My Sex Education Pt. 09

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."

"Mmm..." she moaned. "Yeah, stroke your cock like that. I like watching you stroke it. It's making my pussy wet. Have you seen her pussy? Is it as pretty as mine?" She tilted the camera even lower. Her robe had parted completely and she let it slide off her shoulders as she spread her legs a little, showing me her panty-covered pussy. She slid her fingers over the thin material, teasing us both.

"I... I don't think so," I moaned. "Yours is so pretty."

"Mmhmm... Now, you can't tell me that you don't want me to suck on that cock," she said.

"I do, mommy," I said. I remembered how good her lips felt wrapped around my shaft and my cocked throbbed even more.

"You want mommy to suck on it?"

"Yes... please," I moaned again.

She tilted the camera back up to her face, smiling at me. "Say it again. Say it again, baby."

"Will you suck on my cock mommy?" I begged her.

"Mommy definitely knows how to do that, doesn't she?" she asked. "And she loves it." She knew how much I loved her playing with my cock, either with her hands or her mouth. And my cock was really needy right now. "Does Sydney give you erections like this?"

"No mommy," I whispered.

"Do you want to feel her mouth on your cock or my mouth on your cock?" she asked, teasing me.

"Always your mouth, mommy," I said and I truly meant it.

"I know how to make you feel good, baby," she said, tilting the camera down again to show her fingers playing with her nipple. "Sydney's so young. She probably doesn't even know how to do it right. But I know how to please you, don't I?"

"Yes, mommy," I whispered again.

She tilted the camera back up again, just showing her mouth, and slid her fingers inside, sucking on them as if they were my cock. "Do you think a young girl like Sydney would even know half of what I know about pleasing you?"

"No."

She tilted the camera back down again, even lower this time, showing her panty-covered pussy. Her fingers slid under the material beside her pussy and pulled it, exposing her luscious, swollen lips to me. "Do you think she could even understand how much you love mommy's pussy?"

I shook my head. "I don't think so mom."

"Only I know how much you love this pussy," she said, her fingers sliding between her swollen lips, sliding up and around her clit. "And look, baby. Look what you've done." She held her fingers up to show me how wet they were. "You've made mommy's pussy all wet. So very wet. You know what that means, don't you?"

"Yeah," I moaned, licking my lips. My hand moved even faster up and down my cock as I stared at her wet pussy on my phone.

"We can't leave it like this, right?" she asked. "I have to get off. Be a good boy and keep stroking yourself. I like watching you stroke your cock... especially when you watch me play too. You want this, right?"

"Yes, mommy!" I moaned, my hand moving rapidly up and down my shaft. I watched her fingers slide into her pussy again then slide out, covered in her wetness, and circle her clit.

We were both gasping and moaning as we watched our phones, watched the other touch themselves.

"How could her pussy ever be any better than this?" she asked, spreading her labia to show her pink insides.

"It's not mommy," I moaned.

"Oh baby... You don't want mommy to be all alone, right?" she asked, sounding needy. "You don't want to stop making me cum, do you?"

"No... of course not mommy," I said quickly. I don't know if I could ever stop making her cum.

I could hear her breathing harder, getting more and more excited as her fingers swirled over her clit even more rapidly. "We always make each other feel so good, baby. I love how you fuck me. You get so deep inside my pussy. Keep stroking that cock."

The camera shook a little, as if she was having trouble holding it. I could tell she was getting close to her orgasm as I watched over the phone. I wished I was in person so see this.

"Yes! Yes! Yes!" she panted and then her body shook as she came, drenching her fingers. "Fuck!"

I listened to her panting as she brought the camera back up to her smiling face. She looked so beautiful in her post-orgasmic haze.

"You're such a good boy for making mommy feel so good," she said softly. "I want to make you feel good, too. Go ahead, baby... keep stroking your big, beautiful cock for me. I love watching you do it. Tell mommy how good it feels."

"It feels... so good mommy... so good," I panted getting closer and closer to my orgasm. I could feel the pressure building up inside me and knew it wouldn't take long now.

"What can Sydney ever give you that mommy can't?" she asked, licking her fingers.

"I'm gonna cum," I panted as I felt the pleasure my hand was giving me peak. "Oh my God... I'm cumming!" I grunted as I felt my orgasm let loose, spraying onto my chest and abdomen, running over my hand.

"Oh... yes... that was so good," she said softly. "I know how to please you, baby. I know how to make you feel good. I always have. What you really need is me, right?"

"Yes mommy... I just need you," I whispered, trying to calm my breathing.

"We'll talk about this more next week, baby, when you come home for Christmas. Alright?"

"Yeah... that'll be good," I whispered, feeling so tired all of the sudden.

She kissed into the phone. "Bye baby. Dream about me."

"Bye mommy," I whispered, then ended the call.

*****

On Friday afternoon, Sydney and I packed up the car and started our four-hour drive for home. Her parents lived only about three hours away and were pretty much on the way.

"Evelyn looks so beautiful," Sydney said. I looked over and she was going through her social media on her phone. Hailey had posted a bunch of pictures of my year-and-a-half old daughter and she was going through them. "Hailey and Brent have some good genes."

I felt a little pang of jealousy when she said that. Evelyn wasn't Brent's daughter... she was mine. Hailey and I had the good genes. Hailey and I produced that beautiful little girl. But I couldn't say anything, even if I wanted to.

"Yeah... she is beautiful," I said, turning back to watch the road again. I started getting into the music and tried to forget about Hailey and Evelyn for the time being. After a while, Sydney put her phone down and just lay back to enjoy the ride.

An hour into the trip and I started to feel a little horny. Sydney had worn a form-fitting, stretchy dress that came down to mid-thigh and, once the car had warmed up, had tossed her coat into the back seat.

I laid my hand on her thigh and stroked it tenderly. She didn't do anything at first, just lay back as always. I slowly moved my hand higher, wanting to play, hoping against hope that she'd let me. My fingers slid between her thighs and I could feel the warm, soft flesh there, making my cock harden quickly.

As my hand began sliding underneath the hem of her dress, however, and got too close to her pussy, Sydney became defensive. She brought her hand down, grabbed my wrist, and closed her legs tightly together.

"Vince... no," she said softly, looking at me sternly.

"Why not?" I asked.

"Because, we're out in public," she said, getting a little angry at me. "Everyone can see us!"

"Who's going to see us?" I asked, feeling frustrated once again. "It's dark out and there aren't that many cars on the road. Besides, no one can see down between your thighs."

She just turned away from me, looking like I disgusted her or something.

Frustrated, I went back to driving and listening to the music. This wasn't the first time I was pushed away. It was so damn frustrating, though.

We didn't talk much the rest of the way home, we mostly just listened to Christmas music. When we got to her parent's house, we got out, grabbed her suitcase, and I kissed her goodbye before she disappeared inside. I didn't even get to meet her parents, although it was a little late... after 9pm.

I got back into the car and continued driving to my Mom's arriving a little after 10pm. I grabbed my suitcase and came inside. My mom was certainly happy to see me.

"Vince!" she squealed when she heard me come inside and ran out of the kitchen.

"Hi Mom," I said, setting my suitcase down to give her a big hug.

She gave me a quick kiss... not at all a motherly kiss... and then moved back. "Your room is all ready for you," she said. "Or... if you want... my room is ready for you, too," she smiled deviously.

I laughed. "My room's fine. Is Hailey here?"

"No, not yet," she said. "She's staying with Brent's family until Christmas day. She's making sure everyone in his family gets to see Evelyn. I have a lot of stuff in her room, so they can't stay here."

"Ok... Well, I'm going to get cleaned up and hit the sack, if you don't mind," I said, starting to walk up the stairs to my room. "I'm really tired."

"Ok, honey," she said, sounding happy to see me, but a little sad that I was just going to bed. "I'll see you in the morning."