Learning From Tammy Ch. 01

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He has his first date with Tammy.
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Part 1 of the 4 part series

Updated 09/29/2022
Created 01/03/2006
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Chapter 1 – The date

Just over a year after my divorce, I moved to St. Paul, to work for a national insurance company in their risk management department dealing with insurance fraud. The divorce occurred for many of the typical reasons, not communicating effectively, arguments over her spending habits, leaving my shoes in the living room every night – you get the picture. And although we never fought about it, I was never overly happy with our sex life. My ex-wife just wasn't very adventurous in bed. She enjoyed receiving pleasure, and enjoyed receiving it in many different ways, but she wasn't very creative in giving pleasure. I always made sure she was satisfied, and she was multi-orgasmic – if you just paused for a couple of seconds after she climaxed, just a little stimulation would take her over the top again and again. But all too often I came away feeling unappreciated and un-satisfied.

My ex enjoyed a little anal play, you know, having a finger or two in her ass when I would go down on her, yet she wasn't at all interested in anal sex. She enjoyed having me eat her pussy almost anywhere in the house, kitchen counter, the sofa, on the pool table, yet she rarely spent more than a few minutes sucking my cock, even though I kept myself very clean. As soon as it was hard, she wanted me to "stick it in" her, and that usually was in the missionary position.

Any way, when I moved to the Twin Cities, I figured I would take my time looking for the right woman. I wanted someone who was a little more creative in the bedroom than my ex-wife. Little did I realize the surprise fate had in store for me.

After 10-years of marriage and nearly another year divorced, it had been a long time since I'd 'dated,' and I was having a hard time meeting women and even more trouble asking them out. Several of the women I met and talked to at various places (and who weren't wearing wedding rings) turned out to be "in committed relationships" or "already seeing someone," so I was striking out left and right. It was a little frustrating because I'm not a bad looking guy, 6' 3" – 225lbs. Yeah, I could stand to lose 15lbs, and I could tone up a little, but I'm no Budweiser gut, couch potato either.

After spending a few weeks getting settled into a cluster home I bought in Woodbury, I desperately needed a haircut. It had been nearly 7 weeks since my last haircut and my hair was looking pretty shaggy. I like to go every 4 – 5 weeks to keep everything looking nice and trim. So, Saturday morning I stopped into a local salon in Woodbury to see if I could get an appointment. The girl at the desk quickly replied that she had an immediate opening due to a cancellation. As she stood up I realized she was fairly tall – about 5' 10". She had a nice figure, medium sized breasts, I was guessing her dress size at about an 8 – 10. She was very pretty, with shoulder length, light brown hair that sort of had an auburn tint to it.

"That's great," I said, "I was hoping you wouldn't have a waiting list today."

"Hi, my name's Tammy. Follow me back to my station," she replied.

I introduced myself, "Hi, I'm Greg," I said. We made the normal chit chat about how I wanted my hair cut, what was my normal morning routine when it comes to styling it, did I use mousse or gel, you get the picture. At one point I commented on her lack of a wedding ring.

"Oh, I just haven't found the right guy, I guess," was her reply.

I started teasing her about why an attractive woman like her wasn't seeing someone. We laughed and cut up because she noticed my wedding ring groove hadn't completely gone away yet. She started busting my chops about being married and trying to get a little something going on the side. I told her I wasn't to both questions. It was about this point that I noticed that when she was cutting the hair on the top of my head, she was rubbing the crotch of her jeans on my shoulder. Soon she was done cutting and blowing my hair dry. I put my glasses on and looked in the mirror – boy was I pleased. Tammy was pleased as well, admiring her handy work, brushing away a stray hair here and there.

After she was done, I followed her up to the front desk where I pulled out my money to pay the bill. Mustering all the guts I had at that moment, I asked, "Could I see you again?"

"Sure," she said, "do you want to make an appointment for 4 or 5 weeks?"

"No, I meant tonight; for dinner, or maybe a movie, or even dancing?"

"Look," she said with an expression of consolation on her face, "you seem like a real nice guy. But I barely know you. It's obvious from your accent that you're from out of town. How do I know you're not an ax murderer?"

Not willing to give up at this point, I said, "Look, you can come by my house to pick me up. You can see where I live. You can see that I'm not married. Here, take my business card – call my office. Obviously I'm not there, but you'll know that I'm not lying about whom I work for. Ask the switchboard to drop you into my voice mail. I'm just a normal guy . . ."

"OK, stop," she said. "Is this your cell number on here," she asked pointing to the card?

"Yes," I replied.

"I'll think about it, and I'll call you later. OK?"

"That's all I can ask for," I said.

I left her with $25.00 for a $21.00 haircut and headed out to my Jeep. All the way home I was telling myself she's not going to call, I'd blown it, I should have waited a few visits before asking her out – let her get comfortable with me. You know, the usual self-inflicted criticism we heap on ourselves when we think we've screwed up a good thing. I stopped at Cub on the way home to get some groceries figuring I needed something defrosted to make for dinner.

When I got home there was a message on my machine. It was Tammy. "You forgot to make another appointment before you left, so I penciled you in for 4-weeks from next Tuesday at 4 o'clock. It's all I've got that week because of it being prom season. If you can't make it, call me. And if you still want to get together for dinner tonight, meet me at Applebee's at 7:30." Click.

That's terrific. I was definitely thrilled. Then I wondered - how did she get my home number? It's not on my business card, and I'm too new in town to be listed in the phone directory. Maybe she got it from the switchboard operator, but the operator isn't supposed to give out home numbers. Oh well, I guess I'll have to ask her about that sometime.

All afternoon, I was excited. I took a shower, got dressed and headed over to Applebee's at the appointed time. Tammy was already there. Looking very nice, I might add – tan slacks, a white cotton tank top with her bra strap peeking out the side, carrying a reddish plaid jacket and wearing leather strap sandals on her feet. Her legs are really long, the kind that go from here to there and back again.; and she's got that perfect little space right at the top of her thighs. We had a drink at the bar and made small talk while we waited for our table, slowly drifting into a nice comfortable conversation. The blinking LED pager startled us when went off, letting us know our table was ready. Tammy let out a big laugh, I paid the bar bill, and we were off to our table. The hostess put us at one of the corner booths, so we each slid around our respective sides of the booth until we were sitting on an angle next to each other.

All through dinner we were caught up in the moment. We spent a lot of time staring into each other's eyes. She asked about my divorce, and she told me about her failed romances. We both skipped dessert, and after the waiter went away with my credit card to pay for dinner, Tammy took my hand and said, "Look, you need to really be someone special for this to work. If we're going to get involved, I have a few ground rules I want to lay out. First, I don't expect you to pay for everything when we're together, dinner, movies, and what not. I earn a decent living and when I offer to pay, you just say 'Thank you' and we'll get along fine. Second, I expect complete fidelity if we're going to sleep together. I won't tolerate a man who disrespects the woman he's with by cheating on her. Third, I prefer to have sex in my own bed. Women are like that – I don't know why – so don't expect me to stay over at your house unless I feel real comfortable. That doesn't mean that I don't like to do new things and get wild from time to time, I just want to be comfortable with my surroundings. Last, but certainly not least, I want to be on top."

"OK," was all I could say. It wasn't that I was put off by her conditions, as much as I was surprised by her directness. It was actually quite refreshing. As we left the restaurant holding hands, Tammy reached up and kissed me and told me to follow her home. "I've got the white Honda Civic over there," she pointed.

I followed her a short distance to her home. We pulled up to a nice brick-front split-foyer home in a quiet neighborhood off Queen Street. When we got inside the door, she kissed me again.

"Take off your shoes," she said (a common practice in Minnesota), "Come on up and make yourself comfortable in the living room." "You want a beer," she asked as I heard the tops popping off two bottles without having a chance to answer, "And hey, turn on the stereo."

I did, and an Alan Jackson tune was playing on the local country station. I sat on the sofa. Tammy came in from the kitchen, set the beers on the coffee table, and slipped off her plaid jacket. Throwing it on the ottoman, she picked up the beers, and handed me one as she kneeled on the sofa straddling my legs as she sat on my knees facing me.

I took a sip of the beer. "So you like to being on top, huh," I asked?

"Yes, it generally gets to be a bone of contention with most of the men I've met," Tammy replied. "I really like you, I hope that's not going to be an issue for us?"

"No, I spent the last 10 years or so in the missionary position. I'm sure I can spend a few on my back. It will be a nice change of pace."

Tammy kissed me tenderly and as we parted lips she said quietly, "What makes you think your going to be on your back all the time."

She kissed me again, more passionate this time. After dozens of lingering kisses and heavy breathing, we were soon in the middle of a clothing tornado. Shirts and socks; bras and pants; clothing was flying everywhere. All while trying to maintain the most passionate kisses I've ever felt.

Sitting on my lap again, Tammy started kissing my neck and sucking and biting my nipples. No woman had ever focused on my nipples before and it was thrilling. It seemed the more excited I got, the harder she bit – maybe it was the other way around. Tammy slid off the sofa onto the floor. As she did she slipped down the front waistband of my briefs exposing my hard cock. In a flash she had my dick in her mouth, and the feeling was incredible. She licked, and sucked, and even nibbled a little to intensify the pleasure. My dick isn't huge, a little more than 7½ inches long when erect, but it is fairly thick. Watching my cock slide in and out of her mouth, my head was spinning. She was taking it all the way down to the root – I could feel the head slide into her throat each time she went down. It had been more than a year since I'd been with a woman, and I wasn't going to last much longer.

"Tammy, stop, I'm not going to last much...ooooohhhaaa," I let out a long moan as I exploded in her mouth. I was dizzy. My face felt tingly and numb. I think that was one of the most intense orgasms I had experienced up until that point in my life. Tammy swallowed every spurt and licked me clean; my body twitched every time she touched the head of my cock. Soon she was snuggled up next to me with her head on my chest as I caught my breath.

"I'm sorry," I said.

"Sorry about what? If you were being honest at dinner, then I knew you wouldn't last too long. Besides, we have the rest of the night. You aren't going to poop out on me are you?"

"No, not at all," I said trying to sound reassuring. "I just didn't want you to get the wrong impression. I'm not normally a 2 minute guy," I said sheepishly. Lifting her head in my hands, "Come here, let me try to give you that much pleasure." I said and I kissed her long and hard, our tongues intertwining, I'm sure I could taste my cum in her mouth.

Tammy broke the embrace; she stood up, took my hand and led me down the hall to the bedroom. She pushed me backwards on the bed.

"I want to go down on you," I said. "I want pleasure you, and make you feel the way you've made me feel. I want you to cum long and hard."

Grabbing Tammy's hand, I pulled her down next to me on the bed and kissed her. Slowly and tenderly I kissed her neck and shoulders. As I slowly kissed my way down the center of her chest, deliberately paying little attention to her erect nipples, as I gave them a flick of my tongue, she let out a low moan. I kissed my way down her stomach, while at the same time I used my hand to caressed my way up the inside of her thigh. As I reached the elastic of her panty, Tammy stopped me and said, "Remember, I get to be on top."

As she said this she rolled me on to my back and in one quick motion straddled my face, bringing her fragrant bush just inches from my nose. Her panty was soaked, and as I pulled the cotton between my lips I could smell the sweet aroma of her sexuality. I pulled the panty to one side and slipped a finger into her warm vagina. She let out a soft moan of encouragement as I began to lick the outer folds of her pussy. She had a trim little bush of the same auburn-tinted brown hair. In parting the lips of her pussy, I found the largest clitoris I've ever seen. It was easily the size of the last digit of my pinky finger. I found it was very sensitive as well. I rolled my tongue around it the way a kid does to an ice cream cone. I gently pulled it between my lips and alternated sucking on it and pushing it out of my mouth. I licked it and pulled it in again. All the while, Tammy's breathing is rapidly increasing. "Oh, yeah baby, that's nice," she moaned. As I reach up to her firm breast I found that the nipple that I thought was erect before, is now more than ½" long. I begin caressing her nipples, alternately, with my right hand, while two fingers of my left hand are buried in her pussy, as I'm trying to suck on her beautiful clit, which seems to be getting ever so slightly longer, easily reaching well more than one inch in length. After a few minutes I'm forced to pull my fingers out of he pussy and use my hands to support her ass as she is just grinding away at my face with her pussy. As she starts pulling my head closer, it that were possible, I looked up to see her head rolling back from side to side as she reached a point from where there is no turning back.

From Tammy's parted lips there is a low, deep, moan coming from somewhere inside her. At the same time she's screaming, "Put your fingers in my ass, fuck my ass with your fingers!" I'm sucking her clit, there is a slurping sound coming from her pussy, she's screaming as I'm shoving two fingers, still covered with her juices, into her ass. In what seems like just seconds, Tammy has crossed over, and is almost howling as her first orgasm rips through her. Fluid gushes from her pussy, and I'm licking and sucking for all I am worth, drowning in her ecstasy. This seems to last for nearly a minute; then everything is quiet. Tammy's quiet, her hips have stopped moving, her body occasionally twitches and she catches her breath, I let my fingers slip from her ass. Pursing my lips, I blew my breath over her pussy. She is quiet.

I waited a few short moments; then I decided to see if she could handle multiple orgasms. I stuck my tongue out and touched her clit. She jumped; it was as though I had given her an electric shock. She tried to pull away, but I put my hands on her waist and held he over me. I started licking her clit faster and faster, within seconds she was coming again, and a third time, finally she collapsed and slid down on to my chest to where I all I could lick was her naval. While she lay there on top of my face recovering from her pleasure, it gave me a weird feeling of satisfaction I'd never had with my ex.

After 5 or 6 minutes, I rolled her onto her side and got on top of her. I started to go down on her again, but she pushed me away. "No, stop, I have to pee," she said. So I took her by the hand and walked her into the bathroom. She wobbled as she made her way to the bathroom. As she sat on the toilet, I sat on the edge of the tub next to her and put my hand down between her legs a gently rubbed her clit.

I kissed her shoulder. "Go ahead, pee," I said, as I rubbed her pussy and brought her to another orgasm; her pee flowing over my hand as she climaxed.

As she sat, slumped on the toilet enjoying the afterglow of her fourth orgasm of the evening, I washed my hands and face, and went into the kitchen. I rummaged around and found the fixings for two cups of tea.

"Do you like sugar in your tea," I called.

"No, plain is fine for me," she weakly hollered back.

When I got back to the bedroom, she was laying on the bed in somewhat of a stupor, she said, "that was wonderful. I've never had a man do that for me before. Are you some kind of a gigolo? Where did you learn that?"

"No," I said, "I not a gigolo. In fact, you're only the 5th woman I've ever been to bed with. I do like to read articles about pleasuring women though. Any way, I'm glad it felt so nice for you."

"Nice, it was fabulous!"

"Well, anyway, that thing in the bathroom, I was just going with the flow, no pun intended," I chuckled; "Well maybe it was intended." Tammy just laughed.

As we sipped our tea, I got up to set my cup on the dresser. Tammy set her teacup on the nightstand. "Come here, love," she cooed and patted the bed next to where she was sitting.

I came over and sat next to her. She put an arm around me and kissed me, and dipped me at the same time cradling me in her arm. In one motion she laid me back on the bed and climbed on top of me at the same time. Tammy started kissing me on my neck and my chest. She slowly worked her way down my stomach. Coming back up she licked and sucked on my nipples. That sent ripples of excitement through me.How come I didn't know my nipples were so sensitive before now,' I wondered? Tammy whispered in my ear, "do you trust me?"

I looked in her eyes, as she repeated, "do you trust me? Do you trust me when I tell you that I won't do anything to you that will cause you pain?"

Caught off guard by the question, I knew up until then that she hadn't given me anything but pleasure. "Yes, Tammy, I trust that you won't hurt me."

"Close your eyes, go on, and close them?" I did as she asked. She kissed her way down the length of my right arm to my wrist. Click. I felt something metal on my wrist, and my eyes shot wide open. My wrist is in a handcuff. Tammy patted my chest and repeated softly, "Do you trust me? I promise I won't cause you any pain." 'No pain - isn't that what the Vet tells you right before he puts your dog to sleep,' I thought? I was feeling powerless, and a little nervous. The movie, Basic Instinct, kept running through my head. In response to her question, I just nodded my head yes. "Then close your eyes, and enjoy what you feel," Tammy whispered.

I closed my eyes, as Tammy lifted my arm toward the headboard. Click. The other end of the handcuff was secure around the bedpost. Tammy rolled over me to my left side and secured my left arm as she had the first. Then she was gone for a few minutes. I kept my eyes closed hoping that what they say is true about your hearing becoming more acute when your eyes are closed, but I couldn't hear her. Suddenly there was a shock, but not a shock, just a touch of something cold on my left nipple. "I could have blindfolded you, but it shows much more trust if your willing to submit and voluntarily keep you eyes closed," she said quietly. "Stick out your tongue." I did, and something was pushed onto the tip of it. 'What is that? The taste is familiar. It's a strawberry!' "Let it slide into your mouth, suck on it, chew it slowly, feel the burst of flavor and juice fill your mouth," she said.

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