Ginny and Jake

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"I though you took those off?" she said.

"I wanted to surprise you, I thought you liked seeing me wearing them."

"I did, I mean I do, I mean," now it was her turn to stammer.

I put on my swim trunk and got out of there.

When Ginny came out, she was wearing a pink bikini. Where she managed to hide her cock I don't know, but I couldn't see any bulges.

"I'll show you later," she guessed at my unasked question. "Do you like?"

"You look very sexy" I told her.

She sat down and we had a leisurely lunch followed by some pooling, and just a little fooling, I was having a hard time keeping my hands off of her, and she didn't resist much.

While we were drying off, Ginny asked, "Was there anything you didn't like about wearing my panties today?"

"You don't give up do you?" I kidded her. "Ya want the truth?" "Wearing your panties today gave me a hardon. Everytime I moved I felt the silky material rubbing on my cock. I damn near had an orgasm sitting at that café waiting for you. That's why I let my shirt hang out, to cover up a little. But, to answer your question, the material did snag a little on my hair, is that what you wanted to hear?"

"Then you'll just have to shave," Ginny cryptically.

Ginny took my hand, (I was getting used to that) and led me back into the house. In the bedroom, she reached up to kiss me and I pushed her last words into the back of my mind and forgot about them.

Ginny's kisses made me forget most everything as we cuddled in bed. Ginny pushed my head down towards her cock and I didn't hesitate in sucking her already erect penis into my mouth. After a moment or two, she pulled away and turned around on the bed. My mouth found her cock again and I felt my dick being drawn into her mouth. We brought each other to an almost simultaneous orgasm. We stayed in that position for some time. While I was playing with Ginny's tight ball sack, I felt one of Ginny's fingers exploring my ass hole. Ginny was able to reach a tube of lubricant and slowly massaged some into my hole. She started to probe with her finger and I felt it slip in. I was a bit apprehensive, but there was no discomfort or pain. I relaxed and concentrated in Ginny's balls. When she put two fingers in my hole, I felt pretty full. It didn't feel bad, just different. We eventually had to get up. We took a shower together and took turns washing each other. And of course there was more kissing.

While we were getting ready for dinner, without thinking, I mentioned that this was starting to feel like a honeymoon. As soon as those words got out, I regretted saying them. That just couldn't happen, for a lot of reasons.

Ginny looked at me and said "I know, I know, but if things ever changed, I would say yes."

I shut up.

Ginny had a surprise waiting. She had arranged for someone from her catering staff to have dinner ready for us. We were seated at a small table just off the kitchen and served a wonderful meal.

Ginny asked, "Would do something for me?"

"Ginny, I'll do just about anything I can for you if I can, what's up?" I said.

"Something I think will be fun, something I want you to try, something I think you'll like." She pressed.

"Ginny, I told you I will do what you want, now what is it?" I asked.

Just at that moment dinner was brought in. Ginny lit the table candles and the waiter from her staff opened a bottle of wine. We started with a small salad and worked our way through broiled salmon, riced potatoes and more wine. I settled back with a fresh cup of coffee and thought about the last few days.

After dinner we sat in the garden, looking at the stars. When we got back to the bedroom later that evening, I saw that she had laid out some of the packages she had bought earlier. She started unwrapping and showed me several items of new lingerie. Every item was black and very lacy.

"Very sexy I told her, you're gonna look great." I said.

"These aren't for me," she said. "Remember, your promise."

"You got these things for me?" I asked.

"Wearing your panties today was one thing, but, but, but," and yes, I was stammering again.

Ginny showed me three pair of panties, two different bras, a garterbelt, several pair of stockings, and a short slip.

"I had to guess at your size, but these should fit." She offered.

"Is this why you said I would have to shave?'

I sat down and stared at Ginny.

"Well, you said that you did enjoyed dressing up before. I'm guessing that it gave you a thrill. And you said that wearing my panties today felt good, and it brought back some pleasant memories. . I think you mentioned getting a hardon," she kidded.

She had me there. I did say that. And it really did feel kind of exciting wearing her panties all day. Our admittedly rather bizarre relationship was getting even more bizarre by the minute. But, what the hell I thought. My cock was getting stiff thinking about it.

"With a smirk, I said," I don't know anything about shaving, except my face." "I'll do this on one condition, you have to do the shaving."

"Ginny brightened up and said, "Deal"

We were busy for the next hour at least. Ginny lathered and shaved my legs, my butt, and around my cock and balls. She shaved my face and neck and massaged moisturizer everywhere.

She showed me how to put on the garterbelt and how to roll the stocking up my legs. I will admit that the stockings gave me a whole new sensation, and I confessed to Ginny that I liked it. We tried on one of the bras and it fit perfectly. When I pulled a pair of the panties, on, there were no snags. These fit better, being a larger size. When we were done Ginny stepped back and whistled.

"You look better all dressed up than I do," she said.

I looked in the mirror and saw myself like I never had before.

"How do you feel?" Ginny asked.

She didn't ask how the lingerie felt. She asked how I felt.

I felt different. I told her that. And I told her that I had never been that turned on before.

"Well, you look fantastic." Ginny said. But something is missing.

"You've gone this far, would you go just a little farther?" she asked.

Now I'm standing in front of a mirror, all dressed up in black lacy lingerie and my cock is straining the front of the panties. What else could I say.

Ginny brought out several more packages. Ladies shoes with low heels, a dark blue skirt and a medium blue sheer blouse with a matching vest. When she was done 'dressing' me, I felt silly standing there. But I also felt strangely excited.

Ginny took my hand and we walked out on the patio. This is more that weird I thought. I was starting to get nervous, and Ginny could see that she might have pushed this a little to far. Once back in the house Ginny asked me what was wrong.

"Ginny, earlier tonight this was fun, a bit crazy, but fun," I told her. "But."

"Don't be mad, I just thought," she started to say. I stopped her with a kiss.

"It's not you, it's me." When I was younger, like I told you, I tried on some of Mary's things. Thinking back, I think I secretly wanted her to catch me, but she never did. I remember thinking about going out and having a stranger catch me.

I don't know what I was looking for. Tonight kinda brought it all back. "

Ginny was quiet. We got undressed and I put my new lingerie away. Did I just say 'my' lingerie? That night we snuggled but we didn't have sex.

After breakfast the next morning we made plans to spend the day out. We went miniature golfing and stopped for ice cream. We found our way back to the Galleria and walked though the mall. I bought Ginny some flowers. Ginny parked me at the same café again and did some shopping on her own. I had a coffee and happily watched the world go by. When Ginny returned with more packages, she ordered a cup of coffee too and we talked.

"I'm sorry about last night," she said. I don't want to change you. I like you just the way you are. I don't want to take a chance that you might decide to walk away."

She took a deep breath and I could see she was ready to cry.

"Ginny, I am not going to walk away. Our relationship, although very odd, is important to me. I never in my life thought that I would be involved with someone like you. But I am involved. It's too late for me to walk away. I'm afraid that I care too much about you now." "Besides, it would be a shame to throw away all that sexy lingerie."

Ginny smiled, then she laughed, and then I laughed. Then the waiter brought us fresh coffee and we realized where we were. We laughed again and did some more window-shopping.

The rest of the afternoon flew by. We acted like kids. Back at the house we sat in the hot tub and played in the pool. I got Ginny into a corner where the warm water was about up to our waists. I slipped off her bikini top and my mouth caressed her firm young breasts. I sucked greedily on her nipples. In the sunlight her areolas were sparkling with pool water and the tender skin of her breasts yielded to my questing mouth. Ginny slipped off her bikini bottom and grabbed at my swim trunks. I kicked them off and I felt our cocks rubbing on each other. I grabbed her ass with my hands and lifted it towards me. The warm water provided enough moisture for my cock to enter her tight hole. We both squirmed around until I had my entire length buried deep inside her. As I stated moving in and out, the pool water

increased the suction of my thrusts. Ginny wrapped her arms around my neck and our tongues imitated what was happening lower down. Ginny reached her orgasm first, but not by much. She gritted her teeth and let out a long deep moan of pleasure as I emptied my load. I reached down to her cock and gently washed away cum that she had squirted.

We splashed around a while longer, and then went in for a shower and an nap. And while I was waiting to fall asleep, Ginny curled in arms, I did some thinking, some soul searching and a lot of remembering.

We woke up about dinnertime.

I asked Ginny, "What do you want to do with the rest of the evening?"

"I don't know, got any ideas." She answered.

"Well, I was thinking, James and Mary should be back tomorrow or the next day. If we wanted to do anything special, tonight might be our only chance for a while," I told her.

"I thought that we might go out, find a quiet little place, and have a drink or two," I offered.

"Sounds ok to me," Ginny said. "Let's get dressed."

I sat on the bed for a minute and then started getting out the new lingerie that Ginny had purchased.

"What are you doing?" Ginny asked.

"Getting ready to go out," I said I looked at her and smiled.

"You're not serious?" Ginny said.

"I thought if you're willing to help me if I start to panic, I'd give it a try. I think you were hoping I would anyway."

Ginny looked at me with a funny little smile, and said, "I think I have everything you'll need."

I've seen that look once or twice before.

"And just what have you got planned young lady?" I inquired, with a grin

"You're really serious?" She asked again "

I could have said no. I could have said that this was crazy, and to forget about it. I could have said a lot of things.

What I did say was "Ya, I guess I'm serious."

For a minute, it sounded as though the whole world got quiet, waiting to hear what she was going to say.

"You mean it, You'll go?" She said.

"I said I would, now help me get ready before I change my mind," I told her.

Ginny said, "I know a small bar that isn't usually too busy. It's dark inside. We could sit in a booth, have a drink or two and leave."

All of a sudden Ginny stopped. "Wait a minute" she stammered. Ya, she was stammering too.

"What do you mean that you care too much to walk away?" She demanded.

She looked up at me with those beautiful green eyes. She had her hands on her hips and her head tilted to one side.

"It took you long enough," I told her.

I took a long deep breath. "Ginny, I am a married man, at least in spirit anyway, and I'm a lot older than you are. And, to be honest, I'm not sure how things will work out in the future. I can't offer you any kind of normal life, but I think I might be falling in love with you."

Ginny stammered again. See. I'm not the only one that stammers.

We steed there, staring at one another. Ginny had her mouth open, but no sounds were coming out. Finally she spoke.

"Then there is only one thing to do," she said.

"Let's get dressed." We both said at the same time.

Ginny helped me with the garterbelt and stockings again, and I put on the panties and bra while she was getting herself dressed. I stepped into the short slip and then the dress, settling them around my waist. I put on the blouse but before I could button it, Ginny opened a small box took out what was inside.

"These are the ones I used to wear before I got these," and she cupped her own beautiful breasts.

She slipped the breast forms that were in the box inside the cups of my bra and suddenly I had curves. Did I just say My Bra? She helped me button up because the buttons where on the wrong side and my fingers weren't working like they usually do. I put on the little matching vest, and slipped my stockinged feet into my shoes.

When she turned me around to look in the mirror, I couldn't believe what I was seeing. Another woman was looking back at me. Well, almost. Ginny pulled out one of her brunette wigs and got it settled in place.

Almost ready she said, and took out her makeup bag. I was involved much too far now to object. She applied a soft pink lipstick, put a little blush on my cheeks, and handed me a pair of amber sunglasses.

"Sunglasses are easier than trying to do your eyes, and we will only be there for an hour or so anyway," she said.

I wasn't nervous at all as we got to the bar about nine thirty that night. The hell I wasn't. I was shaking. This was nuts. I'm not a crossdresser. I had to stop this.

Ginny told me to take a deep breath and led me inside. Luckily there were only a few other people in the bar. We found a booth in a dark corner and ordered a couple of drinks.

When the waitress brought our drinks, she evidently recognized Ginny.

"Hey girl" she said, "been a while."

"Who's your friend?" she asked, "TG or CD?"

"CD, a newbie", Ginny told her. "First time out."

"I'll keep an eye open sweetie," the waitress said and winked at Ginny.

Ginny looked at me and said, "I'll explain later, but Rhonda will run interference for us, she helped me a lot when I was coming out and going through hormone therapy."

Over the next hour or so, several more customers filtered in and someone started playing soft music on the radio. A few looked our way, but after a word from Rhonda, they left us alone. We had another drink and talked. Slowly my nerves quieted down. About eleven o'clock we left. Ginny stopped at the bar and gave Rhonda a nice tip.

"I can't believe I just did that." I said, as we left.

"Did you really have a good time?" Ginny asked.

"The only thing that could have made it better would have been if some guy had tried to pick me up." I told her.

Once back in the car, Ginny moved it to a dark corner of the little parking lot and turned the motor off. She moved closer to me and slid her hand under my skirt. Did I just say My Skirt? Her hand-felt electric as it moved up my nylon covered thigh. I moved my legs as far apart as my skirt would permit. I finally lifted my butt off the seat so I could hike the skirt and slip up a little higher. Ginny started rubbing my straining cock through the thin fabric of my panties. And.

All at once, the bar's night crowd arrived. The parking lot was suddenly full of headlights and people.

Ginny asked, "wanna go back in, maybe someone will ask you do dance?"

"I think I've been brave enough for one night." I replied.

We drove around for a while and by the time we got back to the house it was after one in the morning.

Before we got out of the car, Ginny managed to get her hand under my skirt again. I moved her hand long enough to unzip my skirt and take it and my slip off. This time Ginny had no trouble moving up my leg and finding my rock hard cock. I leaned back in the seat as she inched my panties down far enough to get my cock free. It was only a second before I felt her hot mouth envelope my aching cock. She found my balls, still covered by the lacy nylon panties and massaged them while she sucked me deep into her mouth. I warned her that I was going to cum, and she clamped her lips tightly around my cockhead and sucked up every drop as I pumped my load of hot cum down her throat.

Once we were back in the bedroom, Ginny asked if I had a good time.

"At the bar or in the car?" I kidded her.

"You know what I mean," and she poked my in the arm.

"I had a great time." I told her. "Maybe next time you could get a date and we could double" I teased.

"Why you," was all she managed to say before I grabbed her and covered her face with kisses.

We did manage to get undressed and just before Ginny fell asleep in my arms, she whispered "I love you Jake."

In the morning, we woke up earlier than I thought we would. Without getting dressed, we stopped in the kitchen long enough to make coffee, and walked out to the HotTub. We relaxed in the hot bubbly water and sipped our coffee.

"Got any plans?" I asked

"In our goofy relationship with James and Mary, I don't know what plans I could make." She answered.

I agreed with her. What could we plan?

"We have today and tonight, what do you want to do?" I asked her.

She took my hand, and we jumped into the pool, like love struck teenagers. After all, it was sort of like a honeymoon. The reader can guess what we did for the rest of the day.

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OOAAOOAAabout 2 years ago

SUPER HOT!!!!!!

sirhugssirhugsalmost 14 years ago
very hot story

but the poor use of quotation marks and occasional grammar errors are distracting.

Hope to read more of Jake's descent into debauchery.

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