I didn't realize how tired I really was until the alarm went off at 9:00 a.m. on Tuesday morning. Having gone to bed the night before at 11:00, I had slept ten straight hours without interruption. Given the activity of the last few nights, I certainly needed the rest. I put myself together and made it to the DelTex office by 10:00, finding all the necessary parts had arrived to allow me to continue my work. After a very long but productive day at the office, I found myself back in my hotel room at 8:00 and ordered some room service so that I could shower and relax in the room and have a quiet meal before heading to Helen's room and getting my reward for last night's services to her clients. Just after finishing my meal before 9:00, I got a phone call from Leah and worked her through another phone sex orgasm. She wanted to go on and on, talking about how much she missed my tongue and dick, but I finally got her off the phone just before 9:30. I didn't mention to her mom was in the same hotel and that I was heading down to her room to fuck her in the ass.
I threw on a pair of slacks and a shirt (no need for boxers) and dabbed on some cologne before making my way back to Room 423. Upon knocking, the door opened and I saw Helen standing there in a very skimpy robe being held in place by a sash-like belt. She embraced me for a kiss, then turned to walk over to her make-shift bar on the dresser and handed me a drink. We made small talk for a couple minutes as we sipped our vodka drinks, but Helen apparently couldn't wait any longer and reached to unsnap my pants. She seemed a bit surprised when my pants fell to the floor and my cock sprang out, free of any boxers. She immediately wrapped her hands around it as we both leaned in for a deep French kiss. My hands reached down under her robe to her bare ass and I discovered that she too had passed on any undergarments. I squeezed her fleshy ass cheeks in excited anticipation of where my cock would be sliding shortly.
I was standing in front of the bed at that point and sat down, putting my finished drink on the nightstand before reaching to undo the sash holding Helen's robe together. I pulled her to me for another kiss as the robe pulled away, and then guided her to her knees so that she was staring my cock in the face. She took the hint and enveloped my dick with her mouth, allowing the head to scrape her throat as she deep-throated me. I pulled off my shirt as she continued, pulling back and attacking the head of my cock with her tongue while she gently tugged my balls with her hand. I grabbed the back of her head and pushed back and forth a few times to let her know I wanted her to fuck me with her mouth for a while at a slow steady pace before reaching down to massage her ripe melons. After a few minutes I pulled her from me to keep from cumming in her mouth. We switched places, and I went down on her juicy twat, which was nearly dripping at this point. It did not take long for my tongue action to get Helen off and she moaned in delight as her legs did their best lobster imitation to clamp my head to her pussy.
She finally relaxed and I was able to turn her on her side so that I could kiss her asshole. She squirmed and gasped as I licked her brown bud. She had obviously taken a shower just before my arrival as she was very fresh down. I moved my tongue to gently nibble her ass cheeks as I moved a finger up to prod her hole and loosen it for my cock. I wetted my finger with some of her pussy juice and then buried the first two knuckles inside her butt. I added a second finger and rotated them slowly as reached to pinch her nipples with my free hand. Sensing she was ready, I told her to get on her hands and knees. She complied as I stood behind her, my cock bobbing with anticipation. When I started rubbing the head against her ass instead of her pussy lips, she flinched and said,
"What are you doing? Are you gonna stick that in my ass? I've never done that. It's too gross. Please just fuck my pussy?"
Another anal virgin!! Like mother, like daughter, I guess. I reveled in the thought of popping first daughter and then mother's anal cherry. "Now, now," I replied. "I think last night you said I could do whatever I wanted with you tonight. Trust me, you will love. Just relax."
She flinched and tightened her ass cheeks as I started to push in. "Please, please, no," she pleaded. "I'll do anything else. You're too big for that."
"You saw me with Sheila last night and she was smaller than you. Let me just put in a little to see how you like it. Reach down to rub your clit to distract yourself. And relax, it is much better if you relax."
She softened her clench on her ass a little as her hand reached down to toy with her clit. I slowly wedged my cock into my third virgin anal hole in less than two weeks, having first taken Leah's, and then later her roommate, Kelly's. Helen whimpered as I invaded her ass one inch at a time. When I had gone about three inches, I stopped to let her adjust. Her ass was so tight, I knew that she was telling the truth about this being her first time. I grinned to myself in delight as I began slowly thrusting myself in and out, going a little deeper with each thrust. She could not hold herself up in front with one hand any longer and slumped down to her shoulders while still on her knees. This position allowed her ass to stick straight out for my pleasure as she continued diddling herself. She seemed to be relaxing and getting more into it as I finally felt my balls slap against her pussy, signaling that I had hit bottom. She began a low guttural moan as I starting plowing her virgin ass with faster strokes.
"UUUUUUUUuuhhhhhhhhhh. Oh fuck. I'm cumming. I'm cumming with a cock in my ass." Helen trembled against me in an explosive orgasm, spurring me on. I was much too close myself to relax and let her get a breather as she recovered so I continued on, increasing the pace of my thrusts. I was pounding her with all I had and knew that I would explode at any second. While the thought of cumming deep in her ass was appealing, I had a better idea and withdrew from her ass, grabbing her right hip and turning her on her back. I climbed up between her and sprayed my load over her tits and face, splashing her on her left tit, chin, mouth, nose and forehead. I grabbed her tits together to rub my cock between them before moving up to offer my softening dick to her mouth, rubbing it against her lips. She didn't hesitate to open up and swirl her tongue around the head, licking it clean. I guess the fact that it had just been up her virgin ass either didn't register with her or didn't bother her as she sucked off my remaining semen and the remnants of her ass scum.
I finally released from her and lay back. As we rested, I stroked her hair and said, "See, that wasn't so bad was it. You seemed to enjoy it once we got going."
"I never knew it could be so good," she responded. "Here, I've been limiting myself all this time. I should have tried that sooner. Where have you been all my life."