I pulled my finger out of her pussy and rubbed the juices onto her clit, and then slid two fingers into her pussy. I felt the walls contract around my fingers and I felt she her tightness grip my fingers. I pressed my fingers in further, and that’s when I felt it. I felt the resistance against my fingertips.
I pull out of her pussy, and cover her back up with her skirt. I drive on, licking my fingers. I marvel at the taste of her juices on my digits. I can’t believe it. My secretary is a virgin.
* * * * * *
When I near the city, I wake her up. She is drowsy and takes some time to wake up. As she stretches, she realizes her skirt has ridden up a bit. Without thinking about it, she pulls the hem of her skirt down. “We’ll check in first at the hotel and that’ll give you a chance to use the restroom and fix your make up if you need to. Unpack your things and such.”
“Okay, Mr. Henderson.” She lets out a small yawn. “Sorry,” she giggles, “I didn’t think that nap was going to be that good.”
“Yeah?” I ask, nonchalantly. “You are going to have a busy day, so be prepared.”
She nodded and then turned around in her seat, reaching to the backseat to her purse. She didn’t notice that her tits pressed against my arm and I had half a mind to reach over and squeeze those great tits of hers. She grabbed her purse and pulled it to the front seat. She pulled out a make up bag and touched up her lipstick and eye shadow. “I know you said I can do this in my room, but I want to look good when we get there. After all, I’m representing you and your company before myself, right?”
“That’s right….” I smile at her. “Here we are.” I say taking the exit into the small town. The hotel and club aren’t too far into the town and I pull up the drive way to the club. We are met by valets when we drive up to the front entrance and she gets out of my car. I walk up with her and she does her best not to spin her head around as she takes everything in.
“It’s just so beautiful here!” she gasps as we enter the lobby.
“Yeah, I would love to live here,” I said. “Of course, anyone who spends most of their time here will tell you about their multi-million dollar homes and treat this place as if it’s a Motel 6.”
I chuckle and she smiles. Denny, the head hotel manager, walks up to us and hands the room key to the luggage boy who is a few feet behind us. “Right this way, Mr. Henderson, I have your usual room, and I will let Mr. Clarkson and Mr. Garrett know that you have arrived.”
“Yes, thank you, Denny,” I say handing him a $50 bill and whisper in his ear so Rebecca can’t hear. “Thank you very much, Denny.”
Denny nods and walks away to the front desk.
We ride up the elevator to the third floor of the hotel and walk down the hallway with the luggage boy to our door. He inserts the key and opens the door, letting us enter. Rebecca is close behind me and the boy brings the luggage in. “Call down to the lobby when you need me to get the luggage cart. Anything else sir?” he asks as I begin to pull open the curtains for the glorious view.
“No, thank you,” I say. I walk away from the window and give him a tip. He exits the room and I close the door behind him, I turn around and Rebecca is standing next to the window, looking down at the golf course and tennis courts below.
“It’s beautiful here!” she exclaims. “And it has a pool?”
“Yes,” I walk up to the window with her. “And an indoor hot tub in the bathroom here.”
“What?” she looks at me. “Really?!”
“Go have a look,” I motion to the bathroom door. She bounces off to the bathroom and exclaims an ‘Oh god!’ I laugh. “Yes, I know, that’s why I always ask for this room. After listening to Greg and one of his many stupid and boring clerks, I always want to take a soak when I get back. I promise to be nice when deciding who gets to get in first.”
She laughs and comes out of the room. “Yeah, I’ll arm wrestle you for that at the end of the day.”
I smile and show her the suite. “Here’s the door to your room, I hope you don’t mind that you will be sleeping in a queen–”
“Oh shit!” she says as she enters her room. “Sorry,” she blushes when she makes eye contact with me. “It’s just….oh god,” she says looking around the room, “this room is bigger than my whole crummy apartment!”
“Really?” I ask, then shrug. “Well, you’ll notice we share the bathroom though, however, you have your own T.V., mini bar, closet, vanity…balcony.”
“Oh my…” she whispers. “I feel like I’m on vacation!” She looks back at me and her eyes start to water. She wraps her arms around my neck and hugs me. “Thank you, Carl…thank you….” she pulls away. “Oh, I mean Mr. Henderson.”
“No, it’s alright if you call me Carl this weekend.” I smile. “Just don’t hug me again in front of anyone here, they might think we are having an affair.”
She laughs and steps away. “Sorry, I’ve just never been to anywhere this nice before. Even my prom was at a crappy rec room at the Clarkson’s hotel back home.”
I chuckle again. “Well, get ready, Rebecca.” She looks at me stunned as I had called her by her first name. “Yes, for this one weekend only, you may call me Carl and I will be calling you Rebecca. It’s so Greg doesn’t know I’m still an uptight jackass.”
We smile at each other for a few moments and then there’s a knock on the door. “Can you get that, I need to unpack my clothes,” I tell her. She heads to the door and I go to my room. She opens it and Denny comes in with a push cart of different snack foods. Some sandwiches and soups and a plate of French fries with a sliced tomato.
“Mr. Henderson thought you might be hungry from the drive here, Miss.” He puts the cart in place by the bar in the living room and smiles at Rebecca.
“Thank you, Denny, right?” she asks.
Denny nods and waits to be dismissed.
I watch as she stands there awkwardly and looks at the food, then at Denny who just stands there. “Ummm, thank you,” she says again.
I laugh and come out from my room. “Thank you Denny, the food looks great.” I hand him another tip, “We’ll call you up this evening for warm towels.”
“Right sir, have a good day. And oh yes, Mr. Clarkson and Mr. Garrett are finishing up with their final round of golf and will meet you in the conference room in the lounge.”
“Thank you, Denny.” I close the door behind him and smile at Rebecca. “Well, let’s eat before we get to business. I told Denny that your favorite is French fries and a tomato.”
“Thank you, I’m so hungry.” She takes the plate of the fries and carries it to the balcony. “You want to sit out here with me while I eat?”
“No thank you, I really must get dressed for our meeting. You should change into your white summer dress and sandals, no need to over dress for today’s meeting. We’ll probably play tennis afterwards and you can come up and dress into what you have on then.”
“Okay.” She says and sits on the lounge chair and eats as she looks out over the view.
I watch her as I go through my briefcase and pull out my files. I watch her eat the fries one at a time. I feel the stirring in my pants as I watch her lips suck on the slices of the tomatoes and I remember how wet she was when I my fingers pressed into her body. I know she would certainly quit if she found out I had taken advantage of her while she had been sleeping in my car on the drive here, but I must know if she is a virgin.
Oh the times that Greg and I had in college together. We’d been in the same frat as James and been in a club that James and I and a few other friends had made. One night before I moved out of the frat after graduation, we went to a party one of the other frat houses were hosting.
There, we met up with his girlfriend who came if from their home town. She brought her friend from back at home. Greg’s girlfriend had accidentally let it slip that her friend was a virgin, and I wanted to talk to her friend at the party in private.
Greg’s girlfriend found her by one of the keg’s and dragged her over to us to introduce us. She looked just like Rebecca, she had long hair and dressed really skimpy. I was surprised to know that she was a virgin; she was showing off her tits through her tight top that was unbuttoned down to the crease between her tits.
I smiled at her when Greg’s girlfriend introduced us, she smiled at me with her face blushing. Once again, just like Rebecca.
Later in the night, when we were dancing, I held her hips in my hands and grinded up against her ass as we skillfully danced on the floor with the other students. She laughed along with me as we sang along with the song and I nibbled on her shoulders as we danced on. I knew she could feel my raging hard on through my jeans to her ass and when we left the party a few songs later, I knew she wanted to make out. I took her to the woods behind the frat house, taking her away from the loud music and shouts from the party goers.
I had been to the frat many times in the years I had been attending school and I knew of the pool house that belonged to the house that was a couple of yards away. The family that lived there only came during summer break when most of the college kids were at home. I had taken a job for the family of house sitting one semester and then forgot to ask me for the pool house keys when I finished the job for them. I slid the key in the door handle and turned it, relieved that they hadn’t changed the locks.
We went inside and I closed the door behind us. The pool house was big and spacious, and I pulled a sheet off of the stereo by the wall and turned it on to a station playing jazz. I then pulled off a sheet over the couch and had her sit down as she was getting tipsy from all the beers she had had. She smiled up at me and I began to pull off my shirt as I kissed her. She kissed be back and I got between her legs, pulling up the sides of her skirt to feel her smooth thighs.
She sighed in my ear as I began to suck on her neck and found my hands between her thighs, feeling the wetness that was soaking her panties. “Oh, Carl…wait…I’m a virgin,” she gasped.
I moved my face away from her neck and smiled at her. “I know…” I whispered to her. “Shhh….” I went back to kissing her neck and pulled her panties down her legs. She helped me to undress her, and soon, we were fucking on the couch. She yelped out loud when my cock entered her tight pussy and when I pressed my head through to her cervix and loosened her up, she cried. I held her face against my bare chest and rocked my hips back and forth as we slowly fucked away her virginity, and when I finished, I held her in my arms.
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