Kinky Bargain

I know it's far from being an original fantasy, but I've always wanted to go out with a girl wearing a skirt with no panties on. Just the thought of a girl not wearing underwear under her skirt is enough to send the blood rushing to my groin area and I've jacked off to it I don't know how many times. The only problem was that I had never been able to find a girl willing to do it for me. I always ended up with girls that were too afraid or too prudish to try it.

When I started dating Ginger, I thought she would be the one who would finally fulfil my fantasy. Ginger is a red head and like most red heads had no problem exploring her kinky side. I was therefore quite surprised when she emphatically said she wouldn't go commando under a skirt. This time though I decided to keep asking hoping her kinkier side would win out and she would agree. For ages I would ask her to go commando any time she was wearing a skirt or dress when we would go out. And each time I would receive the same emphatic no and sometimes an eyeroll.

It was our Friday night date night, and I was at Ginger's to pick her up so we could go out. I watched as she was pulling on a navy-blue dress. The dress looked great on her and went perfectly with her pale skin tone and red hair. As she was standing in front of the mirror finishing her makeup, I walked up behind her and wrapped my arms around her and after shifting her hair back over her shoulder kissed the side of her neck a few times.

"You look gorgeous Babe." I said in her ear.

In the mirror I saw her face go from grinning to looking suspicious. "Oh no here we go again." she said.

"What do you mean?" I asked trying to sound innocent as I let go of her.

She turned to face me and said as she put her hands on her hips, "You're going to try to get me to go along with your little fantasy, aren't you?"

I grinned sheepishly as I said, "Well I don't have to ask now since you've already said it. But that does sound like a great idea.

She rolled her eyes before saying, "Good grief. Are you ever going to let this go?"

"No, because the thought of it just drives me wild." I said. "I can't imagine what state I'd be in if you actually did it."

Her face morphed from looking exasperated to looking deep in thought.

"Come on Babe, it'll be fun." I said. "I'm not asking you to flash guys your pussy or anything. I'm just asking you to go commando." I could see the gears working in her mind, which was further than I had gotten any other time I tried to convince her. It was usually just a firm no.

After a few seconds she gave me a wicked grin before saying, "I'll do it under one condition."

"What?" I said instantly.

Another wicked grin as she said, "If I'm not going to be wearing panties than you have to."

Now it was my turn to think. The idea of wearing her underwear didn't exactly appeal to me, but then again this was the closest I had ever gotten to having my fantasy fulfilled. The thought of finally having my fantasy come true sent a pulse down my cock and my mind was made up.

"Ok I guess that's fair." I said trying not to sound too eager.

She didn't say anything but gave me a cute grin before walking to her lingerie chest and digging through her underwear. She began tossing pairs of panties out onto the floor and seeing those undies sent another pulse through my hardening cock. Finally, she stood up with a triumphant look on her face as she held up the treasure she was looking for.

My eyes widened at what she was holding up for me to see. They were silky white panties with red roses printed on them. Thin pink lace and leg bands added to the girliness as did a red silk rose front and center just under the lacy waistband. I remembered seeing her wearing them once and nearly cumming my pants.

"What are you waiting for Baby?" she asked. "These aren't going to put themselves on you." I quickly stripped my clothes off and she held out the panties for me to step into. I slowly stepped in the panties, and she pulled them up. As she slowly pulled them up my legs she had a sly grin on her face. As she pulled the panties up around my waist my already hardening cock quickly moved to full staff. Luckily the panties had a higher waistband than what she normally wore, so I didn't have a problem poking out, but it was close.

"Wow!" Ginger said. "Looks like someone likes wearing women's panties."

I felt heat rising in my face since I couldn't really deny it. She slowly walked around me getting a good look at my panty covered ass before saying, "These look really cute on you." adding to the awkward feeling I had.

Back in front of me she reached under her dress and pulled off the black thong she had on and tossed it to the side. I tried to get a look at her bare pussy, but she didn't lift the skirt high enough for me to get a look.

She then gave me a curious look before saying, "You know you're only wearing half the set. That won't do."

"What do you mean?" I asked before it hit me. When it did, I was flabbergasted. "No way! I'm not wearing a bra too!"

She bent down and picked up the thong she had just discarded and said airily, "Well I guess I'll put this back on."

She had me right where she wanted me and she knew it. I sighed before saying, "Ok get the bra and let's go."

She let out a small giggle before grinning triumphantly as she pulled the bra out of her lingerie chest. She gestured for me to hold my arms out and slipped the bra over them as I did. She then moved the bra up my arms and over my chest before moving behind me to adjust the straps and clasp it behind me. Even with the straps all the way loose it was a little snug but felt oddly kinky. I stole a sideways glance to the mirror and couldn't help but chuckle at how I looked wearing nothing but women's lingerie.

Ginger gave me a hungry grin before running her hands up my body and over my bra and saying in a sultry voice, "God you look sexy like this." With my cock and balls wrapped in soft stretchy silk and Ginger running her hands up and down my body I was ready to stay in and hop in the sack. This feeling was further aroused when she moved south and ran her hand over my hardon a few times through the panties.

"Oh shit!" I cried as she stroked my hardon sending strong pulses through it.

She let off right away and said, "We'll have to finish this later, we've got to go, and somebody needs to get dressed."

"Oh, come on!" I protested. "You can't get me worked up like this and leave me hanging."

"Wow baby!" she said in a sensual voice. "Be honest baby, is it my panties that have you so hard or the fact that I'm not wearing any?" As she asked that she ran a finger up my shaft base to tip sending another thrill through my cock.

"Oh, come on that's not fair!" I said pleadingly.

Ginger smirked at me as she turned and grabbed my pants and tossed them at me saying, "Get dressed we're running late."

I knew I had lost at that point and wouldn't get anything else, so I slowly pulled my clothes on while she watched with an amused smirk as her lingerie disappeared under my clothes. As I pulled everything on, I made sure nothing would be poking out. Boy would that be embarrassing if I had a slip, and someone saw what I was wearing underneath...

"Ready?" she said as I checked myself out in the mirror.

"Yeah." I said trying not to sound nervous.

She then hooked her arm in mine, and we made our way out the door. As we walked, I felt the silk panties rubbing along my cock and keeping it fully hard. As we got in the car, I thought to myself, "It's going to be a long night."