Chapter 4: A Date and a Threesome

Later that week I was at the end of a cross-country practice session I glanced up into the grandstands—we started and finished our runs in the school’s stadium—and Regan Smith was there, presumably to pick up her two boys. After the kids headed into the locker room, I walked over to her and struck up a conversation.

Somewhere in that conversation I ended up asking her out to dinner. It wasn’t planned, but it felt natural in the moment. She said yes, Friday evening would be fine.

Somewhat excited, I broke the news to Susan when I got home.

“Huh,” she responded. “I guess those tits were too big to say no to.”

That was not what I had expected. Susan was always excited to talk about sexual prospects, and she had always been open to bringing new people into our bed, although we didn’t do it all that often.

That night, when we climbed into bed, she said, “Good night, then,” and turned her back to me and went to sleep. Contrary to the impression I may have given, we didn’t have sex every night, but this was the first time I had literally gotten the cold shoulder.

Friday came and when I left to pick up Regan, Susan was again brusque.

Dinner was good. Regan and I seemed to hit it off. Conversation ranged from the personal—her divorce with her ex-husband, Ed, was recent and I was her first date since—to politics and the world situation—we had no major disagreements on those scores.

But then, as we were drinking our coffee, she said, “Mike, I have to tell you. I like you. You’re a really nice guy.”

Suddenly my stomach dropped. Had I been misinterpreting what had been going on all evening?

“But with the divorce and all, my relationship with Ed being so painful, I’m just not ready to launch into another one.”

There it was.

“But I really need to get fucked.”

What?!

“It’s been ages since I’ve had a good fuck, and if you’re game for sex with no strings attached, I’d really like to take you home tonight.” She explained the boys were at her ex’s that weekend, and we would have the place to ourselves.

Needless to say, we cleared out of the restaurant as soon as we could get the check. Normally, getting the check seems to take forever, but that night it took an extra-long time.

I think I broke every speed limit getting to her house.

The front door had barely closed before we were locked in an embrace, a big wet kiss. It felt as if her tongue was halfway down my throat. She took my hand and dragged me to the bedroom, both of us shedding clothes along the way. Half-naked, we fell onto the bed.

More kissing, and I could feel her breasts crushed against my chest as I fumbled to undo the hooks of her bra. I finally got it unhooked, and she sat up and took off her bra. Those magnificent breasts swung free, capped with large round areolas and pert, pencil-eraser nipples. I pulled her down on top of my, taking one of those globes into my mouth, flicking my tongue around her nipple.

But Regan had other plans. She slipped down and starting tugging my pants and underwear down; I had unfastened my belt on our way to the bedroom. I lifted my ass so she could get them off, and my already erect cock sprung free.

“Oh, my,” she said gazing at my eight inches. “That’s bigger than I could have hoped. Ed’s was always a bit disappointing.” And before I knew it, she had it in my mouth.

She was a good cocksucker. Not as good as my girls, but I suppose she had less experience. She bobbed her head up and down, getting about half of it down her throat and flicking my glans with her tongue at the top of the upstroke.

Before long, I felt my orgasm start to build. And while I knew I was good for several shots on goal, I didn’t want to cum quite so quickly. So, I lifted her head off my cock and guided her to my mouth. We kissed again, and I rolled her over on her back and started suckling at her breasts. She moaned when I nipped at her nipples, so I took the cue and gently slapped the side of her left breast. She winced and then smiled.

I didn’t want to take any pain play further without talking to her about it, so started kissing my way down to the vee between her legs.

Her mons was covered with a triangle of hair, cropped short, but her labia were shaved. I delighted in the musk emanating from her slit, and I dove in. Normally, I like to work a woman up before going for her clit, but I figured she was already in heat, and I was right. I flicked at her clit with my tongue, and she shivered. I clamped my lips around it, sucking it into my mouth, and her legs clamped tight around my head in return as she let out another moan. She put her head back and closed her eyes, letting me go to work.

I slipped down a few inches and darted my tongue past her open labia and into her vagina, scooping up some of her juices, which were flowing copiously. She was delicious. I then slipped a finger, then two, into her, curling them up to rub her inner clit as tackled her pink bud again with my tongue. Within a few minutes Regan was squirming as one, then two, orgasms flowed over her.

Before she had a chance to recover, I was on top of her, slipping my cock into her sopping wet pussy. She moaned and threw her head back onto her pillow yet again as I stroked in and out of her. Another orgasm quickly followed, and I jetted a stream of cum into her shortly after.

Sweaty, I collapsed next to her.

“Good God, I needed that,” she said, leaning over to kiss me.

“There’s more. Just give me a few minutes.”

“You’re a dream come true.”

We snuggled, gently rubbing our hands over each other’s bodies. My fingers found their way between her legs, and I gently caressed her vulva with the lightest of touches. In return, her hand found its way to my cock and slowly started to stroke it back to life.

I was ready again in a few minutes.

“Mmmm, you are as good as your word,” said Regan, and then she ducked down and took me into her mouth, quickly bringing my semi-erect cock to full mast. She licked down the underside of my shaft and swirled her tongue around my balls. “Do you know what I’ve really missed?”

“No, what?”

“Anal. And I really want to feel this big cock in my ass.”

“Your wish is my command.”

“Good boy. There is lube in the nightstand.”

I rolled over to get the lube, and Regan positioned herself on her knees, face down on the mattress, her lovely round behind raised into the air.

I greased up my cock with the lube, and before I applied some to her rosebud said, “Warning, the lube is rather cold.”

“I’m ready for it.”

She jerked as the first drops of lube hit her anus, then I smeared it with my finger, circling her rosebud. Then I slipped a greased finger in, then a second. She moaned appreciatively as I worked them in and out, loosening up her sphincter for the cock that was to come.

When she was ready, lubed and loosened, I positioned my cockhead against her anus and pushed forward ever so gently. There was some resistance, so I pushed harder, and my head popped into her rectum.

“Oh, God, that’s nice!”

I pushed forward another inch, then another, slowly easing my whole eight inches inside her. Then I started a slow thrusting in and out, applying more lube as I went.

“Harder! Harder!”

At her command I quickened the pace, slamming in and out of her ass while her fingers rubbed her clit. She whimpered and bit her lip, but every time I slackened the pace she urged me faster.

“Oh God! Oh God! Oh God! Oh God!” she exploded in orgasm. And at that moment I let go, sending jets of cum into her ass.

Once again, I collapsed beside her, and we snuggled. We were silent at first, gently caressing each other, then she spoke.

“You’ve done that before.”

“A few times, yes.”

Suddenly she got serious. “I want to do this again with you, but I meant it when I said I didn’t want a serious relationship.”

“I’m fine with being friends with benefits.”

She smiled. “You’re really a neat guy. If I was in a different place right now, emotionally that is, I’d want you as a keeper.”

“Thanks.”

“I mean, you were so understanding about my boys. Most teachers would have freaked out, made a big deal about it.”

“I’m used to teenagers. They’re hormone bombs. Boys especially, they’ll fuck anything that moves. Girls too, although they’re usually a bit more circumspect.”

“But seeing two brothers having sex in the locker room, that must have been a first.”

“Yes, the first time for that, but I’ve seen things just as outrageous. And sibling sex is more common than you might think. But I’m just as surprised that you took it so well. Most moms would have been screaming at them and dragging them to a psychologist.”

“You don’t think they need a psychologist?”

“Some kids, definitely. Your sons, no. They just need to get laid.”

She laughed. “I’ve got a confession to make.”

“Do go on.”

“I wasn’t so freaked out because that’s happened with me. Not gay sex in a locker room, but sibling sex. My first time was with my brother, Jim. I’ve never told anyone that.”

“Oh, I’m glad you feel I merit the trust. Your brother took your virginity?”

“Well, we didn’t actually fuck. But we did pretty much everything else, oral, mutual masturbation, the lot. And it wasn’t all the time, just a couple of times when we were teens.”

“That does explain a lot.”

“Who was your first?”

I wasn’t about to say my mom. Despite her confession, I felt that was a bit too much for a first date. Horny teen siblings were one thing, parents and children quite another.

“Her name was Spencer Rolland; we were sixteen.” That wasn’t exactly a lie. Spencer was the first girl I fucked besides my mom.

“Was it good?”

“It was nice, but a lot of fumbling and inexperience.” Now, that was a lie. It was a great fuck because I knew what I was doing. Mom and Dad had taught me too well. I didn’t like lying, so I changed the subject. “Ever thought of giving your brother a booty call now that you’re divorced?”

She blushed.

“The thought had crossed my mind, but only in a masturbatory fantasy. I would never do it.”

“Why not? You’re consenting adults.”

“Let’s change the subject. It’s getting a little too weird.”

“Okay. Ever been with a woman?”

She laughed. “Touché. No, I’ve never slept with a woman. But I’ve always been a bit curious about what it would be like. You?”

“Yes, I’ve slept with women.” She poked me in the ribs. “Yes, I’m bisexual.”

Her eyes widened. This evidently surprised her.

“I never would have guessed.”

“I prefer women, and romantically I’m only into women. But I’ll happily fuck a hot guy.”

“My brother is bisexual too.”

“Maybe we should have a threesome,” I said smiling. “Is he good looking?”

“Very,” she said laughing.

That’s how I planted the seed of familial sex in her. To be fair, it was fertile ground that had already been plowed by her brother years before.

I got home late that night. Susan was sleeping in the girls’ room. It looked like they had had a fun night. So, I went to my bed alone.