Helen in High Heels Part IV [MF] [Long]

I transferred out.

It wasn’t all about Helen. I just realized that I didn’t really like my school. Besides Helen, I had made no other friends. The big city college style wasn’t working out for me. So I transferred out. I did my last two years in a small all boys college in a suburban town near the city. It was great. Small class sizes, knew my professors. It was very reminiscent of high school. It was a setting I was comfortable with, and I thrived. I did well in classes. I made friends. I even dated a couple of girls from the nearby girls college. It went great.

When I graduated, I went job hunting and found a mid-level job in my field but it was 3 states away. In July, I packed everything in my car and drove over.

It took me a while to get settled in my new setting and my new job. But by November, I was familiar and somewhat comfortable. It was honestly getting the hang of being an adult. I even asked a girl out on a date from the office, Jenna.

Christmas came around and I was thinking of not going back home to see my parents. I wanted to be an independent adult. But I also had some cash now I wanted to go home and flaunt how much of a big shot I was. Maybe even rub it into my older brother’s nose who was still living at home and working in landscaping (as I said, he was an asshole).

So I booked a flight. When I landed, my mom came to pick me up. This was unusual. She wasn’t the drive-to-the-airport-in-the-city-and-pick-you-up kind of mom. She was the wait-for-you-at-home-with-a-warm-meal kind of mom.

After the warm welcome, she said, “We have to pick up your dad.”

“Where is he?”

“The hospital visiting Jack.”

“Jack who?”

“Jack Whalen” I remembered. “He is sick again. His heart is giving out. Your dad told him he ought to lose weight and start working out but he never listened.”

“He never was a great listener.” I couldn’t help but comment.

We arrived in the hospital parking lot. My mom called my dad and told him we were here but he asked her to come up and see Jack and Helen. She hung up and asked to come with her. I didn’t want to. She asked again. I really didn’t want to. It wasn’t that I had any feelings left for Helen. It was a silly crush, I knew that. I just didn’t want to see her for some reason. Then I thought “I am a man now. I can go and show that off to her. I can walk in, stand tall and show her that I don’t care about her. She might have gotten an erection out of me when I was a young dumbass who was captivated by an older woman who showed some skin and a two-piece bathing suit on a hanger. But now I am an adult. I have a job. I make money and more importantly, I more experienced sexually. I can show her how far I have come.”

I walked up to the hospital wing Jack was in. Helen was in a waiting room. When my mom and I walked, she looked genuinely surprised. She hadn’t expected me. She quickly recovered her surprise and welcomed me with open arms. I tried to act aloof about seeing her and feigned concern about Jack, “How is Jack?” I said with concerned face.

“He is ok for now. The doctors say the next few hours are crucial in determining if he will make it or not.” She paused. “I honestly don’t know what I am gonna do without him.” She looked down.

“Don’t say that Helen. He will be ok.” My mom patted her on the back.

“Thank you folks for coming. It really means a lot to me. And I am sure for Jack too.”

We stayed for a few minutes and eventually got up to leave. We were told they were “turning” Jack and that we couldn’t see him. I was relieved. For someone who wanted to go to medical school, I didn’t realize how much I don’t like sick people. We got in the car and drove home.

When I got home we had dinner as a family and it was great. It was awesome seeing my parents, my sister, and even my jackass brother. He hadn’t changed. After dinner, we hung out more then eventually we all went to bed.

My room was kept in perfect shape, clean, yet everything in the exact place I left it. I lay in my high school bed. The same bed I had lain, thought about Helen and jerked off all those years ago and I couldn’t help but think about her again.

She had aged. That was for sure. I hadn’t seen her in 3 years at that point. But she hadn’t looked worse. If anything she looked better. When I saw her, she had been waiting at the bedside of her sick husband, about to be widowed and she still looked perfectly pristine. Her hair was perfect, outfit was elegant and most importantly of all, high heeled boots.

At that time, Jenna sent me a text to check on me. We started flirting until we both fell asleep.

Christmas came and went and we were all told to “Pray for Jack” again. He had pulled through the initial phase of recovery but the road ahead wasn’t an easy one. He apparently needed a liver transplant and he wouldn’t qualify it because he was older or had a bad heart or something. I didn’t care.

On December 28th, I had planned to take my sister out to her favorite restaurant. She had gotten all A’s in her first semester of college and I wanted to encourage her. As we were out, I got a text:

“I know its not Monday but how do you feel about meeting up for coffee?”

My heart sank. It was Helen. I had deleted her number from my phone but I couldn’t delete it from my memory.

My sister noticed. “Would you stop texting all your girlfriends and pay attention to ordering.” I was frazzled. I ordered, ate and paid, all without responding. I didn’t know what to say.

I didn’t want to meet her. What could she possibly have to say that I care about? I moved on to bigger and better things while she was stuck was the jackass. I started typing, not knowing exactly what I was going to say, “Hi Helen, it’s been a while for sure. I am glad to hear Jack is doing better and it was really nice seeing you the other day. I am flying out in a couple of days and I don’t think I will be able to meet up. I am sorry but I really hope Jack is ok. Praying for him. Merry Christmas and a Happy New Year.” My thumb moved to “send” but never pressed. Instead “Backspace”…

“Hi Helen, it’s been a while for sure. I am glad to hear Jack is doing better and it was really nice seeing you the other day. I am flying out in a couple of days but if you have time I could probably meat up with you today in the afternoon.” Send.

“Well, if we are meeting in the afternoon coffee won’t do or else I won’t sleep all night. How about the restaurant in the Wyndham? They have a great duck breast.”

“Sure, 4 sound ok?”

“Let’s make it 6. I still have to pick up some stuff before I get home.”

“Thumbs up Emoji”

​

I thought for hours what this meeting was going to be about. I genuinely had no idea. What could she possibly want? I wore the best shirt I had brought with me and I went to meet her. I took an Uber to the Wyndham.

I got there early. But I wanted to arrive late. I didn’t want her to think I was eager to see her. I wasn’t. So I circled the block twice. This only made me arrive 5 mins early instead of 25. I got bored walking and just wanted to get it over with so I walked in. She wasn’t there yet so I figured I only just wasted time walking around. She had a table reserved in the restaurant. “Whalen table for two” that felt weird. I sat at the table and got a glass of wine. Fifteen minutes later she arrived. I didn’t realize it then but she really had perfected the art of being fashionably late. She was only 10 mins late, just late enough to make you feel like a priority but not her top priority. You can’t get mad over 10 mins. As for fashionable, that was her MO. She wore a slender black dress with beige polka dots. The neckline was high enough to just to show the very top of her ample cleavage, only the very top, but low enough to highlight the elegant pearl necklace, real pearls I am sure. I had my back to the door so I didn’t see her walk in at first but the click clack of her heels on the hard wood floor of the restaurant is what made me turn around to see her. Of course she wore heels, somethings change, that wasn’t one of them. And who wore open toed shoes in December??? The shoes were beige and they matched the polka dots on the dress and the clutch she had in her hand. Definitely fashionable.

She walked over, I stood up. We kissed on the cheeks and sat down and exchange pleasantries.

The restaurant was upscale. It was more than I could afford, or rather, more than what I should pay for. The cheapest plate was $40. Helen wasn’t a cheap date, that I knew. It occurred to me that with Jack’s overwhelming wealth, she had probably long forgotten, or could have never guessed, how much a person with an entry level job makes. I figured I was gonna get cleaned out anyway so I thought, might as well order whatever I want.

After getting through the pleasantries Helen asked, “So how are you doing? Really? We have a lot to catch up on.”

“I am good. I am working as a software developer for a networking company now. It’s a good job and there is opportunity to move up in the company. Besides, cost of living in Raleigh is pretty cheap anyway so your buck goes a long way. How are you?”

“I am well too. You know what’s going on with Jack. The kids are well and in boarding school now.”

Her answer was short. She didn’t want to talk to much. The silence got awkward.

I got a text. I reached for my phone. It was Jenna. I looked up and she was watching me look at my phone. It hadn’t occurred to me that it was rude to look at my phone. I put it down.

“Are you coming to church on New Year’s Day?”

It was small talk, and I suddenly grew impatient. “Maybe, we will see… So, we are here, what did you want to talk about?”

She was taken by surprise by my forward question. She had been acting different. The Helen I remember asked poignant questions and drove the conversation to where she wanted it to go. She always knew how to get me to talk about exactly what she wanted me to talk to her about. It wasn’t manipulation through conversation as much as it was always stimulating to tell her what she was asking about just to see how she reacts and what she thinks of my answer. She had made me want to tell her exactly what she wanted to know. This Helen wasn’t the same. She was timid, shy and almost scared. She was frazzled by my question. She paused, had no answer. I could see her thinking of exactly how to answer me. What words she wanted to say as to not give herself away.

She then gave up, “I missed you.”

The answered surprised me, but that wasn’t the overwhelming feeling I had. I was for some reason angry. What was I supposed to do with “I miss you.” I had missed her 3 years ago when she just abandoned me without so much as opening my snap chat. And now she missed me?

“You do?”

“Yes.” She said with affirmation. “We used to be really close and I liked that.”

“We did.” I didn’t want to sound bitter. I also didn’t want to give away that I liked her, or used to like her. “It was fun studying together. You were the only reason I didn’t fail all my pre-med classes. Why did you quit?” I was a little bitter.

As soon as I asked that question, I regretted it. She gave me a defeated look. “Jack” was all she said with shame in her eyes. I wasn’t used to this side of Helen.

“Hmm” I groaned. Not knowing what to say.

“We went on that trip and he spent the whole time talking me out of it. He talked about the kids and how they need me and he talked about how demanding his job is and how he needs me. How was I supposed to take care of two young kids and keep going to school. It was unrealistic.” She wasn’t tearing up but I heard her voice break. I felt terrible. I didn’t know it before but the thought of her crying really made me uncomfortable and uneasy.

“I am sure it was the right choice for your family. Sometimes we have to make sacrifices for the ones we love.”

That line set her off. “He never made any sacrifices for me. He never made any sacrifices for his kids.” She was getting mad. “He worked hard, I know that. But it’s easy when you have a devoted wife at home servicing your every whim. He never made sacrifices. He traveled the globe, making deals, trying foreign cuisines and fucking foreign whores till his heart gave out” She suddenly stopped. She had slipped up. She wasn’t supposed to tell me that. No one was supposed to know. She stopped. Looked down at her empty plate and a tear rolled down her cheek.

My anger melted. All I felt was pity. I had held her up on a pedestal all these years. She was strong, wise, dependable… always in control. Now, she was vulnerable, crying in a restaurant into an empty plate of duck breast. I reached out and grabbed her hand. I felt bad. I wanted to comfort her. We stayed there for a min, my hand on hers. Her other hand drying her tears with the table cloth.

Then she looked up. Looked into my eyes. Then… she rememberer something. Her eyes widened. She jumped back. She looked frazzled. “I should go.”

I shook my head in surprise. “Where?”

“I just remembered I had to be somewhere.” She was lying. “They will charge the meal to my account. Thank you for coming. You are a good friend.”

And with that, she grabbed her purse and stormed off.

The last 10 seconds confused me. I sat there in disbelief at what had just happened. I couldn’t help but feel angry. I was fine without her. Three years and she hadn’t pooped into my mind. She had barely existed as a supressed shadow in a crevice in my mind. I had moved on and had no desire to see her again. Instead, she reached out to me. She was the one that texted me. She broke down in front of me. She told me her worries and cried. I hadn’t asked for any of it. I didn’t want any of it. I was happy living elsewhere. Not seeing her. Not being with her. Now, she once again, was all I could think about.

My anger welled up. I had to tell her. I wanted her to know I wanted nothing to do with her. I got up and chased her.

I caught up to her in the parking lot. She was getting into her car “HELEN” I yelled across the parking lot. she looked up and saw me and stopped getting inside her car.

I walked quickly towards her. Angrier in every step. “why did you bring me here, Helen? What did you…” in the middle of my question she grabbed my hand, pulled me towards her, and kissed me on the lips.

It could have been moments later, or maybe years. I regained my awareness, and then my breath. We had embraced each other. She was at eye level with me in her high heels. My hands were around her waist. One of her hands rested on my shoulder where she grabbed to pull me closer. The other hand was on my face. I could feel her body pressed against mine. I felt her. She felt me.

When the kiss ended, she backed up a few inches. Her lips were still open, I could still feel them on my tongue. I could still smell her breath in the air… we paused and looked at each other.

My anger had melted. I realized that it hadn’t been anger at all but rather frustration. All those years I knew I wanted her and I was too scared to admit it, even to myself. She had constantly been on my mind. Every day she lingered and persisted. She had been the standard to which I compared all other girls and they had all fallen short. Up to this moment, she had been unattainable.

But now we stood in each other’s embrace, bodies pressed together. Now I knew she wanted me back. I would never let her go.

I must have let out a smile before I leaned in to kiss her again, but this time she hesitated and pulled back. My heart dropped. Why did she hesitate? Did she change her mind? Did she think she was making a mistake? Was she going to leave me again?

“Not here” she looked around. With that, she grabbed my hand and jerked me around and pulled me towards the hotel. I followed unquestioningly. Into the door, into the elevator, “11” she pressed, then turned around and we kissed again. My mind was on hiatus. What was happening? Where were we going?

The elevator door opened and she pulled me again. Room 1104. She pulled the key out of her clutch. Where had she gotten a hotel room key? She opened the door and pulled me in and closed the door.

She turned around and finally looked at me. I looked back. We stopped for a split second to perhaps ponder what was about to happen. For me there was no doubt that I wanted her. The split second was over. I pushed her against the wall and kissed her. This time the kiss was expected. It was longer, more passionate. My hands first started on her waist. Then I grabbed her back and pulled her closer to me. I wanted to feel her against me. I wanted her to feel me.

We then moved to the bed. She lay on her back and I laid on top of her, kissing her face and neck. She groaned loudly. I was breathing heavy. Then all of a sudden I heard a loud thump on the ground. I looked back and she had kicked off her heels. I watched her feet for a split second and remembered that day in her kitchen how her legs and feet had looked. She knew what I was thinking. She must have. “You want me to put them back on? I know you like them.” She knew I liked them. She must have known the whole time. I didn’t respond and just kissed her again.

After a few minutes she pushed me off and stood up, “unzip my dress”. I reached up to grab the zipper and pulled it down. It revealed the strap of black bra, no clasp. As I pulled the zipper lower, I plunged and kissed the back of her neck and her upper back. She was much shorter now without the heels and I had to bend down to kiss her. She moaned loudly. My hands reached around to her stomach and held her closely. My fingers inched closely to her breasts as I continued to kiss her back and neck. I hovered over her and kissed her cheeks and she turned to me and our lips locked again. She then let my lips go, looked at me and smiled.

With that smile she moved forward a step, turned around and said, “I know you have wanted this for a while.” I felt embarrassed. “I wanted it to too.” A sigh of relief. “But I don’t think you know what you got yourself into.” She smiled mischievously, she then put her hands on my chest, grabbed my shirt and pulled it off in one impressively quick motion. She then ran her French tip nails across my abdomen, smiled and with a violent jerk pushed me back on the bed. I gave in and fell back.

I was motionless, all I wanted to do was watch her, admire her beauty and elegance. Even with slightly messy hair, an zipper dress that was now falling off her shoulder and no high heels she looked elegant.

She reached up to her shoulders and grabbed the dress and slid it down. It revealed a black lace bra that was perfectly sculpted to fit her breasts. As the dress plunger lower it revealed the matching black lace panties. Her body was perfect, flawless, sculpted. She kicked off the dress at it dropped to her ankles and flung it and it fell on then couch opposite the door. I was impressed.

I laid back and watched her as she swayed closer to the bed. My feet were still planted on the ground but my upper body lay horizontally on the bed. She climbed on top of me with a knee on either side. I felt her pelvis rub on mine and she felt my erect cock inside my pants, she flashed another smile. She then reached in between her breasts and unclasped the bra revealing her breasts. They sat perfectly on her chest with the nipples dark and erect at the center. “Touch me!” She said in a breathy sultry voice. I reached up with both hands and grabbed her breasts. Up to that point, I had never known or had imagined that Helen would get implants. She had been such a “body positive” person that I would have never considered it. But then I thought to myself, “that must have been Jack’s doing, that mother fucker must have made get a boob job and then cheated on her. Well now I get to enjoy them.”

“You like them?” She asked almost rhetorically. I simple yes from me would not suffice. I reached up and grabbed her neck and pulled her down forcefully and kissed her. As we kissed she grinded on my leg. She was turned on. She kept grinding against my pants and kissing me as she hovered her body over mine. I then started moved down from kissing her lips, to her neck, and finally to her boobs. I licked one nipple as I grabbed the other with my fingers. She moaned once more.

She then grabbed my right hand and pulled it down to her pussy. Her lace panties had moved to the side in all the rubbing and grinding. She was wet… dripping. I felt it on my fingers. She looked at me and said, “I haven’t been this turned on in year.” That line turn me on more. I wanted her to be turned on. I wanted to satisfy every one of her womanly desires. The line she said motivated me, I held her body in my hands and flipped her over. She was now lying on the bed on her back. “What are you doing?”. I got off the bed then knelt on the ground by the bed. I grabbed her by the feet and pulled her to the edge of the bed. I spread her legs out, looked up at her, “I want to taste you.”

She was surprised by this. I am sure Jack had never bothered to pleasure her. He is a selfish man in real life and thinking that he takes that into the bedroom wasn’t a huge leap.

A prior girlfriend had taught me never to start with the clit. To always work my way up. I started by kissing the inside on her thighs and feeling it against my face. My hands were now cupping her butt and bringing her pelvis closer to my face. I looked up to watch her and she was fondling her own breasts and watching me, pinching her nipples… pinching hard and pulling. I worked my way up her thighs. Her panties were off to the side still but I wanted nothing in my way. With my left hand on her butt I grabbed them and pulled them off. “I am keeping these” I said and put them in my pocket.

“There is plenty more where those came from.” I liked the idea of us doing this again.

I positioned her back and started kissing her thighs again. Then I noticed she wasn’t completely shaved but she had definitely trimmed. She had definitely intended for this to happen. She had sat at home and thought about us fucking in a room that she rented and she had decided to groom her pussy in preparation for me. This thought drove me mad with desire. She wanted me as much as I wanted her. I took the plunge…

I kissed her outer lips and used my left under her butt to position her towards me. I then used my right hand to spread her open. She had thin outer lips and long floppy inner lips. I spread both lips open and started. I started gently at first. Licking slowly and lightly. I could hear her purr under my tongue. She moaned. As I kept going, I picked up the pace. And as I picked up the pace, she got louder. I had never picked Helen to be a screamer, for someone so elegant and graceful. But under my tongue the guys working reception 11 floors down could probably hear her. She screamed and yelled, “Oh God. God yes. Faster” my hear my thumping. I loved making her feel that way. I would be forever pleased if I could kneel at the edge of her bed and make her scream like that. When she finally came she pulled her knees together and jumped back in a shaking fit. Her eyes had rolled into the back of her head and let out a moan.

She lay quite in bed for about a minute to recuperate. She had to catch her breath. I was proud of my work so I sat back and watched her. I wanted to make her happy like that. I wanted to please her. When she came back to, she looked at me and smiled. I smiled back almost smugly.

She stood up and tried to stand on the bed but her left leg gave out. She was weakened by the powerful erupting orgasm. I laughed out loud. She tried again and succeeded. As she stood on top of the bed she signaled me with one finger to come close. I joined her. She then kissed me, tasting her pussy on my breath. After that she knelt down on the bed and began to undo my pants. I knew what was coming and I welcomed it, payback. She pulled out my pants and then my boxers. “You are huge.” She said.

I had never been really a “big” guy. Average at best. I had certainly watched my fair share of porn and knew where I stood. But the way she said that made me believe her. It is possible that she had not been with many guys and that she doesn’t watch porn. Or maybe it was that Jack wasn’t very big and she was used to him. But the way she had exclaimed it made me believe her, and I loved her for it.

She grabbed my cock at the base in amazement. She looked like she was contemplating what she is about to do. I couldn’t help but watch. At first she stuck her tonight out and licked the head. It was rather cute. She looked like a cat who was shyly and cautiously trying something foreign to her.

As she was doing this, I had a realization. That realization was that I did not want to wait anymore. I wanted her. I wanted to feel her. I wanted to be in her. I knelt down from my standing position on the bed. She looked at me not knowing exactly what I was doing. I grabbed her by the shoulders softly and I laid her down on her back. Her long hair was spread out behind her head on the bed. She looked up at me with a facial expression that expressed affection and trust. No one had looked at me that way before. I slowly climbed on top of her. My dick still had her spit on it but she was still very wet. I slowly started to insert my penis in her. As I first entered she gasped slightly, I kept going. When I was all the way inside, I stopped. I felt a strong connection to her at that moment. I was inside her and she felt me in her. This had been a moment that I thought about for years but now it had happened and I was in disbelief. I looked into her eyes again and I kissed her deeply.

As we were kissing, I slowly pulled out. Not all the way. I’ve been slowly pushed my cock in her again. Then out and back in again, then all the way out and back in again. With each thrust I gain speed, with each thrust I felt closer to her. We continued to make out furiously as I fucked her harder and deeper with every thrust. She was morning. I was focused. Beads of sweat fell from my forehead onto her neck and mixed with her sweat. I was thrusting hard, with all my effort. She grabbed the back of my neck and pulled me closer to her. Her mouth was on my ear. She slowly nibbled on my ear lobe and the seductively and quietly whispered, “let’s slow down, we have all the time in the world”.

With that I started to think, “we do have all the time of the world. She is going to leave Jack and come away with me. We would move in together near my new job. I would work to support her (not at the same standards she had with jack, but reasonably well) and she would go back to school. Her kids can stay at boarding school.” My naive mind built our future together. Nothing else mattered as long as she was with me. My parents would not be ok with me being with a 38 year old woman but they know and love Helen. They would get over it eventually. My future was with her.

She slowly pushed me on my back and I rested my head on the pillow. It was now her turn to ride. With her right knee on side of me and her left foot on the other she positioned my cock at her pussy. She spit on her hand and rubbed the head of my cock with it. She brought down her left knee to the mattress pushing my cock deep inside her. In the position she slowly and deliberately moved backwards and forwards with my cock slowly sliding in and out of her with every slide. She grabbed her own tits and fondled her nipples. She then fell forward and lay on top of me. In the position, her clit was rubbing on the hairy triangle on top of my dick and she felt it. She moaned. He thrusts quickened. She moaned louder. Then quicker. I was getting close. Louder. Quicker. Louder. Quicker. I had to hold on. She was now screaming then shaking. She was cumming again. I was watching her. She kept thrusting, shaking and sweating. “I am gonna cum”. She didn’t hear me. “Helen, I am gonna cum.” She finally came back. She couldn’t stand up and pull me out so she fell on her side on the bed. I grabbed my cock to jerk off and cum.

“No. That’s for me.” She put her mouth on the head and stroked my cock hard and fast. I came instantaneously in her mouth. When she let go, none of it was still in her mouth.

We both crumbled on the bed in each other’s embrace. We were spent…

We stayed in bed for another hour, chatting, cuddling and making out. It felt perfect. Perhaps we should have, but neither one of us felt guilty. We talked the same way we used to talk when we met up on Mondays.

We met up again the next day and had sex. Then I flew back home. Jack ended up pulling through. He got another operation and was back at work by later February. He was back to cheating on Helen by early April. She didn’t care. She had me. Every other week or so she would fly over and see me and spend the night and fly back.

Source: reddit.com/r/sexystories/comments/ceq3r1/helen_in_high_heels_part_iv_mf_long