One day during a lunch break with Casey I found myself asking her about her long term plans. We had gotten fairly close and I found that I care about her. She was doing an amazing job running my business for me but I felt that her talents were wasted as a secretary in a construction company running out of a small dusty office. It was obvious that in the time she had worked here she had come into her own, I can’t really describe it. She was more confident, and capable with every passing day. Perhaps a little more well-rounded. Everyone instantly loved her when they met her. And not just because she was a hot young attractive girl, she was very likable. Even Mary who was insecure because of her told me how much she liked her. “Are you going to apply to college again?”
“I don’t know.” She said. “Probably not. I just don’t know if that’s my path anymore. Also, I may or may not have used the money I saved for something else.”
That was a little disappointing. I leaned back and threw my hands in the air. “Like what?”
“Just some alterations I needed done.” I didn’t know what that meant but I was more annoyed by the fact that she spent the money.
“Look Casey, I cant deny that I love having you here. You have made my life infinitely easier. Losing you would be devastating. But I think you are meant for more. You are smart. Calling vendors and coordinating call guys is a waste of your time and talent.” I felt that I was pushing too much now and didn’t want to upset her. “Look I am sorry I am saying all this. I don’t mean to be pushy. But I just want what’s best for you.”
“What would you do without me?”
“I don’t know. I will probably hire some shlup who is going to take twice the time to learn the job and then do it worse.” She laughed. I was glad she laughed. I didn’t want to upset her.
“Oh so that’s all I am to you? An employee?” That question caught me by surprise a little.
“No, of course not. But we would stay in touch. Who is gonna bring me soup when I get sick again.” I didn’t know what to say. “You are like an important part of my life and whatnot.” I think I blushed a little.
“I am glad I am not just ‘an employee and whatnot’” she was mocking me now. “But I have been thinking of trying to pursue something else. I was never really that passionate about psychology anyway.”
“Something Like what?”
“Modeling…”
That was another surprise. She had never brought anything resembling this up before. One thing was certain and plain, she was beautiful. And she had only gotten prettier since I met her. I found myself looking at her now. Her pale complexion had complemented her dark black hair. Make up, as always, done perfectly. Her eyes lined and popping out. She had hazel eyes. She also had an amazing figure. This had been something I had noticed before and tried to push away and out of my mind. When I first met her she was very slender but over the past year she had filled out and taken on more of a “womanly” figure. Or maybe it was just the way she dressed. I wasn’t sure. I felt guilty just having that thought.
I realized I hadn’t said anything in a while and was perhaps looking at her for too long. “If that’s what you want to do.” That didn’t come out too encouraging.
“You don’t think I am pretty enough?” She looked somewhat upset.
“Oh no no.” I jumped to correct myself. “Don’t get me wrong. You are gorgeous. You really are. You would have an easy time finding a job, I am sure. I am just surprised that’s all. You never mentioned it before.”
“Yeah. I have a girlfriend who knows a guy. He says I am probably a little on the older side but that there is a niche for special girls like me and that can help me break in and get some gigs to get started.”
I already didn’t like that “guy”. He sounded sleazy. What did he mean “special” girl. I bet that’s what he says to all the girls to have his way with them. “Just be careful, Casey. Jobs like that have a lot of predators and sleazy people that want to take advantage of a gorgeous girl like you. I just worry about you.”
She reached out and caressed my thigh. “You are sweet. I promise I will take care of myself.”
A month after that conversation, she gave her 2 weeks notice. She was going to move to NY. She had already gotten a few gigs.
We stayed in touch. She sent me some of her work in the mail, signed. The first one was one of those furniture flyers that you see in the mail and toss out. She was sitting on a couch in pajamas. The couch was $1200. She signed it, “to my favorite Teddy”. I saved it
A couple of weeks later she called me. We chatted for about 45 mins. She was enjoying herself and having lots of fun. She had sold her car. Didn’t need it in NYC. She was living with 3 other girls in a 3 bedroom apartment. She was in the living room, it was “temporary arrangement”. She said she was trying to break it but the people aren’t as open-minded as she thought they were. She said she met a couple of producers who had the “wrong idea” about her and she had to walk away. I was happy to hear that.
She asked me about the business. I was in shambles but I didn’t want her to feel guilty so I downplayed how much I was missing her at work. I also downplayed how much I was actually missing her. She had somehow filled my empty life and now that she was gone, I was the single 42 year old guy again. I told her to stay safe and to take care of herself. She said she is.
We spoke a few more times and she kept updating me on her career moves. She had a TV commercial for some local car dealership. It’s aired at like 3 pm in the area where the dealership was so I couldn’t see it. But she sent me a YouTube link. She was dressed in a skirt and a top that showed off a lot of cleavage. It wasn’t classy. The ad drew all the attention to her chest. It upset me. I had never seen her like that before.
On her next call she was a little more stressed. She was running out of money and those small ads weren’t making her a lot of money. I offered to send her some money. She was quiet for a few seconds and I heard her sob. “Oh Teddy. I can’t take your money. But it’s so nice of you to offer. I know I can always count on you. You are the sweetest.” When we hung up I was worried about her. She didn’t call me back for a few weeks after that. I tried to call her but she didn’t respond. I got another letter with another ad for another car dealership. She was in a bikini next to a Chevy Impala. “Love -Casey. P.S. don’t worry about me, I am doing good.” It was signed.
For a few months after that I didn’t hear from her. I figured she had made new friends and moved on to bigger and better things.. or at least that what I hoped for. But one February night I got a call from an unknown number at 8 pm. It was Casey. She was at the bus stop and asked if I could pick her up. “Yeah, I will be there in 20 mins.”
When I got there she was waiting for me outside. She looked shaken. She wore a sweatshirt that was too big for her and jeans that were ripped (but I think that’s a style). It was freezing outside so I let her in the car. She hugged me and I drove off.
I started to drive to her parents but she said, “can we go to your place?”
“Sure, of course.” She was shaken up about something. I didn’t want to push her into talking. When we got to my condo I let her into the extra room. “Why don’t you take a shower while I get some pick up.”
“That’s ok. I am not hungry.” She showered and slept until 6 pm the next day. She woke up when I came home from work.
I stayed clear from asking questions. I figured if she wanted me to know then she would tell me. We hung out that night. She was closed off at the beginning but as the night went on I was seeing more and more of the Casey I know and love. We orders pizza and started a movie. After we finished the pizza she got up and washed her hands and brought a cover (she knew where everything in my house was). She sat next to me on the couch and spread the cover over the both of us and rested her head on my shoulder. I raised my arm and took her under. She looked up at me and smiled.
The movie was long and we both dozed off. As it ended I woke up but she was asleep. She looked peaceful. I didn’t want to wake her. I slowly laid her on the couch, covered her with the blanket and went to my room.
I had a strange feeling that night. A feeling that I have tried to fight off in the past. But I quickly dismissed it. She sought me out in a time of need. These thought I had were cowardly temptations to take advantage of a vulnerable person.
As I tried to shove those thoughts out of my mind, a light knock came at the door. I got up and slowly opened it. She was walking away but when I opened she turned turned back. “Sorry I didn’t mean to wake you up.”
“I wasn’t asleep.” She looked frazzled. “What’s wrong?”
“Um. Nothing urgent. That’s alright. I am sorry. I shouldn’t have come in.” I saw the same uncertainty in her eyes that I felt earlier. Or maybe it was wishful thinking.
“That’s alright, Casey, come in. Let’s talk. Tell me what you are thinking.” I gently grabbed her hand and set on the bed next to me.
She slowly began to talk, “I am just really grateful to you Teddy.” I smiled. “You have been such a good friend. You didn’t have to do any of this. You opened your home to me. You offered your money to bail me out. I just don’t know how to thank you.” She was looking down.
“You don’t have to thank me, Casey. I am glad you trusted me and came to me. I am really happy to be here for you whenever you need.”
“It’s not just that. I want to say thank you for believing in me. You pushed me to be better even when it meant that I would stop working for you.”
I tried to make a little light of a tense moment. “To be honest, I am regretting that a little.” She smiled. “Things are a bit messy. So needless to say, if you ever want to come back. My door is always open.”
She finally raised her gaze and looked me in the eyes. “I would love to.”
I caught her gaze and said “please come back.”
We both slowly leaned in at that moment and kissed each other. It was a hesitant kiss. I felt her soft lips quiver as they touched mine. I momentarily remembered who we were and snapped back.
“I am sorry.” I apologized quickly. “I shouldn’t have done that.” I wasn’t even really sure if I did anything.
“Don’t be.” She said with conviction. “I am not.” I stayed silent. “Teddy. You have been the only constant in my life for the past 3 years. You treat me well. You are kind and caring. You believed in me and even when I decided to go, you still cared about me. I am not sorry about this at all. In fact, I have wanted to do it for a while and I don’t regret it. Do you?”
Her conviction inspired my own. “No”
We both leaned in again for a kiss that was much longer and more passionate. Her lips were soft but forceful. We sat next to each other on the bed, our bodies turned towards each other and our lips locked, she reached with her left hand and put it on my thigh. I put my hand on her forearm as she touched me and reached up. Her hair had come down and covered her face. I brushed it back. I wanted to see her beautiful face as we felt each other.
She smiled at me and reclined back a little as I continued to kiss her neck. Her skin was soft as I felt it on my lips. I could see her nipples peaking through the shirt she had borrowed from me. “That tickles.” She said as she pulled back a little and gave a playful chuckle. As she stood back up she reached up and grabbed both my shoulders and with some force she pushed me back on the bed. Her movement with swift and it took me by surprise. She was an assertive girl overall so I shouldn’t have been that surprised that she was also assertive here. But it did surprise me. It didn’t help that I was shy and scared. I knew I wanted her in that moment but I wasn’t sure how far she wanted to take things. I was happy to follow her lead.
Once I was flat on the bed she climbed on top of me. We counties to kiss, more passionately now. Her hair draped all around us as we continued to lock lips. I could feel her body rub against mine. She could feel me too. I was hard. While kissing she reached down her hand and put it down my pant. I felt her long slender fingers grab the head of my cock. “Oh Teddy.” She said. Her sultry voice drove me crazy in that moment. I grabbed her face closer to me and kissed her more. My hands slid down and tried to feel every inch of her body. But she had other plans…
She moved her lips down from mine to my neck and chest. She was totally in control and running the show. I didn’t want to get in her way. She slid her hands under my shirt and slowly pulled it up revealing my hairy and greying chest. She laid her head on my chest as if listing to my heart beat. It was beating fast. When she finally lifted her head she stuck her tongue out and licked my left nipple. A shiver ran in my spine. It was unexpected. She felt my body react. She smiled and kissed my stomach continuing her journey down.
With both her hands she reached and grabbed my pants and underwear. She looked up at me and our eyes met again. She gave a devilish smile and pulled them down. I lifted up my butt slightly to help her. As she pulled my cock flopped out of my pants. “Well that’s certainly a pleasant surprise.”
I am really not that big. I never measured. Or maybe I did when I was in high school but it never came up in recent years. On Mary and I’s first time she was in pain, but I attributed this to inexperience. But Casey was definitely pleased. That’s all I cared about. I wanted to please and pleasure Casey. But she had another idea in mind. She grabbed my hard cock at the base and took the whole head in her mouth. I felt her wet tongue wrap around my head and go in a circle. I heard myself moan. It has been not only years but decades since had someone do that to me. Mary had given me a blow job once when we were dating and then once right after we got married. It was clear that she didn’t enjoy it and I didn’t want to ask her for something that she clearly hated so much so I never asked.
Casey was definitely not hating it. She played my cock like a fiddle. She spit in her right hand and she stoked my shaft rhythmically as she bobbed her head up and down on my head. Her left hand massaged my balls lightly. “Oh fuck, Casey.” I let out from the midst of my pleasure.
“That will come a little later.”
I couldn’t help but laugh a little. Her feisty personality carried into the bedroom I see. In the midst of that thought I felt myself well up. I was getting close. I could feel my body tighten. I reached down and put my hand on her right hand (the one that was stroking my cock. “Well if you want that to happen then you might have to slow down a little.” She pulled her lips off my cock and I could see that she started to think about what to do next. As she stood up, she stuck her tongue out and gave the head of my cock one more lick.
“Let me get a little more comfortable then.”
I can’t deny I had thought about this before. She had a perfect body that only became more perfect in the years since I have known her. She slowly reached down and grabbed the shirt she had on at the bottom, my shirt. She maintained eye contact with me as she slowly and seductively pulled up her shirt. Her gaze made a little shy so I broke eye contact and when I did, my vision fixated (almost involuntarily) to the edge of her shirt as it climbed up.. inch by inch revealing her flat belly.. inch by inch.. soft skin.. inch by inch.. the rising mounds of her supple breasts.. and then her nipples. The shirt left my periphery as I fixated on her perfect breasts. Her areolae were pink and slightly darker than her skin. Her nipples were small and barely rose from her chest.
“You like them?” Her voice broke in and woke me up.
“I do.. a lot.”
“I thought you would. I thought about you when I was getting them.”
“You did?” I didn’t understand what she meant then. She inched closer and closer to me and as she got close she again straddled me as I sat on the edge of the bed.
“They want to say ‘hi’.”
I lifted my right hand and gently grabbed her left boob. As I did that I felt small, barely noticeable bumps that lined her areolae. I looked closely..
I closed my mouth that was inches away from sucking on her right nipple. “Wait, are you trying to tell me.. that..” I hesitated.
“Yes.” She chuckled. “I had some ‘alterations’ done. I am surprised you didn’t notice.”
I hadn’t. Should I say that? Is it bad? Is it good? I don’t know.
“You were always a gentleman. You never checked me out like the rest of the asshole working around you. That’s why I like you.” She was running her hand though my hair as she sat on my lap with her legs straddling mine. She leaned down and kissed me. This kiss was more gentle and emotional. She really did like me. I liked her too. Since the day I met her she has captured my interest. She had a fire in her and that fire kept me warm.
As we kissed I ran my hand on her back. Her skin was warm and soft and I felt a bead of sweat drip down on my hand. I felt the contour of her body. Her spine under each of my fingers. I found my left hand creeping up and grabbing her neck from the back. Gently. The muscles of her neck moved as she kissed me. My right hand plunged deeper and into her pants. As she felt my fingers creep down to her ass she let out a moan and looked up. I leaned in licked her right nipple as I intended to do earlier. Her moan got louder. She leaned over again and started to kiss my left shoulder then she raised her head up and whispered in my ear, barely audibly, “I am ready. I want you in me.”
As she said this she slowly slid off my lap and stood back up. She turned around and started to drop her pants… my pants… that she was wearing. She moved quickly now, it wasn’t slow and seductive like before with the shirt. She bent all the way down as she dropped the pants to let me see her ass. She wore pink panties. They weren’t supposed to look sexy but the color really turned me on. Or maybe it was how they contoured her ass perfectly. The pink made her curves pop. I couldn’t wait. I reached out and grabbed her by the hip and pulled her down on my lap. She laughed as she fell back on me with the pants still around her ankle. She leaned down and slipped one pant leg past her ankle and then used the other foot to kick the pants away. They flew and landed on my dresser.
I was kissing her back still and she sat back up I was kissing her neck, she leaned into me and arched her back. She moved her hair to the opposite shoulder. As she did that I reached from under her arms and grabbed her tits. I watched as my hands cupped both tits from the bottom. They sat perfectly in my hands. As I lightly squeezed them my eyes trailed down again to her bright panties. She flexed her hip forward and grinded on my erect cock. I watched the motion of her hips. In between her legs I saw a mound. Her panties were stretched across her bulge. From the top of the panties I saw a head peaking out. A head of an erect penis. I stopped kissing and my eyes opened wide and my jaw dropped.
“O my god, Casey..
Source: reddit.com/r/eroticliterature/comments/japoyg/midlife_crisis_part_2_mf