Kathy did live nearby, but we had to get back to work because she still had work to do, though she could finish it past the end of the normal business day, so we didn’t have a lot of time. Her apartment was a small single. She was obviously not making a lot of money—or she was saving a lot living there. I didn’t ask.
Now, I am not a guy hung up on virginity, but it did cross my mind that this was the situation I was in. Attractive or not, I didn’t want to blow this chance. I decided just to take control of the situation. “So you’ve really never had sex—Are you nervous?” Yes and yes. “Let’s not rush. I want you to be comfortable.” The apartment only had a bed, a chair, and a table with a small television facing the bed. She was still holding her purse; she carries it everywhere. I directed her to put it down, and she set it down on a counter in the alcove kitchen.
“Come here,” I directed, and I caressed her shoulders and tried to make her feel welcome. Though I wasn’t really into it, I ran my fingers through her medium-length hair and rubbed her scalp with my fingertips. Then, cupping the back of her head, I pulled her toward me and kissed her firmly—and I held her there as I tried to relax her—to at least, as I said, make her feel welcome. Though it wasn’t great—and she did return the kiss—, I told her she was a natural, that I couldn’t believe she hadn’t done that before. And I gave her some more. She was either getting a bit more relaxed, or I was kidding myself. Either way, perception is reality, no?
I ran my hands down her back, again trying to rub away any tension. “Let me help you to relax. Lie flat on your bed, and relax—on your stomach. Take off your shoes.” I kicked off my shoes as well. She was wearing jeans and a blouse. I guided her down and continued to massage her through her clothing. “How’s that feel,” I asked, “nice?” She said it was. After a short while, I told her she should start to undress more. She positioned herself at the edge of the bed, and I unbuttoned her blouse. I caressed her shoulder as I moved the blouse off of her shoulders. Once her blouse had been removed, I guided her back onto the bed. In no time, I unclasped her bra and pulled it out from under her, allowing her to indulge in her modesty for a while longer.
I asked if she had any oil or powder so I could continue a massage, but she didn’t even have cooking oil. I just made due and kneaded her more than rubbed her. I squeezed her neck and shoulders and worked down the length of her back. When I got down to her waistline, I asked her if she was ready to remove her jeans. She was, and she raised her bottom to unbutton them and loosen the zipper. I took over from there, working them down her legs and off of her. I removed her socks and rubbed the length of her legs. Time was ticking, but I maintained my deliberately slow pace. I rubbed her ass through her panties. I was surprised to see that they weren’t granny undies, though they weren’t Victoria’s Secret either. I kneaded her buttocks for a while longer and every so often returned attention to her back and shoulders.
Before I removed her panties, I took off my shirt, socks, and trousers. Still face down, I asked her if she was still nervous as I kneaded her now bare ass. She was. I lay along her side and began to kiss her behind the neck and ears, to which she responded positively. I asked her to roll over when she was ready, so she sat up.
I complimented her again: “Nice. Are you telling me I am the only other person to see like this was you mum when you were a child?” I fondled her breasts and without skipping a beat I took a nipple into my mouth. “Such a waste.” I pushed her back onto the bed keeping my mouth on her breast. I switched breasts when she was completely down, and I slid my hand down her belly into the tangle of her pubes as my finger found her slit. “You feel excited,” I told her as I felt her moist pussy. My finger was moist with her own juices—sort of—, as I continued to rub up and down the valley between her thighs. She was still nervous, but somewhat less so than when we had started. I asked her one last time, “Are you ready?” She was.
I removed my own underwear as I kissed my way down her belly. She had a full dark bush. She definitely didn’t shave or even trim her pussy, though she did touch up her under arms and legs. I guess she wasn’t expecting guests. I parted her thighs and began licking her vulva. As I progressed, I asked intermittently, “How’s that?” She just responded with, “uh huh.” She tasted good. I explored her fully with my tongue before focusing my attention on her clit. I stopped talking as I concentrated, running tiny circles around her clit while I began to work my thumb into her pussy along the way. I glanced up now and again to see how she was doing and at times reached up to fondle a breast or roll a nipple between my fingers.
Let me admit here and now that her appearance was the last thing on my mind. I was already fully hard as I anticipated her orgasm. It probably wasn’t much more than five minutes when she came, but when she came she just started bawling and sobbing. I asked her if she was alright or what was wrong, but she just kept crying, and I kept asking as I tried to reassure her. It was strange.
When she regained her composure, she told me that she felt like a real woman now—or something like tat—and that she didn’t think she’d ever be able to enjoy a sexual experience. I told her the pleasure was mine and gave her another kiss. I asked her how it was, and she said it was wonderful that she had never known it would be like that. When I told her that we had already been through that, she told me she had never had an orgasm before either. We talked a bit more and she admitted that she didn’t even masturbate. I told her that I’d be glad to help her gain some experience, and she was just beaming. I laid her back on the bed and went down for more. Skipping the details, she came again, and this time she didn’t end sobbing. It was my turn.
“I need to be inside you. Are you ready? Next time—and there will be a next time if I have anything to say about it—, I want you to use your mouth. Are you ready? Lie back.”
I spit on my cock and moistened her pussy a bit before I started rubbing the head of my cock along the entrance of her pussy. She was wet enough, I thought, but I wished I had some extra lubrication just to help her along a bit more smoothly. I worked my cock in as slowly as I could. She definitely had had no traffic down there. “Let me know if this gets uncomfortable. Are you OK? (and so on)” She was fine. A few centimeters deeper with each stoke until I was all the way in. I told her when I was all the way in. Once I reached that point, I relaxed and lay more fully on her, not holding myself up with my arms. My goal was to screw her slowly to allow the both of us to savour the moment. “You still OK?” “Mm hmm,” she moaned. “You are so tight,” I reinforced her. “Your pussy feels so wonderful. I’m going to want to make use of it more often.” She just moaned softly. When I was just about to cum, I thrust in as deeply as I could and pumped faster than before. “Next time you’re going to use your mouth. How’s that sound?” “Mm hmm.”
I remained on top of her still inside for a minute or so more before I pulled out slowly. We had been gone at least two hours, so I told her as much as it might be nice to stay longer, we’d better be getting going. And so we did.
On the short ride back, I ask her if it was nice, and she agreed it was. I asked her if she would like to call in sick the next day and make a day of it. After some discussion, she agreed that she’d take the next couple of days off, and I’d take just the next one—flu season and all.