"Chloe. This might be the most unexpected and exciting proposal I've ever received. Are you sure it's not the alcohol talking?"
"It's not," she assured me, looking at me with the most beautiful soulful eyes.
"I mean, I'm at least thirty years older than you," I implored. "I used to be your boss," I added.
"But, you're not married and...well, at least not anymore. And I find you very attractive, Jake. We wouldn't be discussing this if I didn't feel something." I could see she was beginning to get upset. "Oh, God," she exclaimed as she put her face in her hands. "I'm so embarrassed. I shouldn't have...I'm so sorry," she said in a voice that sounded like she was bordering on tears.
It was true. I was not married, but I had been. I may have been a confirmed widower for the past seven years, but I surely understood marriage and all the negotiations and compromises that go into a good one. But at this moment Chloe was distraught and I needed to comfort her.
"Oh, Chloe. No, it's not that. Come here," I said, reaching for her and pulling her slender body against mine. Even with heels she was several inches shorter than me as she pressed her head against my shoulder and fought back tears. "You have nothing to be sorry about. It's an awkward situation, but I understand...I do."
I was also feeling a wild mix of emotions at that moment. On the one hand I was trying to comfort a distraught woman who was feeling unsure and embarrassed by an awkward moment. On the other I was becoming aroused by the feel of this slender young lady as she pressed her body against mine in the dark seclusion of the parking lot. I placed one hand on her head and the other on her back as I felt her press herself against me. I suddenly became very aware of the awkwardness of the moment and knew we had to move to more private quarters if we were to continue this discussion.
"Look at me, Chloe." She looked at me with beautiful pleading eyes as I pondered our predicament.
"I am wildly tempted to take you up on your offer. But, I don't know, it just doesn't seem right. I mean..." Actually, I didn't know what I meant. I had never been in such a position before.
"Oh God, Jake. I'm so embarrassed. I can't believe I just said what I did. I'm so sorry!" She was practically in tears as I pulled her to me again to try and calm her down.
"Chloe, it's okay. Really. I'm flattered. I really am. I'm just...conflicted."
I hadn't exactly said no, because I couldn't. The temptation was overwhelming at this moment. I'd been her boss and she my intern. We'd had a professional relationship and there were certain lines that were not to be crossed.
But now I was facing one of those once-in-a-lifetime moments and I was reticent to pass on what could, potentially, be a wonderful night with a beautiful young lady. Since I was incapable of making a decision at that very moment, I pulled her to me and she turned her head and rested it on my chest.
And while my head may have been conflicted, my body was not. I comforted Chloe and she put her arms around me in a gentle hug, our bodies pressed together. As I gently caressed her hair, I felt my lower body responding to the closeness of this beautiful young lady. I became a bit embarrassed by the erection that was slowly growing between us. My first impulse was to pull away. But, I didn't, and as I hardened, I knew it became obvious to Chloe that I was getting aroused. Rather than push me away, however, she pressed harder against me. It was a clear sign that she knew I was excited and was responding in kind.
"Hmm. My mind is telling me no. But my body is having other thoughts," I whispered in her ear.
"Good," she whispered back. "I think this is one of those times when you should listen to your body."
And as we stood there next to her car in the back corner of the parking lot, we stared into one another's eyes, trying to come to some sort of agreement. My erection was pointed off to the side and getting in the way of making any sort of rational decision. And as we looked at one another for a few moments, our faces slowly moved closer to together and our lips met in the softest, gentlest kiss.
Her lips were like feathers and it felt like time stood still as we kissed. It was a soft innocent kiss for the first thirty seconds or so. Then I felt her tongue begin probing my mouth and I returned in kind. In a matter of moments we were locked in a deep French kiss. It felt like we had gone from zero to sixty in nothing flat. I leaned back, both of us panting and already out of breath.
"Okay," I said, our bodies now making it clear what was going to happen. Still, a clear head needed to prevail here before we were humping right there in a semi-public place. I took a deep breath and pulled back to disengage, my erection now a clear and unmistakable protuberance in my slacks.
"Listen, Chloe. Let's do this. Are you okay to drive?" She'd had two glasses of wine at the bar, but had switched to water once we were seated for dinner.
"Yes," she replied.
"Okay. Good. Why don't you drive me back to my hotel? We'll go up to my room and then we're going to talk a little bit and set some ground rules. I'm excited, obviously," I said, looking down at my erection straining my pants, "but I want to make sure we both go into this with a clear head. Sound like a plan?"
"Mmmm, okay, Jake. Let's go."
She opened her door as I went around to the passenger side and slid into the car. A few minutes later we were at the hotel and parked in an adjacent lot. It was only 9:30 so the night was young. She grabbed her shoulder bag and we entered the hotel, walking in like we were a couple staying there. No one paid us any mind and we were soon on the elevator. Chloe eyed me nervously, but I gave her a calm smile and a few reassuring words as we exited the elevator. We walked down the dim hallway in silence, both aware of what was soon to come.
As the door to my room closed we both stood for a moment looking at one another. She wandered over to the window, but the view of Lake Champlain was clouded in darkness. I turned a single bedside light on, took my jacket and shoes off, and used the bathroom, as did she. With that out of the way I sat on the edge of the bed and reached out my hands for her. She wandered over and stood before me. I placed my hands on her hips; she placed her hands on my shoulders.
"So, if we're going to do this, I need to make a few things clear. Okay?"
"Yes," she replied. "I'm listening." She looked so damned innocent at that moment. But I don't think I had ever wanted a woman more.
"First, if at any point in time you decide this is a bad idea or you want to stop, just say so. Okay? As much as I'm as excited about this as you are, I want to make sure you're comfortable. Deal?"
"Yes, deal."
"Second, I want you to promise that you'll be honest with Ken about this. Is he going to think it's weird that you decided to sleep with an older man who was your boss at one time?"
"I will. We promised to be honest about whatever experiences we had. He's told me, as hard as it was to hear. And I will do the same." She hesitated. I knew there was more. "And as far as you being older, well, I like that. It makes me feel safer. And it makes me excited knowing that you will be gentle and caring. That means so much to me. And also arouses me incredibly. I'm very attracted to you, Jake. I always have been."
"Well, that makes two of us, Chloe. I've always been incredibly attracted to you as well. You are a very beautiful woman and the thought of being with you. Well, you saw, or felt, my state earlier," I explained. She giggled.
"Yes, I did. It was a very impressive display," she joked.
I took her hands in mine as I sat and she stood. I was getting lost in her eyes and couldn't wait to touch her, explore her, and give her pleasure. But first I needed to make sure we were both on the same page.
"Finally, I want to ask you a few questions so I know what your previous experiences have been like with Ken - what you like or don't like. Okay?"
"Sure," she replied. "Fire away."
"Can I assume you both have enjoyed oral sex?" I expected an affirmative answer, but was a bit perplexed by her reply.
"Oh, yes. I love oral sex. I think I've gotten pretty good at it, if I do say myself. Ken certainly loves what I do to him."
I hesitated before probing a bit more. "That's good. But what about him? Does he go down on you?"
"Well, not really. He doesn't really like doing that. So...I guess the answer is...no."
I tried not to look dumbfounded, but I was.
"Really? My God, I'm amazed by that. I find giving a lover oral pleasure to be one of the biggest turn-ons I know of. A man should worship his lover's pussy."
"Well, I guess that's why we're here," she giggled. "You can do whatever you want, Jake. I'm here to learn." She smiled the most seductive smile. "And I'm just being honest," she added.
"Good. So, tell me what positions you like. How does Ken make you achieve orgasm?"
"Well, we've tried all the positions. I'm not sure I have a favorite, though I do like being on top sometimes," she suggested. "As far as orgasms, well, I'm not sure. I think I've had some, but I can't say for sure." She looked at me almost pleadingly. I was, once again, dumbfounded. Could it be that her lover of six years had never actually made her cum?
"Do you masturbate? Or ask Ken to try and please you when you're making love?" I was trying to make sense of an increasingly bizarre situation.
"Yes, I masturbate sometimes when Ken isn't around. When we have sex, he usually has an orgasm and then, well, he curls up and goes to sleep. What he does always feels good, so I don't complain. It's just, I don't know, that's the way it is." I looked at her with what had to be a quizzical expression on my face. "I'm happy," she added, not all that convincingly.
I let go of her hands and put my hands on her hips again. The hotel mattress was high so I was perched on the edge of the bed and our faces were even. Her warm curves felt good under my hands and she had an impressive flair to her hips for such a slender girl.
"Well, one final thing, Chloe. I'm not going to hold back. I'm going to make love to you..."
"Yesssss," she whimpered. "Please! I want you to do it. I want you to do everything."
"I'm going to fuck you , Chloe," I added for good measure.
"Oh, God. Yessss. Please, Jake," she gasped.
If I'd had any hesitations going in, they were gone now. This was going to be one incredible night.
It was time. I spread my hands on her slender back and pulled her to me slowly. Our lips met in the most tender, delicate kiss. The room was silent except for the tiny whimpers and soft moans from Chloe - and then me. And, just as in the parking lot, our kiss deepened quickly until our tongues were once again probing and exploring.
She was a good kisser; I had to give her that. And I have loved kissing since my earliest days of sexual awakening as a teenager in junior high. Her hands were on my shoulders and mine on her waist, as we focused on our lips and tongues and mouths. Once again, my erection had invited himself to the party and stood hard and proud between us. Chloe didn't seem to mind; in fact she was pressed firmly against it. We broke our kiss.
"Ready?" I asked, already knowing the answer.
"Mmhmm," she replied softly. "I am."
I sat back on the bed and spread my legs. I pulled her to me, still standing.
Her dress was sleeveless and buttoned down the front. While the bodice was snug against her lovely young breasts, the short skirt hung loosely around her smooth slender thighs. As I looked into her gorgeous eyes, I began to unbutton her dress - slowly - one button at a time. She looked at me expectantly as I did so.
As one button after another fell to the side, I unveiled a sexy black bra. I didn't look at it immediately. I just continued to look into her eyes as I continued undressing her - telling her with my gaze that I was going to unveil her tender body. I unbuttoned the front down to her waist and then put both hands on her bare tummy, feeling her catch her breath as I did. I continued to look her in the eyes as my palms slid up her bare skin until slowly coming to rest under her bra clad breasts.
Her bra was a very thin one, no padding. Her breasts felt surprisingly full as I palmed them through the lace of each cup. She gasped slightly as I fondled her flesh and felt her nipples protruding through her thin bra.
"Lovely, Chloe."
I would return to her breasts in short order. But suddenly the urge to slide my hands up her legs made me change course. As we continued to look at each other, my hands dropped to her knees and then began a slow ascent up the outside of her long smooth thighs. Her skin was just as soft as I expected and a little whimper escaped her mouth as my hands arrived at her hips and then slid around to the rear.
She was wearing a very tiny thong - the color yet to be determined - and as each hand cupped the soft generous flesh of her cheeks, I leaned in to place a kiss on her bare belly. She moaned as she put her hand on my head, encouraging me to continue.
"Yes," she cooed softly. "Please. More!"
I would return to explore that lovely ass later. But first, the dress had to go. I reached up and slid the top off her shoulders. It fell to the floor in a silken heap as I gazed at her standing before me in a black bra, a tiny black thong, and dark blue strappy heels. I don't think I had ever seen a more desirable woman. I'm not sure why, but black lingerie on a pale innocent looking woman has always been an incredible turn-on for me.
But she was still partially dressed and it was finally time to unveil her precious breasts. I could see the tips of her nipples poking slightly through the thin bra. I wanted to see them. I wanted to suck them. She saw me eyeing them and cupped them both seductively.
I reached behind and easily unclasped her sexy black brassiere. She held it in place for a few seconds - a moment of modesty that passed quickly. I gazed expectantly at her body and she looked down at me as she let the bra fall away and to the floor in a tiny black heap.
"Oh, Chloe. Your breasts..." I exclaimed. Words escaped me. Her pale white breasts were small, but beautifully shaped and tipped with the loveliest nipples I had ever gazed upon. They were small as well, but the nipple tip itself was darker than I expected and quite distended - a clear indication of her own arousal. Her breasts looked very delicate and extremely sensitive.
My hands slid up her tummy and cupped her from below, pushing her tit flesh upwards as I leaned in and gently licked her swollen tips. My tongue washed one, then the other, before I puckered and gently kissed each beautiful nipple. I sucked softly and listened as I heard her breathing catch and a moan escape from some deep dark place.
"Oh, Jake. Yesssss," she encouraged. "Suck my nipples. Oh my! Ohhhh..."
It was clear from the very start that this young lady's body was incredibly sensitive as I did my best to lick and kiss and suck her gorgeous nipples and massage her breasts. I pulled away and looked up into her hungry eyes. She watched as I licked the fingertips of each hand, and then lightly rubbed them over the glistening dark tips of her stiffened tips.
Her erratic breathing told me everything I needed to know. She was thoroughly enjoying the attention and I was loving giving it to her. She deserved to know how a good lover worships and treats the object of his desire, especially a lovely delicate pair of breasts.
I expanded my search as my hands glided all over her smooth body. Her skin was like silk and she continued to respond with ooh's and aah's as I explored her shoulders, arms, belly, back, legs and the impossibly sexy curvature of her glorious ass. This girl was gorgeous and even more beautiful in the flesh than I had expected. And her verbal and physical response to my gliding touch was a testament to just how sensitive she was.
I looked at her breasts, standing so proud and firm; the nipples pointing just slightly up, begging for more attention. As I looked at them, my hands circled behind once again and cupped the most perfect of bubble butts. My palms encased her cheek flesh, my fingers curled into her gap and I could feel the heat emanating from between her legs.
"Oh, Jake. I love the way you touch me, baby. That feels so good," she whispered.
"We're only getting started, Chloe," I said. "Only getting started," I repeated as I leaned in once more to French kiss each distended nipple. Then, I placed my hands on her curvy hips and turned her.
"Mmm. Let me see that back side, Chloe."
She turned demurely and I hissed under my breath as her perfect ass came into view. The tiny triangle of black satin sat just above the crack of her cheeks, disappearing down into the deep crevice between two of the most perfectly formed cheeks I had ever laid eyes on. I had admired this ass in a pair of tight jeans before. But I was still not prepared for the perfection that now presented itself to me. There was not a wrinkle, dimple or blemish on her flesh and the combination of the flare of her hips and curve outward of her derriere itself was an intoxicating sight. And now it was here before me for the taking.
I reached out with both hands. I touched. I squeezed and I fondled. I moaned my appreciation as my hands wandered up and down the length of her body from behind, always returning to the soft firm flesh of the most perfect ass I had ever had the privilege to touch.
"You are so incredibly gorgeous, Chloe. I mean, I knew, but..."
"Thank you, Jake. I'm glad you like it...that you like me."
I stood and pressed up behind her. I wrapped my arms around her and cupped her lovely breasts as I kissed her shoulders, nibbling my way up her neck to her ears.
"I can't believe we are here," I whispered. "This is a dream come true - a fantasy made real. I love touching you, Chloe."
"Mmm," she crooned. "It's nice to be so appreciated."
My hands began to slide down off her breasts and graze along her taut tummy. But before I slid far enough, she shifted positions on me.
"You have far too many clothes on, Mister. Time for that to change," she directed, as she took my place seated on the edge of the bed and turned me to face her. Her fingers began hurriedly unbuttoning my shirt, which she unceremoniously pulled out of my trousers. As it became loose I assisted in removing and flinging it off to the side. I had already taken off my shoes, so I removed my socks and was now down to my pants and underwear.
She immediately began to unbuckle my belt and there was an urgency to her actions that excited me. She wasn't being shy and demure anymore. She was no longer the innocent girl next door. She was bound and determined to have me undressed alongside her. That was fine with me.
Once I was unzipped she dropped to her knees - a move reminiscent of a porn clip, but done in a totally sincere manner. She grabbed the waistband of my pants and boxers together and pulled - down. The downward motion pulled my fully blown erection with it. And as she got to mid-thigh, my stiff cock sprung out with a ferocity that made her laugh as it bounced stiffly right in front of her face.
"Oh my God, Jake!" she exclaimed, as her eyes widened and she took in the hardness and length wavering right in front of her face. "It's so...big...and hard." She lifted it in her small hand, appearing to feel its weight and mass. I hadn't been this turned on in a very long time, and that, I knew, was evident even to her untrained eye. She circled her thumb and forefinger around the girth of my tip while her other hand reached up to cup the tight spherical mass of my scrotum. She looked up at me with hungry, lustful eyes and suddenly her innocent face seemed to reflect the dirtiest of desires.
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