A Little Shy

by JAX

Copyright© 2003 by JAX

Sex Story: I'm a little shy and my boyfriend's sister had to help me dress more sexy for a party

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   NonConsensual   Drunk/Drugged   Lesbian   Heterosexual   First   Sex Toys   .

I've always been a little shy so when Toby asked me out on a date, I didn't say yes straight away. The more I thought about it the more I knew I wanted to go out with him. Although sweet he was very assertive with me. On the way home from the pub he stopped the car in a dark lay-by and he started to kiss and fondle me. At first it was very pleasant feeling his hand on my breasts, but I knew I should stop him. After a little struggle he re-started the car again and took me home. I lay in my virgin bed, my breasts still tingling from his touch, it had felt so nice, but I knew I should have stopped him. The next time he took me out it was the same. But this time he managed to undo my blouse buttons to allow his hand inside and on to my bra. It funny, I wasn't thinking about what he was doing to me but how I wished I had worn a more sexy bra, not that I owned any of course. By our fifth date I had become used to his hands on my body, I would fight him for awhile but eventually I would allow him access.

He told me one night, just as he dropped me off at home that on Saturday we had been invited to a party. He picked me up at eight and we drove off. I could see he wasn't happy, I had worn my best party dress but somehow he didn't like it. We drove to his sister's house where her husband Bill answered the door; his sister Kathy took me up to her bedroom.

"Now let's see if we can find something for you love shall we," she said, "you and me are about the same size."

"T-thanks," I stuttered feeling very uncomfortable.

"Take that dress off love while I find something," she said and she started to rummage through her wardrobe. "Yes this should do, now come on love if you don't get a move on the party will be over before you get there."

I unzipped my dress and it fell around my ankles.

"God girl who bought those undies, your Auntie," she said, I hung my head in shame. "Good thing you can't wear a bra with this dress anyway," she said brightly, "so whip it off and put this on."

With my head still down I unclipped my bra and that too fell to the floor.

"God girl," she exclaimed, "you shouldn't be covering those beauties up, nicest pair of tits I've seen I a long time."

As quickly as possible I pulled the borrowed dress over my head and I smoothed it down. There wasn't much of it, the barely cover my knickers at one end and the two thin shoulder straps just kept my breasts covered.

"Please I can't wear this," I complained.

"You look great, now off you go and have a great time," she pushed me out of the room and downstairs. "Now little brother you have a good time and promise to bring Angie her over one night ok."

"Ok sis," he agreed and off we went.

On the drive over I kept trying to pull my short skirt down a little more but it was just too short. Despite my borrowed dress I had a good time, mostly in Toby's arms dancing and on the way home my lack of dress help him to get his hands onto my naked body. Before too long it was bunched up around my waist leaving the rest of me exposed. I couldn't help it, his hand found their way under my knickers and soon my legs just opened up for him. On the drive home I wondered if I was still a virgin, his fingers had entered me and had made me have an orgasm, did that count?

A couple of days later he told me to wear his sister's dress again, plus to put a few things in a bag to change into as we were going to her house for a drink. I felt very exposed sitting on her couch, the short skirt exposing my thighs to every one gaze, I especially noticed her husband looking at my legs. After a few drinks his sister Kathy grabbed my arm and pulled me up stairs.

"Let get you to try a few more of my outfits," she giggled, I think she was slightly drunk, I think I was too. Before I could stop her she had unzipped me and my dress was off.

"Did I tell you you've got great tits," she said.

"Yes," I replied, feeling a little embarrassed.

"Here you put this on," she said handing me a dress, "while I put this on."

Once my new dress had cleared my head and I could see again, I saw she was now almost naked herself; she was only wearing the smallest pair of knickers I have ever seen. I couldn't help but look, her breasts were smaller than mine but they stood out straight from her chest.

"Let's go and show the guys," she said and pulled me from the room.

"You two look stunning," said her husband.

"Yeah great," agreed Toby.

"Put some music on and lets have a dance," said Kate.

Toby came into my arms and he kissed me, the room lights were dimmed and soft music filled the room. I was very aware of how little I was wearing. After a few records Toby left me to dance with his sister while her husband took me into his arms. His hands were all over me, I couldn't say too much so I just kept moving them off my backside. I was happy to have Toby back in my arms again. Eventually I got home only to discover I was still wearing her dress.

"Come over later," Kathy said on the phone, "Bill's away until late on business."

She picked me from my front door and she drove back to her place. We sat and chatted over a bottle of wine.

"I've brought your dress back," I said holding up a small bag.

"Good, I've got lots for you to try on, grab that bottle and let's go," she said.

Again in her room she started to pull dress after dress from her wardrobe.

"Here try this one," she said holding up a two piece in white. I unzipped my dress and reached for the outfit.

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