I've never been a fan of online dating, but I keep myself open to the romantic possibility nonetheless, hoping that someday I might find someone special. Without much active searching, a brilliant seductress found her way into my online world. Despite my effort to not grow an attachment to her, she skillfully pulled me into her web. I was miserable storing such strong feelings behind a screen.
She toyed with my feelings and insecurities relentlessly, and I was already in the process of convincing myself that she wasn't worth the heartache. She was worth the heartache, I just didn't have any input in the pace of the relationship or if or when she would give me attention. The buildup over a matter of months was quite painful, to say the least. I couldn't believe that she finally offered me a date.
We both took trains into the city and agreed to meet at the station. She dressed casually and elegantly, tight black jeans with a long black coat, and red lips. I wore my favorite jeans and converse sneakers. I told her that she could identify me by my multicolored knit hat with the homemade pom-pom. She found that amusing and did not hesitate to mock me for this fashion choice. Finally, we stood face to face, and I felt like I had known her for such a long time.
Early in our date, she asked me about my underwear preferences. I told her that I wear men's boxer briefs often, but most are different brands from over the years, a trophy collection of sorts. She asked what kind I like to buy for myself, and I answered that I like the Calvin Klein style that are really tight with a huge dick pouch. I joked that I like my ass to look cute and my dick to look huge. She did not laugh. She simply looked me up and down and told me that she was going to incinerate my dick. Her straight face made me want to retract my joke, but she had already moved past it.
She told me that she wanted to take me to Nordstom's to buy a new favorite pair of boxer briefs. She wanted to own the first pair that she was going to make me soak through. I swallowed hard as she hailed a cab, trying to hide the fact that I was already soaked through my current pair.
We made it to the department store and went to the men's underwear section. I picked out a pair that was exactly my style, and she nodded and told me that they suit me. She suggested that I go try them on, just in case. I walked into the small dressing room, and she was right behind me. As soon as I passed the threshold, she quickly pulled the curtain shut.
She kept her eyes fixed on me as I removed my pants and already damp panties. She thought it was cute that I was wearing lace panties for our date and laughed at me for even pretending to be a lady. I picked up the new pair, and I was about to try them on.
Before I even started trying them on, she grabbed me by the throat and threw me against the wall. Her fingers wandered to my dripping cunt, and she was pleased to find me already soaked. She slipped her fingers inside me, pressed her palm on my clit, and she tightened her grip on my throat. I could barely breathe, and she told me that she wanted me to give her a good strong orgasm right there in the fitting room.
She loosened her grip on my throat so I could get some air, and I started moaning. Her fingers were driving me wild. My moans grew louder, and we heard the fitting room attendant and saw her clunky work shoes halt outside our dressing room. The kind clerk asked if everything was ok, and my date roughly covered my mouth and responded for the both of us. She thanked her politely and said that we were doing just fine.
Once the attendant passed, my date kept her hand over my mouth. She reminded me to shut up and behave myself. She pushed deeper and told me to give her my cum and stay quiet. I squeezed her fingers so tight, and her hand muffled my whimpers. When she felt me shaking, she whispered that I was being such a good girl. She told me that she wanted me to cum, and I came for her on command.
She took her hand off my mouth and licked her fingers. After tasting me she smiled and said, "Oh sweet girl, looks like you don't need new underwear to soil yourself for me after all." Then she picked up my new favorite boxers and exited the dressing room. She told me to pull myself together and she would be waiting at the register.
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