Part 2.
It turned out we had gone to school together, Desiree, the newest dancer at the club where my mother worked, but I don't remember seeing her before. Cute girl, maybe 5'1 to my 5'11, narrow waist and nice hips, especially for just being 18 like me. Turns out she is as shy as me, too. She looked up to my mother as a mentor, and definitely someone who could teach her how to make it and stay safe working in the clubs downtown. She had just started to learn to pole dance a little, but my mother said she picked up the basics quickly.
My mother arranged for us to meet each other the first time over lunch in a cute little café downtown my mother knew about. The first thing I noticed was her eyes, light hazel brown that absolutely lit up and made me blush when she smiled at me. Sitting at that little café I felt butterflies for the first time. I probably admired her cleavage a little too much, making her blush back at me.
After lunch she gave me a little hug and we agreed to hang out again soon, which turned out be just a few days later. We both started to open up to each other more and more with each date. We both were raised by single mothers but she had brothers, one older and one much younger. She really needed the money from working in the night clubs to help her family, but she didn't want to have to do that forever. She told me how much my mother helped look out for her.
For six months we dated, seeing each other once or twice a week, slowly building our relationship. At the end of each date she would usually give me a little kiss on my neck or my cheek but we hadn't progressed to anything really physical yet.
I didn't rush her. After all, I still had my mother at home. Since the first time we had sex together, it had opened up a new dimension of our relationship that could never be closed. On my mother's days off, once or twice a week we would spend a lot of time intimately together in her bedroom, which she now welcomed me into. Just holding her body close to me always turned me on for her, and she had built up my stamina such that I could make love to her for almost an hour each round, and usually go for multiple rounds, however much she wanted.
I counted it up one time. Over the course of the first six months I dated Desiree, I must have sex with my mother at least a hundred times. But I had another woman in my life now, Desiree my girlfriend, and I felt more and more emotionally connected to her, and began to long to be intimate with her as well.
Finally after six months she invited me over to her place after our movie date. Neither of us really knew how to make out, we quickly discovered awkwardly. I never actually kissed my mother on the lips, although at time I would kiss on her body, especially my mother's amazing breasts that I worshipped. But cuddling up with Desiree on her couch, we immediately started to kiss. Her lips on mine felt so amazing, and how her hands eagerly explored my body... it felt so natural, and different, to hold her in my arms compared to my mother. But that night all we really did was kiss and hold each other until we both had to go.
The next day I told my mother about it. She grinned when I told her. I loved it when things I did made her happy. She asked me if I thought Desiree wanted to have sex soon. We hadn't actually talked about it, but my guess was yes, or at least I hoped it was yes, but as much as I wanted to start having sex with my new girlfriend, I didn't want to mess up the relationship my mother and I enjoyed.
"Don't worry, son" she reassured me. "We can still be intimate with each other as much as we want no matter who else you're with. It's your choice whether you want to tell her about us or not."
Clearly I did not want to reveal that to Desiree or anyone else, at least not any time soon.
"But even though you and I have had a lot of wonderful experiences together now, there are still some things you need to know" she began to explain.
Uh oh, I thought, are we about to have the talk?
"She might be a virgin, sounds like she probably is. That means you're going to have to be very gentle with her. You can't just push yourself in her like you can me, at least not until she tells you she's ready. And you absolutely cannot get her pregnant, ok?"
"Right, absolutely not" I agreed, well, not until we would get married someday maybe.
"So you'll need to use a condom. You can't cum inside her like you do inside me" she calmly instructed, looking me right in the eye so I would know it was serious.
"Ok but like, I've never used one before." I really hadn't. My mother and I never used protection. Why should we, since she had her tubes tied years ago. "Or what if she tells me she's on birth control?" I wondered.
"Lots of girls will say that when they're really not. She would have had to go get a prescription and start taking the right pill every day for weeks beforehand. You can't trust that, at least not right away. You'll have to use a condom every time you have sex with her, ok? We can practice using them together ourselves to get you ready."
"Ok mom, thank you. See you tonight." I replied, looking forward to being with her again.
That night we crawled into her bed as usual, with the fan whirling softly overhead and her soft music playing, just the way we liked it. As we peeled off the rest of our clothes and held each other naked I wondered what it would be like to kiss her, so I did, softly and lovingly on the lips, just like I had Desiree. To my amazement, my mother met my kiss with passion of her own, meeting my lips, then opening her mouth slightly to lick my teeth with her tongue, before plunging her tongue into my mouth to find mine. I gave in immediately, welcoming her into my mouth, the first French kiss of my life. The longer we held each other naked and kissed, the more I wanted to push myself deep inside her, to show her how much I loved her. I felt myself hard and throbbing, waiting for when she would climb on top of me or spread her legs wide for me this night.
But instead of rolling on top of me, she rolled over toward her nightstand and plucked something off the top of it by the lamp. She tore the edge of it open, and pulled out a fresh condom. I had never seen one before.
"Here, she said, it goes on like this." She held the tip of it above my penis before sliding it over my swollen tip. Inch by inch she rolled it down over my shaft, forming its necessary seal over me, until fully extended it stopped about two inches from the base of my shaft. The way she did it left about an inch loose above my tip. "That's to leave room for you to cum. That's important otherwise it could break or it will hurt when you cum. Ok, now you're ready."