I am Torn Between Bliss and Guilt

I have to get this off my chest: I did something and now I have mixed feelings. I feel both fantastic and guilty, but mostly I feel a bit perverted. Let me tell you what happened this weekend.

I belong to a group of women who meet once a month to wine, dine, chat, and in general have a good time. This past Saturday we met for dinner at one of our member's homes. Her son was spending the weekend there with a college friend and they were milling about, mooching the food and wine. Well, at some point the son's friend walked up to me and started a conversation. He was flirty and a little cocky and was carrying on about working out when he mentioned something about wanting me to be his personal trainer. Cindy, one of the women in the group, actually happened to be a personal trainer, and as I am a bit on the fluffy side and not athletically inclined, I figured he had me confused and was referring to her. When I said so, he looked at me confidently and simply replied "No, I'm not confused, I would want YOU to train me." He looked intensely into my eyes for few seconds and moved on leaving me flattered, but shaken. A few moments later he deliberately looked at me after he used the word MILF during a conversation with his friends.

Hmmmm?

He really WAS hitting on me!


I became flustered, looked around, this kid was in a group of middle-aged women, friends of his buddy's mother, and he was openly hitting on me. He was good looking: cute AND ripped. I could not quite understand; there must have been dozens of girls his age that would have killed to go out with him.
 A little bit later, he walked up to me and said "Think about it," then turned and went back to his friend.


It was quite an ego boost. For the rest of the evening I only saw him from afar, but when I got home, I realized that I was really aroused by the conversation.

But it was casual, and there was nothing I was going to do about it, so I let it go. I had almost forgotten about it by morning. Then, about noon I received a text from an unknown number. I was startled when I read the words:


"Did you think about it?"


I was not expecting this. He'd been serious.

Completely off guard, I went to my husband, to whom I had not mentioned what had happened and laid it all out.
 He smiled and said

"Do you want to do this? Because if you do, I can go to town to run some errands, and give you some privacy."


I bit my lip, my brain said "This is crazy," while the throbbing between my thighs said "Obviously you want this."


"Yes I do!"

Kissing me on the lips, my husband said

"Well, have fun, and please share with me the details later."


I texted him back, and gave him our address, to which he replied:

"I'll be there in 45 minutes."


And there I was, not sure what was more swollen, my ego or my pussy.


Now for the details... I was bent on setting the scene. I ran to the kitchen, sliced some cheese and fruit, washed a bunch of grapes and opened a bottle of white wine. I considered champagne, but sometimes it gives me a headache and that is something I did not need.


I poured myself a glass to calm the flutters in my belly. That felt weird. Hell, this was probably an inexperienced college kid, why was I nervous?

I took everything to the deck, because the weather was ideal for what I had in mind. I checked the temperature on the hot tub and it was perfect. I set up a small table with the wine, cheese, and fruit.

I carefully positioned two chairs about three feet apart with a small table to one side, I actually picked a taller chair for myself and a lower one for him. I wanted him to have the visual vantage point.

I ran to the shower, carefully soaped myself with a nice almond soap, rinsed off, and then did it again, rubbing a few very sensitive erogenous points along the way. I used the almond soap because it leaves a nice scent and I was worried that the perfume I usually apply to my neck and inner thighs might be a bit much this early. I dried, brushed, looked down, checked my bush and considered some trimming. Kids his age are unaccustomed to pubic hair.

I turned to Paul as he was ready to leave and asked him, "Should I trim?"

He gently pushed me back on the bed and spread my thighs.

"Let him see what a real woman looks like." He ran the tip of his finger between my lips and whispered "Annabelle, you're already wet," He kissed me softly and left.

I picked a pretty set from my lingerie drawer, thought about what dress should I wear and then on second thought chose a very sexy silk kimono robe.

I did a twirl, thought about it, decided to be naughty, and took the bra and panties off.

Before long I received his text.

"I'm here."

I took a deep breath and sent back:

"Come around the back. I am in the garden." I sat in my chair and waited for him, my heart pounding, and my inner thighs throbbing in anticipation.

He walked around the corner of the house, looking rather flustered. He had made an effort to dress up, and I liked that. He had a pair of khakis and a Polo shirt that nicely contoured his broad chest and pecs.

I stood, gave him a peck, looking straight into his eyes, and motioned him to the chair. I turned my back, knowing that the gown was clingy, and asked,

"Are you actually old enough to drink?"

"Yes ma'am, I'm 23," which was probably a lie but I knew he was of legal age. The "ma'am" part did make me cringe, though.

"Call me Anabelle", I muttered, "under the circumstances".

His hand shook slightly as I handed him his wine glass. I knew I'd need to settle him down a little or things would never work out. I said "So... Great timing, I have the afternoon free, as my husband is out of town", well-knowing that he was probably not far waiting for my "come back home" call.

Teasing him, I asked "Tell me this about being a MILF, what do you mean by that?"

He blushed and mumbled something about that being the way that guys his age referred to attractive older women.

Noticing his embarrassment, I leaned forward and smiled, I reached up to touch his face and said "It's okay. I'm flattered."

I was enjoying toying with him. I uncrossed, then re-crossed my legs, making sure the gown slipped a bit and gave him a good look at my thighs, exposing the pale skin in contrast to the black silky robe.

He tried to keep his eyes focused on my face but they kept wandering down, I looked at him intently, took a sip of my wine, slipped the other hand under the robe, cupping my breast and said

"So, you found me attractive. Tell me more. What do you like about me, I certainly don't look like your college friends." I let the robe fall a bit more, exposing some breast, belly and thigh.

His expression changed and he became quiet. He looked uneasy, eyes darting over my body.

I decided to throw all caution to the wind.

"I know why you are here and that is why I invited you."

I turned to face him letting the gown fall open completely.

"Stand up and come here," and when he did, I pulled him by the belt, wrapped my hand around his neck and began to kiss him.

He began to probe clumsily, so I said "Wait, you asked me to train you, and I will." I began to kiss his face, to gently nibble his lips and then probe him with my tongue, slowly, gently.

I pulled back and said, "Now it's your turn" and he began to kiss me in a similar manner.

Fast learner.

"I will train you to love and please me the way I like it."

I stood and said: "Take off my robe." Trembling he slipped it off my shoulders. Finding that I was totally naked left him breathless.

I began to unbutton his shirt, and he tried to help me.

"No! I want to do this," I said, and then proceeded to untying his shoes and unbuckling his belt. As I did I brushed my hand across the front of his khakis and I could feel him hardening, very much so!

I took my time and soon was on my knees with my fingers inside the elastic of his shorts, waiting till I could see the effect I had on him, letting him feel the warmth of my breath on his inner thighs, waiting to see what was in store for me. I was not disappointed. As I peeled down his shorts, a beautiful cock sprung up, curving towards his bellybutton as only youth allows.

I had planned to seduce him in the hot tub, but I was too far gone. I wanted him now. I took him by the hand and, tugging gently, said "come with me!"

He followed me obediently as we headed towards my bedroom.

I had left all the blinds up, the ambiance lights on, the large dressing mirror at the foot of my bed strategically oriented and my music tuned to my favorite sex playlist.

I laid down, still holding his hard cock in my hand, and told him:

"I want you to look at me. Take a very good look at me, and I will teach you how to please a woman."

The look on his face was priceless as his eyes roamed over my body,

By this time, I was flushed, the skin on my chest blotchy, my nipples erect. I was hoping he could read the signs of arousal, because aroused I was.

His gaze kept on wandering towards my bush, so I asked: "You haven't seen a woman with hair, have you?"

"Never." He croaked, He was barely able to get the word out.

"Come here. Kneel there," I said, motioning towards the foot of the bed.

And when he was very close, I said, "Look at me, this is what we're going to share," as I spread my thighs and gave him his first glimpse of a natural pussy. I knew I was sopping wet, I knew I was swollen, I knew I was ready, and I was going to milk this.

"Do you like what you see? Do you want to feel me, taste me?"

The look on his face said it all, but I was going to make him wait.

He was tall, about as tall as my husband. He was muscular, not the bodybuilder type, but muscular still. He was almost hairless compared to my Paul. He had rugged features, but an almost innocent demeanor.

I knelt on the bed and began to kiss his face again, working down his neck, his chest, his nipples. I felt them harden; he shuddered as I nibbled on them. I continued to explore his body with my lips and the tip of my tongue: his hard abdomen, his ripped six pack, I deliberately kept my hands away from him, letting him concentrate on feeling my mouth over his body. I kept moving down further. As I reached his groin, I felt his balls ripple. I ran the tip of my tongue along his cock till I felt a small pool of juices collecting at the tip. I nibbled my way down, then took his cock in my mouth. I saw, mesmerized, that he was quite thick, quite large. The veins on his cock looked like a vine running towards his cockhead and a nice plum-like head with a pool of precum awaited me.

I licked, I sucked, I tasted him. I kept my hand behind his balls gauging his reactions, ready to halt at any threat of him cumming before I had had my fill.

Yes, this was for my enjoyment as much as his.

I licked his scrotum, worked my way up his shaft. Too soon I had him moaning, at times almost whimpering.,

When I said.

"You want me now?"

He scrambled up, his cock hard as a rock, I rolled him on his back and straddled him.

"I want you to see what you will be getting." I told him as I moved over his face. "You are going to learn how to please a woman," and I knelt above him.

"Spread my lips" I ordered,

I knew I was swollen, wet, pulsating. I wanted him to get a good look at my clitoris, which felt like it was about to explode.

He eagerly complied. He was actually quite gifted, and I soon found myself telling him "Now, taste me, lick me." He began tentatively but soon became quite enthusiastic. He seemed to read me and follow my cues and before long he had me shaking. I exploded in a terrific orgasm, feeding him some pent-up juices.

When i recovered my breath, I kissed his lips, tasting myself on them. "You're good," I told him, and I straddled him, moving my hips above his cock.

It was my turn to impress him. I placed a pillow under his head so he could watch, listen, smell and feel what was about to transpire. I began by rubbing him between my lips, then taking the tip of his cock at my entrance, moving, squeezing, milking, then looking at his face as I slowly but inexorably took him in.

When I was fully impaled, I had to stop and adjust; this kid was big, I felt him up to my bellybutton.

I remained motionless, allowing my vaginal muscles to work on him. The effect of all the Kegels I have done in my life... His expression was priceless! I was milking him for what he was worth and I began to feel the build-up.

I knew he was not going to last much longer... at least this first time. We were both too worked up, so I began to slide fully, to travel the entire length of his cock, I would pause when the tip reached my entrance and then plunge down on him, feeling him bottom out. My pussy was so wet it was making all kind of noises as we both took in the sounds and smell of fucking.

I rotated, I tried every angle till I found what seemed to please him the most and then concentrated.

It was lovely, he began to shake, he grasped me so firmly, he tried to control himself and that made me more relentless. I churned till he tightened, then he lifted his pelvis, and tried to reach the deepest corner of me. I felt him moan, his cock jumped inside my pussy, he shook his head, let out a scream and came., I felt his cum rushing up his cock, splashing, filling me. We finally collapsed in a heap, catching our breaths, with my ego soaring as he kept on saying,

"This is amazing, this is amazing, I never knew it could feel this good, my God I never knew."

I had done my good deed for the day, and had done my pay it forward.

But I was far from done with him, although that part of the story is best left for another day.