It was ready for seduction, and my cock was almost bursting my slacks. We'd spent the Saturday afternoon before on the Oak Street beach, soaking up some rare warm weather, and it was tough enough to keep my composure: her body in a gold bikini fueled my wet dreams ever since. It was all I could do not to ravish her right there on the sand, but it probably would have stopped traffic on Lake Shore Drive.

Right after I walked into my pad, Teresa sent me a text message: she was held up until 7:30 at her office. No problem because our reservations were for 8:00, and my planned seduction was after that. I fixed myself a gin and tonic, and settled on my couch to watch the ships on Lake Michigan. It was tough to relax, but if I didn't the date would be far too anxious and we wouldn't have a good time. A cigar would have been a good idea as well, but I didn't want to ruin my breath. Everything had to be perfect this first time we had sex.

Then my doorbell chimed. "Who the hell can that be?" I asked myself. I lived in a building where no one could get access without an access code or a request from the front door I'd have to approve. It could be my buddy Bart: I thought he went to Frankfort on business, but he may have gotten in and stopped by to tell me about his trip. No problem, he'd understand after a couple of Scotchs on the rocks, and it would pass the time. Straightening my collar, I answered it to find a pudgy, freckled red headed teenage: Tammy, Teresa's daughter. "Hi, Mr. Jackson," she said in a tone bordering a sneer.

"Hi, Tammy. This is a surprise."

"I know." I beckoned her to come in, and she strode through the doorway. Teresa introduced me to her 18 year old daughter when I visited their apartment at the beginning of our last date. The product of a teenage marriage, Tammy was almost completely ignored by her redneck father all her life, and she gave her mother an astonishing amount of disrespect. Tammy's skin was very fair and almost universally freckled, her hair was in a short helmet cut, and her nose was a bit large. She was wearing sweat pants that somewhat concealed her thick legs, and a sleeveless pink polka dot blouse over her ample torso. Flip flops revealed unpainted nails roughly groomed. "What brings you here?" I asked. "How the hell did you get in?"

"I came in with a resident, said I was a student from out of town and you were my uncle," the girl began. "People buy all kinds of bullshit like that. You and Mom have a date tonight, and she's really excited about it. You're the hottest thing that's come around for a few years and I'm worried. Are you planning to have sex with her tonight?"

Damn that kid! She must have snooped her mother's cell. I was startled by the bold question, but Teresa had warned me about her. It would be three long months before she went away to college, and her mother found a small liberal arts school in the Bay Area to send her. Teresa's worry was her only child would decide to do all her remaining education online, which would have kept her at home. In the meantime, I would need to deal with her as a potential source of trouble. Weighing my worlds carefully, I responded, "I'm afraid that's none of your business, as is any other part of my relationship with your mother."

"I was afraid you'd say that," she responded, plopping down on my couch with a thud. "I need to talk you out of this somehow. Somebody's gotta protect her, 'specially if it looks too good. You really look too good to be true. There's some interesting stuff I found out about you on the Internet."

"There's nothing on the Internet I'm worried about. I don't even frequent porn sites, and my security rating with the government was the highest possible at my pay grade when I worked at IRS, where my specialty was fraud. I know how to hide anything I want to keep secret from prying eyes, as well as track down any snoopers. If you weren't a kid, I'd say you have more to worry about with uncomfortable secrets than I do."

She snorted. Teresa told me she was a difficult child, always rebellious, without many friends, and uninterested in finding a future for herself. The progeny of a successful parent, her mother thought she was planning to live on her inheritance while keeping busy with various fan clubs and solitary hobbies. A lot of her time was spent with a couple of Internet virtual reality games, mostly WOW. "Well, I have to keep an eye on my mother, make sure she doesn't get tied up with some jerk."

"Has that happened much?" I knew the answer before I heard it.

"Nope. She's been pretty busy working and takin' care of me."

I sat down opposite her and looked at her eyes, trying to unsettle her. She returned my look with a rather blank, icy stare, not disguising her contempt. Without batting an eye, I told her flat out, "You know I make more money than she does, and I assure you I'm not the 'love 'em and leave 'em' type. We enjoy each other's company, and that's all that matters. My hope is we spend some leisure time together, unless that cuts into your personal time with her."

I knew it didn't: Tammy hadn't done much of anything with her mother since she was 12, and Teresa wanted her to get over some of her attitude before improving the relationship. "She needs to do more than grow up a bit," her mother said on our first date, "she needs to care for something else, someone else. The only person that matters to her is the one she sees in the mirror. Why God had to give me such a hateful child is a mystery, I must have done something pretty bad to deserve her."

The hateful child continued giving me a baleful glare, so I tried to get something out of her: "What can I do for you this evening, Tammy?"

"I want you to stop seeing my mother."

"There's nothing you can do about it. I can have you barred from this building, starting tonight, and I can take care of anything you try to set me up for, mental or physical. How much I see of your mother is completely up to me-and her."

She tucked a leg up underneath herself. "Well, I don't want you having sex with her, marrying her and making babies. I'm an only child and I want to stay that way."

"Because you're so perfect already?" The girl stuck out her tongue at me. "Why are you worried about that, you're going to be all right no matter what happens."

"I want Mom's money all to myself. I don't share."

"How old is your mother?"

"36."

"You'll have to put her in a nunnery to be sure that happens, whether it's me or somebody else. She could adopt as well, even by herself, as many children as she wants. You've got no control over that."

"She won't adopt, she says she don't want to adopt any more kids. She likes babies a lot..."

"Probably says she won't adopt because you're around. Is there anything serious you'd like to say before I have security come up her and throw you out for good?"

She licked her lips, and looked down to her left, the first sign of weakness I saw. "What if I jerk you off?" she said quietly.

"Huh?"

"I want to jerk you off, whatever it takes. For all I know you and Mom could get crazy tonight and have a kid. If I can jerk you off now, you won't be able to c-c-cum later. I know I can't stop you from going out, but..."

I almost laughed out loud at her proposition. How did this kid think I'd give up quality sex with a gorgeous woman for an inexperienced hand job from a geeky teen who probably couldn't get any action from the losers at a Sci-Fi convention?

Like some kids, Tammy thought if she watched something instructional on the Internet, she could do it, and Teresa thought Tammy had been watching a lot of porn. "If Tammy offers you anything, feel free to take it. I'm pretty sure she hasn't done anything with anyone, not even the desperate boys in her class want to date her. Some contact with real life would do her some good. I don't care if you make her your sex slave and get her knocked up, it won't affect our relationship."

Little did Tammy know what my capabilities were, and educating her in some reality was an interesting concept. "All right. Do it."

She was startled, as if she didn't expect me to call her bluff. "What?"

"Jerk me off, protect your mother if you want to. All I care about is having a good time, whether it's now or later. You said you'd do whatever it takes, so I'll let you do whatever it takes. Get my dick out."

Suddenly she became very nervous, like she was going to back down. "But-but-but y-you've got to meet Mom at our place pretty soon."

"Your place is five minutes walk away, and the restaurant will hold our reservation indefinitely, if necessary. Do you think it will take an hour and a half to bring me off?"

"No, no, I know better than that." She patted the couch beside her uncertainly. "Come sit over here and we'll see what comes up." It was all I could do to keep from laughing as I sat down next to her as far away as I could. "Aren't you going to take off your pants?"

"What kind of foreplay is that? We're in no hurry. Turn me on, get me aroused. You're a woman now, take the initiative. Show me your seductive moves, babe."

"Ah-ah-ah"

"Of course if you don't, I'll still be horny and ready to pound your Mom good later. It's been long enough, she'd probably like that."

She licked her lips again and left her mouth open, exposing an overbite and crooked teeth. Her hand was shaking as she put it on my knee, and it was clear when she was rubbing my thighs she'd only seen it done, never done it herself. When she worked her hand into my crotch, I will still completely limp. "I thought you'd be hard by now," she said.

"It seems you have some more work to do. Maybe you could do a little dance for me, talk dirty, show me something."

She unbuttoned her blouse awkwardly, and when it came off, I saw a cream colored bra containing pair of huge, flabby tits. Her face got a little bit red, but when she noticed it made no difference in arousing me, she reached around to unhook the garment, her boobs falling forward heavily as they came free. There were a couple of zits on each side, a couple of wisps of hair around her medium sized nipples. She reached out to pull my pants down and I accommodated her, my pecker stirring with a little interest as it came into view. I'm a little under average, but I could tell from her look it as the first one she'd ever seen in the flesh. "Is that how big it is?"

"Well, it could get bigger. Depends how you work it. How big should it be?"

"Ah-ah-ah, I don't know. All the ones I've ever seen before are bigger."

Yeah, right kiddo. Bet I could count all the cocks she'd stroked with one digit. "If size mattered all that much, then natural selection would have taken out every man under eight inches. Anyway, this is about my pleasure, not yours. What are you going to do about it?"

Moving over my crotch, she made a big deal about dropping a big glob of spit on my cock. I winced when she grabbed it too hard, but she took the hint and loosened up. Her rhythm was rather feeble, and ever so often she made a big deal about spitting on it. I got a little harder, but not much.

She gave me a look of confusion, no knowing what to do next. "Maybe you could offer to let me touch you somewhere. Then you could have a little fun, too."

"Like what?"

"How about letting me work on your tits?"

"Oh yeah," she said, as if a connection was finally made. "Touch my tits, they're really big and soft. Suck on the nipples if you want."

I started with brushing the one closest to me, teasing the skin and making her sigh. First I used my fingernails, then my tips, gradually increasing the contact. Her breathing quickened and her eyes got a little glazed. Then I made full palm contact, massaging and squeezing her huge churns, and her eyes closed. In some ways, it was nice to see a young woman get touched for the first time and deal with the new sensations. She responded by jerking me harder, but I had to slow her down because she was almost pulling it off. Then I started working her areolas, making them harden and peak, and milking them gently, making her moan.

Her hand had stopped, and after making sure she was lost in another place, stopped myself. Her eyes popped open and a disbelieving look crossed her face: "What? Why didya stop?" she asked in a quiet, disbelieving tone.

"Why did you? This is a two way street, sweetheart. This is about making me happy, right? Otherwise, I'm fucking your mom later."

"Oh right, yeah. I gotta make you cum." She started stroking me again, almost pulling the damn thing off. I made her slow, and it wasn't very stimulating.

"This isn't working, you'll have to do something else."

Her face was blank. "Ah, really? Oh, ah, like what?"

"You'll have to suck it. You've done given head before, right?"

She was a little confused, and I gave her breast another light brush to keep her that way. "Ah, yeah, sure, no problem. I like sucking cock. I want to suck your cock." She started pulling off her sweat pants, revealing white panties, which was on the floor shortly. Her butt was huge, an ocean of freckles with a hit of cellulite starting. She headed straight for my dick, popping it into her mouth without prelude.

"Be careful with your teeth, Sweetheart. And lick my balls once in a while."

Once again, it was clear she'd only watched videos of this and never done it herself. Within a minute, she seemed to start enjoying it, which I attributed to the fresh pineapple I'd eaten as an afternoon snack the past few days. I reached down to play with the side of her breast, and she purred. I felt a sharp edge on my cock occasionally, but it wasn't bad and I took it as living dangerously, which helped me get excited.

She was short enough I could reach down and touch her ass, which made her groan and quiver. I could have reached between her legs and played with her pussy, but I wanted to save something and didn't want to distract her more or she might go too far with her teeth. A familiar feeling started building in my balls, so I pulled her head off. "I'm about to shoot my wad. You need to swallow it."

"Really?" The lights were on, but no one was home. Then she woke up a little bit. "No, not really. Not if you're going to put a big load in there. How much you gonna cum?"

"I don't know, depends. Don't you usually swallow? Are you a rude girl who spits it out when a guy comes in your mouth? Or do you like facials?"

Shaking her head. "Ah, no. I always swallow the guys I like. Why are you special? Why should I swallow you?"

"Well, if you don't make me completely happy, I might not let you do this on my next date with your Mom, and that means..."

Another switch flipped. "Yeah, I'll swallow it. Tastes pretty good anyway."

"Make sure you stroke me with one hand and play with my balls with the other." I congratulated myself because she did what she was told, and soon I filled her mouth to overflowing: she even licked up the bits that oozed out of her mouth. It felt wonderful. I had to pull her off because she didn't stop sucking and she was pulling her lips off her teeth.

"All right, young lady. You've done your work tonight. Get dressed and get out. Now!"

Tammy gave me a strange look, but put her clothes back on without a word, and started for the door. Sure, it was pretty cold, but this was reality training: the world is a pretty cold place. Before she got there, I stopped her, "You have your deal for tonight, I won't be able to have sex with your Mom. The next time, though, may be a different story."

"I want her money all for myself. I'll do it again. I'll do what I have to."

"Next time I'll come early to your house. You can do it there."

"All right."

The date was one of the most fabulously romantic dinners I've ever had at the top of Hancock building, and Teresa and I did more than fuck like rabbits that night, we bonded. She didn't get home until daybreak.