Colton came to us in an unusual way. Normally we get referrals from friends and friends of friends. This time it was Colton's dad who contacted Julie, my twin sister, and partner in our "My First Time" escort agency. His dad worked with Kathy Anderson, a good friend of ours, in the tech industry.
Colton was a virgin. According to his picture, he's a hunk that any girl would love to sleep with. But he's also painfully shy around women. He was about to go off to UCLA on a football scholarship, and his dad didn't want him to be taken advantage of by aggressive college girls. Thus, the need for our services.
I recognized him the moment Colton entered the restaurant. 6'2", dark, wavy hair, muscular body - but with kind, dark brown, eyes. I waved him over. He was wearing a cotton button-down shirt and khakis.
"Boy, this place is hard to find!" he said, sitting in the seat across from me. "You must be Donna," he said, extending his hand politely.
"Nice to meet you, Colton," I said, taking his hand. It was surprisingly warm and soft. "Cherry Coke, right?" I said as the server magically set the soda down in front of him.
"How'd you know that?" he asked.
"Trade secret," I said, smiling.
In reality, our research into each client is pretty exhaustive. By the time we sit down at our out-of-the-way restaurant, we know their bio, habits, likes, and desires.
Colton was about to lose his virginity to me, and I wanted to make sure this shy guy got the absolute best experience possible.
"I'm a bit nervous about this," Colton admitted, taking a sip of Coke, and setting his glass down.
"That's why I'm here, Colton," I said. "I'm an expert in helping men and women through their first-time sexual experiences. Together, we're going to do just fine!"
Colton seemed to relax a little. "You sure are beautiful!" he said.
"Thank you! I'm flattered." I was a good 12 years older than Colton, but hoped my long auburn hair, sexy legs, slender body, and D cup breasts would attract this high school graduate. It appeared so.
"So, what's your biggest fear about having sex?" I asked. I rarely beat around the bush with my clients.
Colton hesitated for a moment, as if thinking. "I guess it's that I don't know what I'm doing. I mean, I've seen some porn and hear the guys talking about their conquests in the locker room but..."
"Well," I said, laughing. "Forget anything you've seen in porn - it's really just sport-fucking. And your friends haven't done half the things they boast about!"
"Okay!" Colton said, laughing with me.
"And you've not had any experience yourself?" I asked.
Colton shook his head. "I've kissed some girls but that's it. I haven't really had time anyway with athletics taking up most of my year. And besides..."
"You're kind of shy?" I asked.
Colton nodded, a little embarrassed.
"No need to worry, Colton," I said, placing my hand on his. "By the time you're done making love to me, you'll be so much more confident that the shyness will melt away!"
"I'd like that," he said.
"See, Colton, it's not just about you having sex for the first time. I'm going to teach you how to please a woman, and please yourself at the same time. It's going to be fun getting to know each other's bodies!"
I noticed Colton glance down at my chest. I knew what was happening. As I started to imagine Colton naked and his cock entering my pussy, I could feel an itchy feeling in my crotch and was sure my nipples were beginning to get engorged. I wore a clingy top just so they'd easily show through.
"I hope you like what you see," I said. "'Cause you're going to be able to do a lot more than just look at my tits!"
Colton looked up, this time a look of desire on his face.
"Want to continue this conversation back to my place?" I asked, squeezing his hand slightly.
Colton nodded. I quickly texted my driver to meet us out back. As we stood, I ran my fingers along Colton's chest and noticed a bulge in his pants.
"I think you're already thinking about what it's going to be like," I said, nodding to his crotch.
Colton blushed a little, but nodded.
We took places sitting across from each other. I did this on purpose as I knew my short skirt would ride up so Colton could get a peek at my pink lace panties, and the wet spot beginning to develop on them.
The screen between the passenger area and the driver, plus the tinted windows, made the journey to my house very private. I rested my hands on his thighs as I leaned over and gave Colton a kiss on the lips. His lips were also pretty soft, though not as soft as a woman's.
"Okay so far?" I asked, moving away just slightly.
"Very much!" Colton said, pulling me back in.
This time I touched his lips with my tongue. He opened and let me in to explore his mouth. The meeting of our tongues sent pleasure feelings down to my crotch and served to further wet my panties.
As I sat back, I took ahold of one of Colton's wrists and moved his hand to my chest, placing it on one of my boobs.
"A woman's breasts are very sensitive," I said, "especially the nipples. Why don't you touch mine?"
Colton ran his index finger over one of my nipples.
"Ooh. That's right. Now squeeze it. Yes! That feels so good!" I said. "See how much I'm wanting you?" I said, opening my legs.
His eyes fell to my crotch as he continued to fondle and tweak my nipple.
"Why don't you touch me there?" I said, glancing down. "I really want you to."
Colton removed his hand from my breast and tentatively moved it between my legs. He grazed his index finger on my pussy. I shuddered at his touch.
"Is that okay?" he asked.
"Oh yes," I said, pulling his hand back to my crotch. "It sent shivers through me to have you touch me."
"My finger's wet," he said.
"That's my pussy juices," I said. "It means I'm getting very aroused at the thought of you entering me with your cock!"
"Wow!" Colton said, stroking my wet panties.
"I think you're thinking about it too," I said, nodding to his pants.
Colton looked down, shifting himself slightly to allow for a growing erection. "I am!" he said. "Do you want to touch me?"
"In the worst way," I said. I reached over and ran my hand down the length of his hardening cock. Colton practically jumped in response. "Feel good?"
"Fuck!" he said. "Feels... wow!"
I came back over, and we made out, more deliberately this time, tongues trading mouths back and forth.
In a few minutes we reached the house Julie and I keep for business. It's in a secluded neighborhood and the driveway is shielded from the road and the neighbors.
I opened the door and ushered Colton in. The house was dimly lit by candles that Julie had placed in the living room and in the bedroom. Soft music played from hidden speakers and a fire crackled and threw shadows on the wall.
I drew Colton into the living room, and we sat on the couch.
"Wine?" I asked, picking up a chilled Syrah that Julie had left out.
"Um, sure!" Colton said as I poured two glasses.
"To new beginnings!" I said, clinking my glass with Colton's.
"This is really good!" he said, taking a sip.
I took his glass and set both on the coffee table. I put a hand on his thigh and with the other cupped his face, coming in for a deep French kiss. My hand wandered until it was again stroking his manhood. I could tell Colton was gifted in that area and I couldn't wait to get my mouth and my pussy on his dick!
"I can feel your dick getting larger," I said, breaking off. "It's going to feel so good for you to be inside me!"
"I'm really looking forward to that!" Colton said.
"I think it's time you got to know my breasts a little more intimately," I said. "Why don't you take off my blouse."
I lifted my hands and Colton grabbed the silky fabric, lifting it over my head and exposing my pink, nearly sheer bra. His eyes fell once again to my chest. I knew my large nipples and areola were showing through the fabric.
This time Colton didn't hesitate but reached out with both hands to touch my boobs and play with my nipples.
"That feels so great!" I said, my hand going back to kneading Colton's cock through his pants.
"Why don't you kiss them?"
Colton looked at me, then leaned down and lightly kissed one nipple, and then the other.
"Now lick them through my bra," I said, stroking his wavy hair.
I watched his tongue flick out. When it touched one of my nipples, I felt a flood of pleasure in my breast, traveling down to my pussy.
I reached my hands behind my back and undid my bra. Colton leaned back up as I let it fall off my chest and onto our laps. My large breasts were now free and freely on display for this young virgin. He stared at them, bouncing slightly, my nipples hard and sticking straight out.
"This is really happening!" he said.
"Oh, it is," I replied. "My breasts are all yours, Colton."
I pulled his head to my chest. He opened his mouth and took a nipple in, licking it and twirling it with his tongue.
"Now suck on it. Suck on my nipple, Colton!"
I felt his lips purse and my nipple being sucked up into his mouth. The feeling was incredible. My chest rose in response, and I felt tingly all over. The itchy feeling in my crotch was getting more intense.
"Shit, Colton. You're sucking my tit. Oooh, that's good!"
He moved to the other one and sucked on it, while squeezing a nipple in his fingers.
"Your tits are amazing!" Colton said, sitting back up. "They're so big and hard!"
"I'm turned on by you, Colton. You're turning a woman on!"
"Shit!" he said, smiling.
"And we've only just begun," I said, standing. "I want you to know me intimately!"
I undid my skirt and let it fall to the ground, kicking off my heels in the process. Now I was only wearing a pair of lacy and very wet panties. Colton looked me up and down, reaching out and holding my waist, stroking it slightly.
"Your skin is so soft and beautiful," he said, looking up into my eyes.
"Why don't you see what the rest of me looks like?" I asked, moving his hands down to the waistband of my panties.
He grasped the elastic fabric and slowly pulled them down, revealing my dark auburn bush, which was quite damp and glistened in the candlelight. I let him pull them down to my ankles. I stepped out of them and stood totally nude before Colton.
"Are you ready to touch me?" I asked.
Colton looked at my pussy and nodded. Reaching out a finger, he ran it through my bush.
