My doorman winked at me when he saw the beauty on my arm. My conceit and excitement covered up the discomfort with Janey having called all the shots up to now. I assured myself that things would certainly be different in my apartment. I imagined having her in my bed with her ankles up by her ears.
Janey never gave ground. She poured us both a Scotch neat by the time I hung her jacket. We talked for hours and there was never quite the right moment to make a move. I noted it was past 2:00 AM when she excused herself to use the facilities and I was determined to close the deal upon her return.
Janey threw me off balance by walking past me and sitting across from me in a leather accent chair. She stared into my eyes and spread her legs slightly as she beckoned me to her with a finger. I approached without thinking and felt awkward as I stood in front of her. She reclined back in the chair as she told me to get down. I sat on the coffee table behind me. She lifted her hips in that magical way women do when they are taking off their panties and I couldn't help but stare between her legs as she told me to kneel. I hesitated and in a sterner voice Janey said, "kneel baby... I want to see if your pretty mouth can do more than talk."
The same discomfort arose but I brooked no protest as she wrapped her feet behind my head and brought me into the prettiest pink petals I had ever seen. She gasped as my tongue swept lightly over her clit and moaned appreciatively as I continued to lick her gently. She would direct me occasionally but mostly allowed me to learn how to please her by following her breathing and moans as I licked her.
She fed my uneasiness by telling me that I had teased her all night and it was about time I thanked her on my knees for the dinner. She was further emboldened by my erection that she would occasionally trace with her foot. As her excitement grew, her language became bolder. She told me to look up at her and I felt like one of the countless women I had done the same to as they fellated me. Nevertheless, I knew once I finished with her I would soon be fucking her and the world would be turned right side up again. I put two fingers in her and sped up my tongue on her clit. She came hard and squeezed her thighs tightly on my head as she did so. I expected her to loosen her grip on my head and began to undo my belt as I planned to fuck her right there on that chair.
Janey had other plans though. She kept her legs wrapped around my head and told me to put my tongue in her and to keep looking up at her. I decided to tolerate a bit more in order to get in her pants. I hated her telling me how much she loved knowing that I swallowed and teased me about drinking her cum. It felt emasculating. As though our roles were reversed. My neck began to ache and I tapped her legs to indicate I was done. She smirked slightly and kept me in place for just long enough more to make a point.
She stood up suddenly and was out my door before I could stand properly on my aching knees. I felt humiliated at how Janey had treated me but found myself constantly checking my phone to see if she texted. With no word from her, I slept fitfully and woke up exhausted. I was completely unproductive at work given my constant replaying of the night before. To my chagrin I had to masturbate three times during the day in order to be able to think at all. Every time I brought myself to I couldn't help but think of myself on my knees following her directions.
I waited for her to reach out to me. After the way Janey treated me I knew I would look pathetic to be the first to reach out. After 24 hours I couldn't wait further and shot her a brief text. I broke down and texted again the next day after not hearing back from her. I felt ridiculous. A few days later she texted me a picture of her beautiful pussy with the message, "beg for it." I felt completely flummoxed and my desire to see her again outweighed my common sense and I replied as she asked. I sent about 5 texts in quick succession begging to fuck and lick her pussy but she didn't reply until the next morning with a, "wrong number... lol."
I felt rage and humiliation and swore I wouldn't respond to her again. However, the next night Janey texted me. She apologized for her prior text explaining I was in her contacts immediately above the intended recipient. I appreciated her words but felt jealous that she appeared to be involved with someone else. As we texted back and forth my anger melted and I told myself I was being quite over-sensitive given that we'd been on a single date.
Janey told me to meet her. She was at a club with friends. I was more excited than I cared to admit to see her, nevertheless I was about to decline to maintain my dignity when she sent me a picture of her wearing a skirt so short that I immediately reversed my decision and said I'd meet her.
I gave the bouncer a couple of Franklins to avoid the velvet rope and a hostess brought me to Janey and her friends in the VIP. I was too old for this scene but had a great time regardless. Janey looked amazing and she showered me with attention. After a few drinks and a couple of shots I was feeling no pain. In spite of the loud music we were able to have a conversation. She plainly told me that she liked me a lot but often found men my age to be less fun -- too inhibited and set in their ways. Janey would occasionally lean in and whisper how sexy my mouth was and how she couldn't wait to use it again. I told her how badly I wanted to fuck her. She smiled. Her words were ambiguous, "then do as you're told."
With those words still hanging in the air, she grabbed my hand and led me up to the back of the club. There was a deserted booth and she pulled me in giggling.
"I've always wanted to do this. Are you game?"
I was sure she wanted to fuck and hurriedly began to undo my belt.
"No baby, not yet... lick my ass."
"Oh God, you're not really going to be boring?"
She shifted her weight in a way that made me feel as though she might leave. I felt on the defensive. I grabbed her arm, pulled her in and said, "No... I mean yes... I will..." I felt like an awkward teen as she smirked at me and pressed her advantage.
"You will? You will what?"
"I'll lick you." I knew what she wanted and didn't want to give it to her but knew it was only a matter of time.
"You'll lick me where?"
She smiled to savor her victory and took off her panties. She grabbed my hair and brought my head down. Simultaneously, she raised her feet to rest on the bench she was sitting on and scooted forward allowing me ample access to her derriere once I was on my knees. I thought back to Chloe, a former lover and the only woman I had ever rimmed before. She had insisted I service her in that manner frequently. I'd never debased myself similarly with anyone else. With Chloe it excited me to do so and I found myself similarly beholden to Janey. It dawned on me that they both shared a boldness I found erotic.
Janey brought me in quickly and I found myself licking her rosebud vigorously. On her direction, I began to insert my tongue in her. It took a great deal of coaxing with my tongue but eventually I was past her sphincter. She gasped as I got deeper and deeper into her asshole. I put a finger on her clit. She came quickly and started laughing from pleasure. I sat next to her and went in to kiss her. She turned away from me and grabbed her panties.