Too Good To Be True Ch. 29

"So, Brin..." Courtney asked, turning to converse with the present bodyguard. "You want to try sex with Tom, don't you?"

"Well... eventually, yeah," Brin admitted, blushing furiously.

"Anything you're hoping for the first time you try it?" Courtney asked with interest.

"Well, I don't want it to be shit," Brin admitted bluntly. "I don't know how many stories I've read about how... it... can be amazing and rock your world, but my mom always said it was just to make your man happy. My sister said that too, the only time I ever talked to her about it."

"I don't think that will be a problem with Tom," Courtney assured her. "Anything else?"

Brin thought about it. "I don't think I want anybody watching. That's a touch weird to me. Maybe I'll get into it, some of the girls definitely did, but... at least for the first time I want to be able to relax and I won't be able to do that if I feel like I'm performing for a crowd."

Courtney nodded.

"I just want my man to have a spine." Elaina threw out. "How can I respect any man I can push over? My mama may still bend her grown sons over her knee when they need it, but my papa can bend her over his knee when she acts up. And she knows it, so I've only seen it happen once. That's what a real couple is, a strong woman and a stronger man."

I was taking notes on my phone. Cause, fuck, it sounded like Elaina wanted me taking charge in the bedroom and spanking her if she challenged me, which was definitely NOT my go-to. Brin just sounded like she wanted a nice, peaceful first foray into lovemaking, and that was something I believe I could easily manage.

"I don't really even know what I'd want in bed," Parker admitted. "But... I like the idea that you definitely know your way around pleasing a woman. It's nice, feeling like I can let you show me how to enjoy it."

So Parker and Brin sounded like they were both just looking for a nice introduction to the world of sex. I could definitely handle that. From there, we'd mess around and find out what they really liked. Sometimes people's kinks shock even them.

The fabric of Courtney's dress wasn't super thin, but I began to notice a faint dimple where her nipples indicated that she found the thought of me breaking these new girls into the harem sexy. God, who could ask for a better girlfriend? Literally lined up as many hot young women as she could for me to break in, and teach what sex was like, and she just wanted a front-row seat and plenty of chances to be the one in my bed.

I leaned down and kissed her gently. I could feel her breath catch as our eyes met.

"Kiss me like that again, and my panties won't make it home on my body." She teased, then pulled me down for another kiss.

I took the hint and slid my hand up her thigh, caressing and slowly teasing my way until I reached her panties. The lacy lingerie thong told me this wasn't anything she hadn't planned on, and I bore her down on the full, couch-like seat.

"Damn, Brin, why do you get the good seat for this...." Parker grumbled, stretching her neck to get a view of her employer and future lover getting it on in the back seat.

Brin just smiled and leaned back. "Hey, you were the one that said the ranking member got shotgun."

I was too busy slipping the straps of Courtney's dress from her flawless shoulders. The built-in bra for the dress meant I didn't have clasps or anything else to get in the way, so once her breasts were free of the fabric, I kissed down her neck before latching onto her hard, excited nipples. I swirled my tongue around the sensitive bud before pinching it lightly with my teeth and giving a tug.

"Oh, fuck." Courtney moaned as her body responded. She lifted her hips and shimmied the dress over her hips, eager to get it out of the way.

I slid my hand down her stomach to her panties, even as the fabric of the dress we'd just bought flipped off her feet and fell to the floor. She was really getting worked up and was already starting to soak the lacy garment. My fingers slid around the edges, teasing her folds as I played the length of her womanhood. I held her pussy in my hand as she whimpered, arching her back in order to place her breasts skyward. She knew what I did; she knew what she liked, and she knew that sometimes, I liked teasing her before I gave her what she wanted.

She liked thin thongs, ones that were barely wide enough to cover her slit, and this pair was no exception. As I teased her, the fabric slipped between her folds, giving me an easy way to tease the bits of her that were, yes, enjoyable, but not the most sensitive parts. Nothing that would make her cum, just enough to really get her juices flowing.

Her breasts I ravaged. Lashing my tongue over the supple domes and teasing the nipples that begged for attention. I alternated which breast got the attention of my mouth and which was massaged and squeezed by my hand as Courtney moaned and whimpered in turn, loving what I was doing to her tits but desperately wanting more for her pussy.

Her hand scrambled to undo my belt, as her other hand was trapped on the far side of her body. Once undone, she quickly undid the button and zipper and didn't even bother to pull the pants and boxers down. She just dove in to start stroking my cock, making sure it was ready to cash the check my fingers were writing. Fuck, I loved that, and she knew it. It was one of the problems of having a partner who knew you so well. She knew full well I wasn't going to waste a load jizzing in my pants. And by revving my engine, she knew I'd have to move up the timetable for her.

Fine by me.

I grabbed the bit of thong between her pussy and asshole and pulled it down her legs before tossing it on the floor. Fuck, her hand was going hard, doing everything she knew I liked, so I had to reciprocate. I speared her cunt with two fingers, finding the bumps of her g-spot with ease after the number of times I'd played with that spot in the past. My fingertips began pinching her pussy, my thumb on the outside swirling her clitoris, and the other fingers inside matching the rhythm on her g-spot.

"FUCK!!!!" she screamed as her first orgasm rocked her, and bought me time as her fingers forgot their job and just clung to my cock as conscious thought left her head for a moment.

I took my role as an orgasm distributor quite seriously. That was essentially my role in the harem. I made sure all the girls who had joined got fucked as often as they wanted and were completely satisfied. I took my role seriously. I knew I was gonna cum, all of the members of my harem were amazing in bed and didn't have to try too hard to keep me happy. Though some of them made sure I knew they were going to try. Sarah took that job most seriously. Sometimes Sarah had to be stern and make me behave and let her take charge so she could treat me to a fabulous fucking. In my role as the orgasm distributor, I'd learned how to make my lover cum quickly, and of all of my lovers, I knew Courtney's body and what she liked the best. The feel of her g-spot, the spots deeper in her pussy that my fingers or cock could drive her nuts, the feel of her clitoris, they were familiar to me. Exploiting my knowledge, Courtney's orgasms came hard and fast.

"Fuck it, Tom... If we get home and I don't have a dick in me yet, I'm going to be upset." Courtney moaned as her legs stopped shaking.

"Better get in her quick... I give it another ten minutes." Elaina laughed.

Well, that was as good a directive as any. I shifted onto the seat between her legs, shoving my boxers and pants down, before lining up and drilling into her well-prepared and very lubricated sex.

"Oh yeeeeeeeeessssssss..." She groaned as I stretched her high heels back toward her shoulders and started thrusting. "Yes, yes, yes, yes..." She started groaning as my dick hit that perfect angle.

See, while some people thought you just pinned a girl's ankles behind her ears, assuming she was flexible enough, but nope. You have to find the right angle for her. Too far, and while it might make that pussy nice and tight for you, it won't be as good for her. It had taken us some serious time to find the right angle, but damn, it drove her crazy. After not even a minute of pistoning her love tunnel, she was cumming so hard she'd started squirting and I didn't even care that my white button-up was getting soaked.

"Oh! Tom! I want to feel it! Cum in me!" She pleaded.

Like she had to ask. We both knew that was happening and that she was prepared for it. And the way her pussy pulsed while squirting made it almost inevitable. I dropped my grip on her hips, thrust in deep, and let loose. Each stream of cum hitting her cervix made her legs shake, and Courtney grabbed my tie, pulling me down to kiss, our tongues embracing as my seed filled her sex.

"Bump!" Elaina called, and as we looked at each other in a 'huh?' sort of way, the car bounced, driving me into her once more. "And we're home."

"Fuck... I'm not done with you yet," Courtney breathed. "Your room. Fast!"

Courtney pulled on her dress, not bothering with the thong, and I pulled my pants back up so we could run to my room. For the first time, I lamented how big these mansions were.

When we arrived, Courtney pushed me back on the bed, pulled my shoes, pants, and boxers off as I pulled off the coat, tie, and shirt, then wrapped her lips around my cock, shrugging off her dress once more as her tongue swirled the head of my dick. I had lost my erection to the climax and the run across the mansion, but after moments of the pulsing, sucking bliss that she said was just her 'sucking on my dick like a straw,' my erection returned. She looked me in the eye and drove my dome to the back of her mouth, then swallowed it down her throat.

I couldn't do anything but moan. Holy fucking shit, she was good at that. Her tongue darted out to lick my balls as she made her throat pulse around my dick.

"Damn, you are so fucking sexy when you do that." I groaned.

"Well, you did teach me what you like." She purred, popping off my manhood. She mounted me, carefully lining me up before sinking herself hilt deep into my rod. "Mhm, I love that so much..."

She started rocking forward and back, almost going so far as to let my dick slide out of her, before thrusting back to take every inch again just before she lost me.

"I love seeing you fuck these girls." She purred. "It's like getting to watch you fuck me, but I'm helping them too... But fuck, this dick... this dick is mine and I love it."

"You know you could end it all now and you'd be the only one to touch it ever again." I moaned, feeling her cervix kiss the tip of my dick.

"What a waste that would be, though." She groaned. "As much as I wish I could, I can't handle getting dicked 24/7. So why not let you have fun when I'm done? Oh... fuck...." She trailed off as an orgasm shook her again.

I knew better than to argue. She wanted me fucking all the girls in the harem... and while I still offered; I knew I would miss it if I had to stop. So instead, I just groaned and enjoyed the sensation as she switched from the rolling thrusts to circular gyrations.

"Oh, fuck... Tom.... I'm...." She whimpered. Another rush of moisture bathed my hips as she squirted again.

She collapsed on top of me, and I held her close as we both descended from our sex high. Her body shook as the orgasm echoed through her, and my body slowly got feeling back in my toes as my erection faded and slipped out of her.

"Mhmmmmm... I love you so much." Courtney breathed.

"And I love you too," I affirmed and kissed her again.

"Is it weird that I want to do a threesome with Cindy while we're here?" She blurted. "I mean, she's gonna be my sister and all, once we get married, but damn. She's cute."

I laughed. "I mean, we've gotten pretty close before. We just weren't crossing the sex line. You'd have to talk to her about it."

"Later," Courtney murmured and nuzzled up in my arms. "I just want this right now."

We cuddled naked for almost an hour before Courtney got up. "I know it's stupid, but I like my mattress better." She admitted. "I'll see you in the morning." She kissed me and walked from the room, picking up her heels and dress as she left.

Not a bad day, I thought to myself. It might be early, but I was content to turn it in. I used the remote to turn off the lights and drifted off, not even caring when one of the girls slipped into bed naked with me. I could feel her bare skin against me, and as we cuddled, my hand naturally landed on her breast, not really groping, but just holding whichever of my girls it was, as I drifted into oblivion.