Story Details

Bra Shopping

uberho on Sex Stories

She was a devoted Christian and wasn’t going to have sex before marriage. She was cute, and blonde and about 5 foot 5. I was an atheist but still a virgin, 6 foot 3 and almost athletic. We had gotten tight when my girlfriend had moved over seas. They were best friends so we both missed her. But as time went by we filled the gap with each other. One day we organised a shopping trip together. She needed to buy a present for one of the boys she babysat. And I was going along to help with choose the toy (I am super mature for 18). We flirted and mucked around while shopping, without aiming for it to go anywhere. Eventually we bought a Ben 10 action figure and dropped it at the car. Then we went to grab a bite to eat.



After we finished eating we were discussing what to do next. She said, “I really need to go bra shopping but I’ll have to do it some other time.” But I managed to convince her that it was ok and I wouldn’t be too bored waiting for her to finish. So we wandered into a department store and browsed through the bras. I was a little embarrassed by the situation but she seemed totally comfortable.



Eventually she found about 6 bras she liked and went off to try them on. I was staring onto space when she tapped me on the shoulder. She said “I’ve found 2 that are really comfortable can I get your opinion on them?”

“Sure,” I said. I was a little surprised by this. Our relationship had been friends only so far and I wasn’t sure where this was going to go but I followed her into the dressing room stall. Once I had closed the door behind me she self consciously took her top off. She was wearing a beige bra which didn’t do a great job of emphasising her boobs. Then she turned her back to me and slipped off her bra.



She had chosen a pink bra to try on for me first. It made her breasts look AMAZING! “So how does it look?” She asked.

“Wow... it looks fantastic” I said. She blushed.

“Thanks,” she said. She turned her back on me again and slipped the bra off. She wasn’t as self conscious this time and didn’t entirely turn away so I got some nice side boob vision. The next bra was a lacy white bra and it looked even better. “How about this one?” She asked.

“Even better than the last one,” I replied. She giggled, and then started taking the bra off without turning away. She almost had the bra off before she realised. She squealed and covered herself up. She said, “Oh god I’m so sorry, that might make things awkward.”

I couldn’t help staring; her boobs had been so beautiful. “Don’t worry about it, I really enjoyed It,” I said. “You have beautiful boobs and don’t need to be shy.” She hesitantly finished slipping the bra off. “So you like them?” she said? I just silently nodded.



We stood there silently for about 2 minutes no one game to make any kind of move. Eventually I took a step forward until we were less than a foot apart. I shifted my gaze to her eyes. Then she said, “Did you want to touch them?” I was pretty shocked, I knew she intended to not have sex till after she was married but I guess she had gotten caught up in the moment. I slowly moved my hands to her breasts and started massaging them. She moaned a little and leant into me. Then we started kissing, me still with my hands on her breasts.



She started taking my shirt off and we separated briefly so she could get it over my head. We started making out again and I had my hands on her thighs working them up under her skirt. She was untying my shorts and I finally reached her underwear. I slipped my thumbs under it and pulled it down. By this stage she had my shorts untied and pulled down about 6 inches. She stepped out of her underwear and left it on the floor. She pulled my dick out of my pants. By this stage it was quite hard.



I lifted her up and she straddled my hips. Her now damp pussy was rubbing on my dick. She started moving back and forth rubbing my shaft along the outside of her pussy. She was moaning gently as she did. I was now rock hard as I lifted her up a little higher so that the tip of my penis was pushing gently at the entrance to her vagina. I knew she was a virgin and also rather small so I knew this was going to hurt her so I left her in control. She gently lowered herself down. It was too tight. My dick wasn’t fitting in at all. It felt incredible from my end but she was now biting my shoulder rather hard so I imagine it was hurting her quite a bit. She slowly inched herself down my dick. Finally there was a sensation of release and she slipped all the way to the base of my shaft. She bit down extra hard and then released.



Now she slowly started moving slowly up and down my cock moaning gently as she did. I was in ecstasy, she was so tight. Once she seemed to be in no more pain I pushed her against the wall and started thrusting hard into her. Her moaning got louder, by this time we had totally forgotten where we were. Finally, just as I was beginning to feel I could hold on no longer her pussy began to contract as she orgasmed. This set me off and I ejaculated deep inside her.



After we finished we cleaned up and left the stall. She bought both the bras and we headed to her house. We had sex one more time then I left her to it. We never had sex again and our relationship was very different because I had been involved in destroying everything she had lived for.

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