The Debauching of Emily Ch. 01

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Divorcee expands her sexual horizons.
3.6k words
4.51
25.1k
2

Part 1 of the 3 part series

Updated 09/22/2022
Created 02/05/2011
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Emily was divorced. This clearly was her first attempt at dating. She didn't talk about her divorce or her loneliness. Those were subjects she just avoided. She was so ashamed of the divorce that she wished she avoided the subject of marriage/divorce completely.

We met through mutual acquaintances. They weren't even friends. I barely knew Ted from the Rotary Club and Emily worked with Gladys but wasn't close to her. To this day I can't imagine why we met. But, we did.

I called her on Ted's urging. She answered the phone and was clearly busy. I had called at the wrong time. More than a few awkward pauses and interruptions, we finally got into the swing of things and began to have a normal conversation. We agreed to lunch ("What's the harm in that?").

The first time she arrived in a very conservative dress that ended at her knee. Not very revealing but I saw through it. She was pretty. I looked below the knee and saw a calf that was fit and muscular. She didn't have a fat ass and her sleeveless sweater showed arms that had a subtle line of muscle: Just right. Her pretty brown hair ended just at her shoulders. Shorter than I preferred then. It smelled wonderfully.

Several more lunches and soon I realized that I thoroughly enjoyed her company. She knew enough about sports and I knew enough about Shakespeare that we could spend time together without driving each other crazy. On one of the lunches she wore a tight top under her conservative business coat. I got just enough of a peek at her sweater kittens to know that I REALLY NEEDED to know what was under those clothes!

Finally she agreed to a date. A REAL date not just lunch. I went to her house to pick her up. Up to that point she'd only seen me in my truck. That was the most practical way of getting into town. I always stopped off at the hardware store on the way home. For our date I got the Corvette detailed. It looked fast. It was ready to impress.

I arrived at her house just on time. When I rang the door bell she was ready and had her coat already on. I couldn't tell what she was wearing but she had some nice, high-healed shoes and dark hose that were almost fishnets.

"Oh, you have a sports car," she said as we walked to the car. She seemed surprised and not too pleased about getting into a car that was six inches off the ground in her dress. How she was going to get out concerned her even more.

I decided to go someplace special and splurged on a new, French restaurant down town. We made pleasant but uncomfortable small talk at first. As we entered the freeway the rush hour traffic became the Friday-night-going-out traffic. The onramp descended down onto the highway in a straight line. As we approached the road I saw a space well in front of us. A quick check of the side mirror and it became obvious that the only way into traffic was to step on it ('stomp' on it was more like it). The 330 horses came to immediate life. The car couldn't WAIT to go faster. Out of the corner of my eye I saw Emily's head snap back as the g's pushed us against our seats. She let out a surprised squeal and then happy laughter like she was on an exciting amusement ride.

"Sometimes going faster is the best thing to do," I blurted out trying to excuse my aggressive driving.

"Hmmm. I agree," she purred.

I wasn't sure what to make of that so I awkwardly changed the subject and moved on in the conversation. The traffic lights conspired against us. We hit every red light between the freeway and the restaurant. She didn't seem to mind and we chatted about her job in the insurance industry. It's hard to believe that line of work would be interesting but she spoke as if she enjoyed it. She had made good friends there and they supported her through the tough times.

We arrived at the restaurant and the hostess offered to take her coat. I was looking out into the restaurant at the time and didn't notice her slip out of her coat. When I glanced back I did a gigantic double-take and flashed a quick, nervous smile to try to hide my amazement. Emily caught it and gave me a sly look in return.

She gave up on dressing conservatively that night. She had a black cocktail dress on that showed a good amount of cleavage. The dress ended well above her knee showing off her gorgeous legs. Her hair ended just at the base of her lovely neck. I couldn't help but think it would be nice to dine on the nape of that neck.

When she was standing next to me I couldn't help but look down the front of her dress. Her breasts were clearly very large, very real, and quite spectacular. We stood there for several minutes and it wasn't lost on me that everyone in the room was looking at Emily (and wondering what the hell she was doing with me).

We were seated and continued chatting. I had to force myself to avoid looking at her tits. It was all I could do to keep from clearing the table by pushing everything off with both arms and doing her right then and there!

We laughed a lot and things took a turn from good to better when she offered to feed me some of her dessert. I happily accepted a piece of her chocolate cake and we giggled. I realized the wine was starting to go to her head when she leaned forward to speak in conspiratorial tones to me.

"Do you like my dress," Emily asked with a slightly tipsy slur.

"I think you make that dress look beautiful," I replied. I thought I was clever.

"I bought this low-cut cocktail dress just for you. I'm surprised that I haven't caught you looking down my cleavage once tonight."

"All I've thought all night was 'Look in her eyes. Look in her eyes,'" I pleaded helplessly.

She smiled for a moment then said, "You can look if you'd like."

I eyed Emily up carefully concerned that I might be falling into a trap. Finally I let my eyes drop to the top of her sexy garment.

"Mmm," I said, "I bet it's just heaven in there."

Her eyes got large and she reached out to pet my face and in an exaggerated way said, "Check, please!" We laughed. I made sure the waiter did not pass us without knowing that I wanted the check.

As we departed she took my arm. We made our way to the gardens surrounding the building and enjoyed the cool, crisp evening air. Just as we reached the ornate fountain I decided to make my move. I wheeled her around and slipped my other arm around her waist. Apparently she had the same plan because she was ready for my advance.

Like two soldiers ready for battle our lips met and engaged in a fierce struggle. Damn, they were soft. Her kisses overwhelmed me and I let my guard down. Her initial attack was quickly followed by a tongue that slipped between my lips. There was no stopping her. We squeezed each other as if in synchronized death grips. Finally after breaking free and looking furtively around to see if we had any gawkers, I suggested, "Let's get you home."

Realizing what I really meant, she just nodded her head and grabbed my hand.

This time the traffic lights were on our side. As if willing us toward hot, monkey love, they turned green just as my car approached them. Emily told me later that the Corvette's throaty growl gave her just the right vibrations. Soon we were in front of her house. I parallel parked and turned off the car.

"Well. Here we are," she said matter-of-factly.

"Here we are," I countered nonchalantly.

"It seems awfully early." More matter-of-fact chat.

"Yes it does." Long pause.

The we both started together: "Perhaps we could." "Oh. You first."

More awkward pauses then she said, "You're welcome to come in for a nightcap if you'd like."

"I'd like that," I said, comfortably.

I got out, walked around and opened her door. She waited for me and let me help he out. We silently walked to her door at a comfortable pace arm-in-arm. She opened her door and heard the horn of my car honk signaling to the neighborhood that I wouldn't be coming back to it this evening.

Once inside she offered beer or wine. "Just water, please," I said.

"Water?"

"Yeah, I'm thirsty. A cold glass of water would be just right."

She poured two glasses of water and joined me on the couch.

"Water for you too?"

"You got me wanting some water."

"You're gonna need that water when I'm through with you," I thought.

We enjoyed a few sips and I put my glass down. Then I put hers on the coffee table as well and turned toward her. She didn't need convincing and we were back at letting our tongues do the talking. This time it was even more passionate with her hand running through my hair. She tasted like mint. This is a woman who plans ahead.

I needed more than just kisses and told her to lay back in my arms. She obeyed. I didn't want to rush it but I just had to get my hands on those tits! Soon I slid my hand up and gently brushed against her left breast trying to test the waters. Apparently this felt good because she moaned ever so slightly. This led to firmer caresses and more moans.

"Let's go to bed," I whispered in her ear. She looked at me startled. It was a pause that seemed to last a long, long while. Finally she nodded silently almost looking like a women condemned to die. I wasn't sure what to make of it but quickly ignored it only thinking about her sweet ass.

She held my hand as we walked upstairs. We reached her bedroom and there was already a side light on. That was all the light we needed. The dress unzipped smoothly and I pulled the sleeves over her shoulders. She shifted her weight backward and lowered her arms. The dress dropped to the floor leaving her in a lacy bra, thigh-high hose and matching silk panties.

She fumbled for my shirt buttons. Why is it so much easier to get a woman naked than it is a man? I should have at least unbuttoned my shirt sleeves on my way up the steps. More pulling, tugging and unbuttoning then I, too, was naked.

She paused for a moment and looked right into my eyes.

"What's wrong?" I asked.

"I, uh, I don't have much experience with this sort of thing." She stumbled over the words.

"Ah. Here it comes," I thought. "I'm not gettin' laid tonight. She's probably gonna start crying now. I've seen how this movie ends and it ain't exactly rated X!"

She said she didn't have much experience even before she got married. The last two years of her marriage were without any sex and it had been two years since her divorce.

"Wow. That's a long time."

"Yeah. I guess it is," she mumbled.

To assure her and to get into her naked body as soon as possible I opted for a time-worn cliche.

"Don't worry," I said, barely paying attention and kissing her neck. "It's like riding a bicycle." Then absentmindedly added, "Only without the seat on."

It took a moment. She was highly distracted by the nerve-racking first attempt at sex but then the comment sunk in. "Without the SEAT ON," she realized.

She burst out laughing. She completely lost control and an initial giggle disintegrated into a full-out belly laugh. Her muscles tightened up so much that there was no way I could enter her in this state.

After realizing the effect of the off-hand comment, I started to laugh too. Before long we were holding each other with our faces buried in each other's shoulders and enjoying the moment. I used the distraction to unhook her bra.

Soon she settled down and stopped laughing. Emily looked at me with a curious, bedroom eyes sort of look. Then while still looking straight into my eyes she eased backward allowing her bra to fall free. I broke from her gaze and moved my hands up to her amazing breasts. She closed her eyes and leaned back.

He bed was a large, ornate victorian four-poster bed. I moved her around and helped her up, onto the mattress. She laid back and allowed me to slide her panties off.

Now this beautiful woman with large, firm breasts lay before me. I slid my hands up her incredibly soft thighs and further up her body to her breasts. I climbed on top of her kissing her deeply. I supported myself with one arm and reached up to continue massaging her breasts with the other hand. After several kisses I slid down and began to kiss her breasts. She arched her back enjoying the attention.

I continued down to her navel and began to tongue it while massaging her breasts and lightly squeezing her nipples.

"Mmm. She's got an 'outty'. That's good eatin'," I thought.

By now her nipples were huge and hard as rocks. They looked like large rubies on the tips of her breasts. I continued this for some time and she began to moan more frequently.

"Ah. Ahh yes. Yesss."

I started lower. She grabbed my head and said, "No. You don't have to do that."

"I want to," and began sliding my hand over her well-trimmed bush.

I slid down and began kissing the inside of her thighs. She cooed nervously. I began blowing on her pussy lips. By now her labia was enflamed and ready to give her wonderful pleasure. More nervous groans. I ran my index and middle fingers over her lips, parted them and plunged my tongue onto her clit.

She moaned loudly this time and arched her back even more. I continued licking and slid two fingers into her wet pussy feeling for her g-spot. By now she was grinding her hips and pushing my face firmly into her. I kept at it and noticed that she started to quiver. More g-spot action and clitoris licking and then she lost control. I wasn't sure what to do but figured I'd keep going until told to do otherwise. She was yelling like she was at a concert. Her hips were moving up and down and she was breathing like she'd just run a marathon.

Soon she was pulling my head up and yelling, "Stopstopstopstop."

"Oh God! Ahhhh!" panting furiously. "That was amazing. Uggh! I'm still sensitive down there."

I let her catch her breath as I slowly slid on top of her. She wrapped her wonderful arms around me and pulled me close. I waited a moment more then maneuvered my raging penis.

I used one hand to line up my cock and once the tip was in moved my hand around her shoulder. I smoothly slid my cock deep inside her. Emily let out a loud, surprised gasped. I pushed it all the way in quickly and held it there. She stared at the ceiling in shock. After hearing her panting for several moments she looked at me and softly whispered, "Yes. Yes."

I slowly withdrew my hard dick and gently slid it back. She instinctively arched her back and grabbed my shoulders trying to steady her heaving body. A few more ins and outs and she began to lose control again.

It had been a few days since I'd had sex and my balls were full. Each thrust felt better and better. I knew I wasn't going to last very long and began to pump wildly. By now she was in her own world and began shrieking, moaning, and yelling, "Oh god! Oh God! OH GOD!!"

Then I felt the familiar tickle deep in my balls, thrust once more and held it there. The grunts from deep in my throat and her uncontrolled moans marked my exploding semen deep in her wet pussy. I pulled back and thrust in several more times with each shot of ejaculate. The wonderful exhaustion that we all enjoy at the end of some nut-busting sex swept over me and I collapsed on top of her. I dozed for a bit then came to. She had a satisfied, happy look on her face and moved her legs down in what was obvious pain.

"Haven't had my legs up like that in a while! It kinda hurts when I put them back together," she said laughing.

She got up and went into the bathroom. I figured I'd give her some time to herself and before long she emerged with a washcloth. It was well soaked in hot water and she used it to clean my spent cock and the cum that had shot out of her pussy onto my thighs.

"There, that's better isn't it?" she said in a relaxed, comfortable tone. After she returned she climbed into bed and laid her pretty head on my waiting shoulder. We rested silently. I gently stroked the base of her back and her tight ass. After a bit she raised her head and put her chin on my chest.

"Wooowww. That was pretty amazing."

"Yeah. I gotta say that really pushed me over the edge."

She put her head down again and began to run her fingers through my chest hair.

"I like your chest hair," she said in a far-off way. "Sooo sofftt."

I continued to caress that amazing ass while she enjoyed my chest. It felt really good.

She looked up at me again and said, "Like I said, I don't have much experience with, you know, this stuff...sex. I wish I had a better idea of what to do and how to please you. I like pleasing you."

"There's no substitute for enthusiasm."

"Mmm hahahaha." The hum of her agreement melted into light laughter when she realized what I meant.

"Was I enthusiastic enough for you?"

"Absolutely."

"Good. I want to make you happy. I want to learn more. What do you like?"

"I like having my balls caressed."

"Really?!"

"Love it." I took her had from my chest and slowly guided it down to my slightly emptier balls.

"Mmm hahahaha," she laughed and began to slowly and gently massage them. "Does that feel good?"

"Hell yeah."

"Good. Now I know. You like your balls massaged."

She continued caressing me and I continued caressing her. It didn't take long before I started getting erect again.

"Wooo!" she exclaimed. "What's going on here!?!"

"That's what happens when you massage my balls."

More giggles from her and then she slid down so she was even with my half-hard dick.

"Mmm. It was a good boy tonight!"

With that Emily started to kiss the underside of my head with short soft pecks. When she saw the positive effect and continued down the shaft until she reached my scrotum.

"So you like your balls massaged. Do you like them licked?"

And with that she began to lick one side then the other. I lost it and arched my back.

"Huh. You seem to enjoy this," she teased.

"Hell yeah!"

She dove back in enjoying the two things that had just given her so much pleasure.

"Yeah, stroke my cock while you lick them," I advised. Her hands were unbelievably soft and that just made my dick that much harder.

Soon she gave up on my balls and worked her way up my dick planting little kisses. I watched as she tasted the goo oozing from the top of my schlong. She paused for a moment and seemed to like what she tasted. After a brief moment Emily down on to my raging hard-on.

Up and down and up and down. FUCK! It was AWESOME.

"Do you like it?" she asked innocently.

"Hell yeah!"

"Am I doing it right?"

"Hell yeah!" I gasped. "Just treat you mouth like it's your pussy."

"Oh! Ok!"

With that she proceeded to suck and lick in a way that I'd NEVER experienced before in my LIFE! The desired result started to happen. I warned her then warned again. Just before I was about to explode, she used her amazingly soft hands to stroke my cock. She pulled back a few inches to watch the fireworks.

Although I had earlier pumped most of what I had into her underused pussy, I still had enough to create quite a geyser. The look of surprise on her face was priceless. She giggled and cooed and enjoyed every burst. After the festivities ended she slipped down for one last suck then raised up with a bitter look on her face. She thought for a moment and said, "Well, that's not so bad." Then proceeded to continue gobbling up the rest of my man chowder.

I was amazed.

She resumed her position resting her head on my shoulder.

"How was that? Did I do good?"

"Hell yeah!"

"Not bad for my first time, huh?"

"Oh! Don't give me that!" I protested.

"No, it's true! I never tried... before." she hesitated. I decided not to press it.

I didn't even care. If that was her first attempt, her one hundredth attempt is going to be pretty out of control. I didn't give a rats-ass if she gave other guys blow jobs. All that mattered was that she give me more of them!

"What did you think?" I asked.

"Hhmm. I LIKED it!"

"You were quite good at it."

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