My second submission (ha, ha) with Meg. Love hearing comments, especially from any women who have tried this (or want to!)
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The morning after Meg took my anal virginity was surprisingly normal. She woke up and made coffee while I stumbled to the shower, and then we both hung around on the balcony like any other Sunday morning. Neither of us talked about what had happened the previous night. Not because it was taboo, I don't think, but because Meg was giving me time to process.
And I probably did need a little time to process. She had violated me so completely- turned the tables so completely- that there was still a part of me asking whether it was OK. But it was, I realized. Nothing changed. We were just two adults having fun, and if it was a turn-on for her... well, it was a turn-on for me too.
I couldn't look at her quite the same way when I passed her in the hallways at school, though. Her pretty green eyes would flash at me, and I thought (or was I imagining?) that there was a mischievous hint of teasing in her glance. Like she was saying, "We both know what I did to you..." But she never said anything, it was just the look... just once, when we were in an elevator together, she slid her hand up the back of my ass and squeezed lightly. I would have said something, but there was a senior secretary in the elevator with us. Who would have guessed that this 32-year-old TA would be so devious?
We had sex a couple of times in the month after that, and she put her finger in my ass while going down on me, but we never repeated the full-on exploration of that first night. I was relieved, and also a little disappointed. I started thinking about it when I was alone, when I was masturbating, and then even when I was inside her. I decided that I wanted her to take me again. I just needed to get up the courage to ask.
Her birthday had passed, but mine was coming up, so that seemed like the perfect excuse. I playfully texted her and asked her what I should expect for a present.
"Oh, I have something in mind. Something I KNOW you want..." she texted back.
"Hmm... How do you know I want it?" I asked, trying to be clever.
"Because EVERY guy wants it," she replied, with an evil smiley face.
Well shit. I guess I didn't have to guess what that meant. I nervously (and excitedly) looked forward to my birthday weekend.
Friday night finally arrived and I had prepared for the event. My bedroom was well-stocked and I had even taken the liberty of inserting a medium-sized plug to loosen up my ass. She told me that she would be coming over about six, and to be "ready." So I was.
At 6:15 she knocked on the door and I answered. She looked fantastic- in fact, she was all dolled up, with a glittery black cocktail dress and heels. She wore silver hoop earrings and had put on makeup. I must have looked a little surprised, standing there in jeans and a T-shirt.
"Come on, hurry up and change!" she said.
"Change? Are we going out?" I stammered.
"Yes, of course. You didn't think we were going to spend your birthday holed up in your apartment, did you?"
Well, YES, actually. But OK. I ran back inside and looked around my closet, realizing that I would need to take out the plug also. How was I going to non-awkwardly do that?
"Here!" she said, grabbing a red collared shirt off a hanger. "Just wear this. Jeans are fine, just put on nicer shoes."
"Ummm.. no, I can wear something else, I just need a minute..."
"Taxi's waiting! Come on!"
Taxi? How was I going to get out of this one? Shit. There was no option really- Meg could be insistent when she wanted to be. I grabbed the shirt and followed her down the stairs and into the back of the cab. As I sat down, I could feel the plug pushing deeper. My cock surged.
I must have let out a sound, because Megan leaned into me and whispered, "Everything all right?"
I nodded nervously. "Mmmhmm."
She grinned. "Good. You have a big night ahead of you!"
We arrived at a trendy wine bar-club and walked to a circular booth in the corner that Meg had evidently reserved. The lights were turned down low and the decor was warm, but there was lots of energy in the air as people mingled about on a Friday night. I had a couple glasses of wine and felt more relaxed. The plug had settled in comfortably and was even turning me on now... since the lights were low I wasn't so worried about anyone seeing my raging hard-on.
Halfway into our second glasses, Meg excused herself to go to the bathroom and I sat surveying the crowd. I'm a man like any other... I couldn't help looking, and besides it was my birthday! At the corner of one end of the bar, I spotted a pixyish girl in a shiny green dress and my gaze paused. She was younger, probably mid-20s, and had light brown hair cropped close to the shoulder. She was thin, with probably B-cup breasts, but she was really cute. Although not the "model" type, she looked like she would be a lot of fun in bed.
Unexpectedly she turned toward me, and our eyes met. She smiled, turned back to keep talking, but then she looked up at me again. I realized I was stupidly staring at her and looked away, turning back to my half-glass of Pinot Noir. Blushing, I glanced up again and saw she was walking toward me.
"You seem to be taking up this whole table yourself. Kinda selfish, don't you think? It's Friday night." She put her wine glass down on our table and scooted in next to me.
