Learning From Tammy Ch. 04

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This is a continuation of the story of my relationship with Tammy. If you haven’t read the previous chapters, then you may wish to do so to become familiar with the characters in the story. I hope you enjoy the story.

Chapter 4 – Fun in Madison

Tammy slowly fucked my hard cock with her ass as we kissed each other passionately. After a short while, we changed positions and Tammy had me fuck her ass from behind as she lay on the bed with her hips propped up on a couple of pillows. This was the first time Tammy ever let me really control the thrusts during our lovemaking – up until now she was always on top. Maybe it was her way of showing me she was truly sorry, and even though I should have jackhammer’d her ass for all of the B.S. the other night, I didn’t take advantage of the situation. I went slow and took my time, reaching down to rub her clitoris as I made love to her ass. I tried to time my climax to match hers, but she came a minute or two before me. Clenching her abdominal muscles during her orgasm was all I needed to push me over the edge and I exploded deep in her tight ass, collapsing on top of her.

Satisfied, my softening cock slipped out of her ass. Tammy went to sleep right there, sideways across the bed with the pillow under her hips. I grabbed another pillow and lay beside her as I pulled the sheet over top of us and dozed off.

The morning light bought loving kisses and, after using a washcloth to clean my dick, another fantastic blow job from Tammy. I tried to get her on top of me in a 69, but she said she wanted to wait. Before Tammy’s jaw started to ache, I asked her to stop; as good as it felt, I didn’t think I was going to cum any time soon. I was pretty well satiated from the wee hours of the morning.

Tammy whipped up some bacon and scrambled eggs while I took a shower. I told her about needing to drive down to Madison that afternoon for a meeting on Monday, and I asked her if she wanted to come along. It didn’t take much convincing for her to agree to go after I told her about the hotel room I reserved. Her only caveat to the trip being that I had to have her back in Woodbury by 10 o’clock Tuesday morning so she could go to work. I assured her that we would be home on Monday evening. We both agreed that the 4½ hour ride down the interstate would give us the opportunity to talk and get to know one another better. After breakfast, I drove Tammy over to the salon so she could pick up her car.

I kissed her goodbye as she started to unbuckle her seatbelt. “Pick you up at 1:30, OK?” She nodded. I grabbed her hand as she was getting out, “bring some of your toys, and some bath oil beads if you have them.” She smiled a coy little smile.


During the drive down to Madison we talked about the usual things new couples talk about – favorite movies, favorite books, favorite restaurants, worst restaurants, TV, sports teams, bands, music styles, etc. It seemed to me that we were really compatible in a lot of ways. At one point during the drive I reached over and put my hand on Tammy’s thigh. She caught her breath as I did so, and it was obvious, even through her jeans, that she got goose bumps from my touch. I gently ran my hand up and down her thigh, occasionally rubbing the crotch of her jeans. We were starting to talk dirty and I was telling her about all the things I’d like to do to her when we got to the hotel. First a nice bath and massage, while enjoying the bubbles in the large Jacuzzi tub in the room. Then maybe a tour of some of her new toys, which seemed to get Tammy, really fired up.

Tammy caressed my hand and asked me if I ever had a blowjob while on the highway. In fact, I had, and I told Tammy about when I lived down in New Orleans; the blowjob in question occurred while crossing the 24-mile Lake Ponchartrain causeway. I was seeing this randy sweetheart from Covington, who really enjoyed two things, dancing and sucking cocks. Any way, I told Tammy how this woman and I had gone dancing at one of the clubs in the French Quarter, and this girl had gotten all lathered up. During the ride home to Covington, she started rubbing on me even before we got to the tollbooth. After I paid the torbalı escort attendant, I wasn’t 30-feet away from the booth when she unzipped my pants and whipped out my dick. I can imagine it smelled pretty sweaty as we had been dancing for couple hours and I needed a shower, but she started bobbing her head up and down, coming up every once in a while to see the mile marker so she’d know how much time she had left. She was good enough that I wouldn’t last 5 minutes if she worked at it, but she just worked me up to the brink, and then eased off, in a repeated cycle until we got to the mile maker indicating we had three miles to the north end of the causeway. At that point she really went to work on my cock and with about ½-mile left to go, I exploded in her mouth. She swallowed as much as she could, and what she couldn’t she licked off her hand after wiping her cheek and chin. For me, I almost lost control of the car during the orgasm.

“Why didn’t you stay with her,” Tammy asked?

“I don’t know why she left, but she picked up and moved back to Texas. At least that’s what her neighbor told me. No forwarding address, nothing, so I had no way to get hold of her,” I replied.

“According to the sign we just passed, it is 27 miles to Tomah. I’ll bet I can suck your cock and keep you from cumming at least that long,” she teased.

“OK, bet. But what’s in it for the winner,” I asked playfully?

“The winner gets to try out all the new toys I brought on the loser tonight at the hotel. How’s that,” she chimed back?

“Ok,” I said, “but be ready to put everything back together down there if I see a State Trooper. I don’t want to spend the night in jail. By the way, how are we defining the winner?”

“I give you a blowjob from here until you cum. If that happens before we pass Tomah, you win; but if you don’t come until after we pass Tomah, then you are mine tonight at the hotel. Deal?”

“Deal,” I said, half way hoping Tammy would win because she obviously had something good cooked up.

Tammy grabbed some tissues out of the box I had in the back seat just in case, then she unbuckled and unzipped my jeans. I scooched up a little so she could slide them down just a bit, yet still be able to make things look normal if we got pulled over by the police. When she took my cock into her mouth it felt incredible. It was all I could do not to just put my head back and enjoy the action, but even with the cruise control on; I couldn’t drive with my eyes closed. Tammy sucked and nibbled and pulled on my cock until I was ready to explode, but knew just when to ease off and bring me back to something close to normal. At first I thought there’s no way I’m gonna last 5-miles, let alone 25-miles, but I should have known better. The woman is in complete control in this situation, and if she wants, she can hold a guy off all day. We got a few toots from truckers passing by, and one trucker drove beside us for about three miles with his wife/girlfriend staring out the window into the Jeep as Tammy worked her magic. We were way past Tomah when Tammy finally let me cum. My cock was gushing and gushing. Tammy just kept swallowing. To me it seemed like a pint, though I know it’s nowhere near that much.

As Tammy put everything back in place and zipped up my pants she whispered, “Well, a deals a deal, I guess your mine tonight.”

“I wouldn’t mind if I was yours every night,” I whispered back.

A few miles down the road a Wisconsin State Trooper came flying up from behind us. He pulled up along side of us for about 30 seconds, looked over at us, and then continued south at a high rate of speed. “I guess he heard the truckers talking on the CB and is looking for a little cock sucker,” Tammy said, “but it was worth the risk, and it was fun too.” “Of course,” she continued, “he didn’t suspect us because you don’t have a little cock. In fact, your cock is just the perfect size for me, you know.” I just smiled.

When we got to the hotel, we checked in and went straight to the room. Tammy headed into the bathroom while I went about hanging up my business attire for tomorrow. I could see Tammy through the glass divider escort torbalı that separated the huge oval tub from the rest of the hotel room. She needed to pee pretty badly, but didn’t want me to stop along the interstate in a rest area because, as she put it, “those places aren’t clean.”

When she came out of the bathroom she walked over to the pullout sofa in the living room area. She motioned to me and said, “Come sit with me and I’ll show you the toys I brought for us. Then we’ll go find something for an early dinner. Afterward we’ll come back here to play.”

She set a medium sized sports bag on the coffee table and opened the zipper. The first item she pulled out was the scented lube; I was already familiar with it. Next she pulled out her strap-on harness with the new dildo in it that she had used on me the other night. Then she pulled out a chrome colored, egg shaped vibrator. It had a short cord and a small control box. Next from her bag of toys was a double dong. It must have been 18 inches long; it was very flexible but also rather thick at either end. I was a little nervous and mentioned it to Tammy. “That’s kind of thick isn’t it? I’m willing to try almost anything if it pleasures you, babe, but I think you’re gonna rip me open with that thing,” I said in a quiet tone.

“I thought it might be a little thick also, so I bought this as well,” she said reaching into the sports bag again. This time she pulled out a butt plug. It had the usual taper of butt plugs I’ve seen on the Internet, and it appeared to be about 5 inches long, and at it widest point almost as thick as the double dong. Finally, she pulled out another harness – all leather – with a pouch in the front for my cock and balls, and a strap that is designed to run up the back in the crack of my ass, sort of like a leather g-string.

“I thought we could go to dinner with our harnesses on,” Tammy continued. “I’ll take the external dildo off mine and wear it with the vaginal dildo and clit tickler attached on the inside. I want you to go with your new butt plug in place. The harness will keep it from slipping out of your ass.”

“You may want to go use the bathroom before we continue,” she said, “with the butt plug in place you may not be able to pass gas, and if you’re full then things may get a mite uncomfortable.” Tammy reached down and pulled off my Rockport’s and said, “Stand up now.” As I did she unhooked my belt and jeans, which she then pushed to the floor. I stepped out of them as she was pushing down my underwear. Gently smacking my ass she told me to “get going,” as she pointed toward the bathroom. With a warm feeling of excitement and a bit of trepidation in my belly over the upcoming events, I headed off to the bathroom.

As I sat on the toilet, I could see Tammy strip off her jeans and panties. She unhooked her girlie dick from her strap-on harness and set it in the sport bag. Then she took the rest of the harness and slipped it on, carefully inserting the inner dildo into her vagina. Then she slipped her jeans back on and buckled them up. As she was moving around the room getting things ready for me, I could see how aroused she was becoming from the combination of the dildo and the clitoral stimulator in her harness. She kept rubbing her pussy through her jeans. “Hey,” I called out, “if I can’t play with myself, then neither can you.” She turned her head towards me and gave me a funny grin, then stuck her tongue out in mock defiance.

I finished up my business, wiped real well, and headed out to the bedroom. Still wearing my shirt and socks, otherwise I was naked. Tammy walked up to me and gave me a big passionate kiss. “Kneel on the bed for me, sweetie,” she said, and I did as I was told. “I brought some KY jelly with me because I thought the heat generated by the scented lube might be too much in the restaurant.” I heard the snap of a rubber glove. “I also brought a surgical glove so I don’t have to mess with my nails before we go to dinner,” she said softly. As I looked back I could see Tammy put some KY on the glove. My ass hole puckered as she slipped a gloved finger in. “The KY’s a little cold isn’t it, I’m sorry,” torbalı escort bayan she said. Then she reached underneath and grabbed my cock. As she started stroking it she said, “I’m going to play with you to get you to relax, but I don’t want you to cum, OK”

“Ooo, OK,” I replied with a shudder.

As I relaxed, Tammy got three fingers sliding in and out of my ass. She then started using the dildo that she disconnected from her strap-on. She was reaming my ass pretty good with it when she stopped playing with my cock. I was having a hard time with this as I wanted to just slip off in an orgasm, but remembering what she asked, I started thinking about things from work to try to get my mind off the excitement I was feeling. Tammy pulled out the dildo and paused for just a second, then there was pressure and a bit of pain, and almost like a popping sound as she slipped the butt plug into my ass. The shock of the sudden entrance past my anal sphincter took me by surprise. “Stay there while I get a washcloth to clean you up,” she said walking toward the bathroom. I could hear her taking the rubber glove off. Then she was back with a warm washcloth wiping all around my ass.

“If it was that much effort to put in, how will we get it out,” I asked.

“At the sex shop the girl told me if we can’t get it to slide out after you relax a bit and get used to it, then just some downward pressure from you, like when your taking a crap, will cause it to pop out.” She answered.

“Ok, then how do we keep it in if I get relaxed during dinner? I mean I don’t want it to show through my jeans and look like I have a load in my pants”

Tammy laughed out loud. “That’s where the harness comes in, silly. The rear strap goes through a clip here,” pushing on the butt plug, “and holds it all in place. Ok, after all that excitement and pressure inside, do you think you need to pee? Cause once I put the harness on you, it’s sort of like a little chastity belt; you won’t be able to just whip it out and go, you’ll have to wait until we get back here. Besides, I’d really like you to wear the harness for a while even after we get back here so you don’t tighten up. I have something special planned with the double dong.”

Figuring I don’t want any more pressure than necessary, I went in to the bathroom as instructed. Surprisingly, I was able to pee quite a bit. When I came back into the bedroom, Tammy had my new harness all ready for me. She put the leather pouch in place, making certain all my genitalia were in their proper place. Once this was done, she had me hold the pouch in place while she first adjusted and buckled the waist strap, and attached the rear strap to the bottom of the pouch and to the rear of the waist strap. With everything in place and secure, I felt once again that my ass must look really sexy, cheeks divided, just like when I wore the underwear with the elastic strip. I glanced over my shoulder into the mirror and sure enough, the ½ inch wide strap, cinched in place, really divided my ass cheeks. I could just make out the end of the butt plug from this angle. I could also see Tammy’s reflection smiling as she admired her handiwork.

“OK, handsome, put your jeans and shoes on and let’s go eat something.” I got dressed and was sitting down to tie my shoes when I winced – something was pinching my balls. Tammy saw this and asked me if everything was OK. I told her what was happening and she helped me unhook my jeans. She put everything back in place and adjusted the straps again. Once dressed, I felt much more secure, and was able to stand, sit and move around without pain. “I do feel full, but I’m not uncomfortable,” I said.

“That’s good, honey,” Tammy murmured, “Umm boy, you ass really looks good in those Carhart jeans; the harness kind of spreads your cheeks apart, and the center seam of your jeans is just riding nice on the strap in the harness. Any of the women who check you out at the restaurant will be wanting you tonight.”

“What restaurant did you have in mind,” I asked as we closed the hotel room door behind us.

“I thought we could go to that Chili’s passed when we got off the interstate. It looked busy. We could get a drink before dinner. See, I want you to stand next to me at the bar while I sit on a barstool. I want to show you off to any of the college girls or single women who might be in the bar,” Tammy giggled. But I had my suspicions that she was dead serious, and I better not screw up her plan.

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