My Sex Education, Part 9
Just two months after Mom's fiftieth birthday, two months after I last fucked Hailey, Hailey found out she was pregnant and it rocked my world. We both knew that it was mine, and we both struggled for a week about what to do about it. But, in the end, we decided that she should tell her boyfriend that it was his. And then just two months after that, she and Brent, her boyfriend, got married at the courthouse.
I have to say, I was a little torn. That was my baby girl. I wanted her as my own daughter, not pretending that she's my niece. But I didn't have a lot of say in the matter. It would have been very bad if the world found out about us. Especially about us with a baby girl.
Now, it was two years after my mom's fiftieth birthday and I was dating a new girl now, Sydney. Ashley and I parted ways, just not seeing eye to eye on things, and she got a big job out west to which I really didn't want to follow her. It wasn't a difficult breakup, really. We just kind of said goodbye.
So then I started dating and met Sydney. She was a really attractive brunette, with brown eyes... about 5'5"... with C-cup breasts that I loved to play with. When we first started dating, she was so receptive to my sexual advances and appetite. I mean, my Mom and Hailey showed me so many things about how to tease and please a woman. I had to try them out on her. But as time wore on, she seemed to be getting tired of it for some reason. She started telling me no more and more often, coming up with lame excuses. Still, I had thoughts that I should marry her. I thought that maybe that was the problem... she thought I only wanted her for sex.
She and I had already made plans about going down to visit both my Mom and her parents for the week between Christmas and New Year's. Sydney's grandparents weren't doing very well health-wise so I was going to drop her off at her parent's first, then come and bring her over to meet my Mom later in the week.
About a week and a half away from the trip, I called my Mom to talk to her about my plans to propose to Sydney. I wanted to get her advice and maybe her blessing.
"Hey Mom!" I said, when she picked up the phone. It was only about 8pm and Sydney was at work... again.
"Hey baby, how are you doing?" she asked. She always seemed so happy to see me or talk to me, even just on the phone. For the past two years, she's even been known to call to flirt or even a little phone sex. I guess that she was pretty lonely.
"I'm doing good. I just... I just have something on my mind that I wanted to talk to you about."
"That sounds serious," she said.
"Yeah, it kind of is," I said, trying to figure out how to tell her. I felt like I was abandoning her for some reason. Like I was pushing her aside for another model. I mean, I did want to run away with her when I first moved out, and she rebuffed me. So maybe it really was time to cut the cord. "Well, you know I've been dating Sydney for almost 2 years now."
"Yeah..."
"Well... God... I'm just going to come out and say it. I'm thinking about proposing to her," I said quickly.
"Wow... that's a pretty big step, baby," she said, sounding a little apprehensive about it.
"I know. That's why I wanted to talk to you about it."
"Well, I have to say, I'm not really surprised," she said. "We talked about this. I mean, I knew it was coming. You meeting someone and getting married some day. So... tell me about her? What do you like about her? Why do you want to marry her?"
"Oh... um... I don't know... she's nice," I said. Words failed me. I was having a very difficult time telling her how I was feeling.
"That's it?" she giggled. "That's all you got? I mean, marriage is a huge step."
"No... I know... I mean, she's smart and pretty," I continued. "She likes hiking... and plays tennis. We just... we really get along well together."
"Mmhmm," she said, sounding doubtful of my reasons.
"I don't... I don't know what to say," I said. "I thought you wanted me to find someone."
"Sure I do," she said. "That's what every mother wants for her son. Right? And I want that for you, too. I just want to make sure this is the right girl... not just any girl. I mean, I just want to make sure you love her and aren't just wanting to be with her for sex. I don't want you to get into a marriage that ends up like your father's and mine."
"I... I don't know. How do I know if it's love or not?" I asked. "It feels like it is."
"Baby, you know what it's like when just you and I are alone, right?
"Yeah?"
"Do you like that?"
"Yeah, I like it a lot," I said.
"Yeah? What we have... is... really deep. It's much more than just mother and son... or physical attraction... or sex. What we have is a really deep connection. Right?"
"Yeah, I think so, too."
"I really like the special moments that you and I have together," she said. "I hope you appreciate them too."
"I do mom. I really do," I said.
"That's love baby," she said. "Really deep love. Are you bringing her for Christmas this year? So I can meet her?"
"Yeah... of course," I'm dropping her off at her parent's for the first half of the week. She'll be over on Wednesday."
"Ok... ok... I'll see for myself how you two feel as a couple," she said. "I mean, meeting new girls is important and great and all... but what you and I have, our bond, is special. Right? It's lifelong."
I nodded, although she couldn't see it. "I think so, too."
"And I always know how to make you feel good, don't I baby?"
"Yeah," I smiled. She always did make me feel good. Suddenly my phone made some strange noise and I realized that she started up a video call. I pressed the button to accept it and held the phone up so she could see my face.
"Wow... you look really good," she said.
I could see that she was wearing her black, satin robe that I loved so much. It made her look incredibly sexy. I briefly wondered if she was going to bed early. In contrast, though, she was wearing makeup and her hair was elaborately coiffed. "You look really good, too, mom."
"Aw, thanks. I like how you're always complimenting me," she said. I smiled. I always enjoyed making her happy.
"Are you going out somewhere?" I asked.
"Oh," she smiled, touching her hair. "No, just going to work a little."
"Work? You got a job?"
"Yeah, I found something. But don't worry, baby," she smiled. "I'll tell you all about it when you come to visit. Right now, though, I'm kinda wanting one of our special moments," she smiled deviously.
"Now?" I asked, not exactly sure what she was trying to say.
"I assume Sydney isn't there?" she asked.
"No... no, she's working tonight."
Mom licked her lips a second. "Why don't you show me your cock?" she asked, surprising me. "Go on... show mommy your cock, baby. Pull it out."
I slid my sweats and boxers down, throwing them to the floor, which was quite difficult one handed, and then tilted the phone down, showing her my erection.
"Mmm, that looks... really good," she said, almost yearningly. She licked her lips again as her hand disappeared below the camera's view on her side. I guessed she was caressing her breast and teasing her nipple. "Stroke it. Yeah... stroke it."
I slid my free hand up and down my shaft, then grabbed the bottle of lube and applied a little to make it work better. When I went back to stroking my cock, she moaned softly.
"I like watching you stroke it," she said.
"Yeah," I moaned.
"Are you feeling good, baby?" she asked, smiling. "Am I making you feel good now? You like the way that feels, don't you?"
"Yeah... it feels good," I answered. And it wasn't a lie. It felt really good right now. My cock was throbbing to hear her talk to me like that. And with Sydney denying me a lot more, it had been a while since I'd had an orgasm. That was the reason the lube was so close. I was already getting prepared to watch some porn and masturbate.
"You like my titties?" she asked as she tilted the camera down a little, putting her breasts on display as she opened her robe. "Does that make your cock even harder? Does it make you harder when you look at my tits?"
"Yeah... God they look so good." Her breasts always excited me and made my mouth water. I loved how big they were and the way her nipples got hard and pointed.
She used her free hand to grab and squeeze each beautiful mound, gripping her nipples between her fingers to squeeze, roll, and tug on them, for her pleasure and mine. God it was so hot.
"Sydney may be cute and smart," she said, teasing me. "But do her tits even compare to mommy's?"
"No... her boobs are much smaller," I said.
"Not like mommy's, huh?"
"No, mommy, they're not big like yours."
