Working with Older Female Co-Worker

I work for a corporation in a big city. I have always loved living in the city. I grew up here and have never wanted to leave until recently. The cost to rent a one-bedroom apartment eats away at my bank account and forces me to do contract work during my time off. With my thirty-fifth birthday on the horizon, I finally made my mind up to buy a place in a suburban area located on the outskirts of the city. Problem is, I don't know many people who live in the suburbs. I started asking around the office for people's opinions on the best place to move and getting different opinions.

One day a co-worker named Betty came into my office and asked, "Hey Jim, how's the suburban search going?"

"Hey Betty, nothing yet. I'm struggling on where to look."

Betty is a nice lady, has been married to her high school sweetheart, and has been with the company since she graduated college. She has the look of an old school librarian, glasses, short, chubby but not overly heavy woman. On occasion, Betty would wear tight-fitting clothes, and I would notice her hips or breasts and think, not bad for a fifty-three-year-old woman. Everyone liked Betty, and she was perpetually a nice woman. Kind of like having your nice aunt always being around.

"I don't know if you would be interested, but there is a unit for sale where my husband and I own. It's a one-bedroom unit and always quiet there. I know the seller and could set up a showing if you would like?"

I had to think for a minute, do I really want to be that close to someone I work with? Especially, Betty, I like her, but she is a square woman, who probably has never done anything exciting in her life. I like to have random women over and tend to stay to myself wherever I have lived. I also didn't want to hurt her feelings, so I said, "That would be awesome. Think you could set it for Saturday?"

"Yes, do you want to exchange numbers, so I can get you the information?"

Betty and I exchanged cell numbers. I asked Betty if she preferred text or actual calls?

Betty gave me a funny look and replied, "Jim, I may be old, but I do know how to text. How old do you think I am for Christ's sakes?" Then she smiled and winked at me. While walking away, I sent her a sad face emoji. To my surprise, she sent me a kissing emoji.

Did she just flirt with me? That was the thought in my head. I went about the rest of my day.

On Friday, Betty approached me in the hallway at work to tell me, "Hey Jim, the owners are going to show you the condo on Saturday at six PM, does that work for you? I can text you the address and meet you there if you want? It is in the same building as my condo."

"That is perfect, Betty. Thank you very much! Are you sure you don't mind being neighbors with someone you work with though?"

Betty's response was actually pretty funny, "Jim, I wouldn't want to live in the same zip code with most of the people we work with. You are the only one I would not mind having as a neighbor. You are a sweet young man."

I met Betty about twenty minutes before six. She came out to the parking lot and told me, "Come on in. You are early, we can hangout in my place for a few."

Betty's place was exactly what I thought it would be, plain. The actual condo was genuinely nice, but the décor was simple and generic, like Betty.

I liked the condo and made an offer on the spot without thinking. I asked Betty if it would bother her being neighbors with me?

Betty's response was, "Absolutely not. You are a sweetheart. Please don't tell people at work that I said that."

"Well, it looks like we're going to be neighbors, so we should get used to complete honesty with each other." We both laughed, and I went back to my apartment in the city.

The whole process of purchasing the condo took about a month. It was finally over, and time to move in. I decided to take a few days off from work to get settled in my new place. To my surprise Betty was checking in on me and made me dinner my first night there. I was thinking I could get used to someone cooking for me.

Then Betty asked me, "Do you want me to call in sick to help you finish getting settled? I think in fifteen years I've only called in once."

I didn't know how to react to that question. I could use some help, but it would be Friday, and I still had the weekend to finish up. I quickly went back and forth in my head, then finally said, "I don't want to take advantage of you. Plus, I'm sure your husband wouldn't want you hanging with me all the time."

"My husband doesn't care, as long as he doesn't have to do anything. You would not be taking advantage of me. I need things to do, and you are fun to be around. But don't tell people at work that I called in to help you. You may not realize this, but they all like to gossip there. I don't want to be a part of that. Deal?"

I thought this is going to be a big help for me to finish everything. Selfishly, in the future. "Deal, Betty! I am already like being neighbors with you."

Betty helped me unpack and organize my belongings all day Friday and Saturday. I couldn't believe how much we got done in two days.

On Saturday night, I ordered takeout for us to eat, and we both just sat on the couch talking and finding out about each other's lives. Betty made me aware that her husband wasn't around a lot, and when he was, he had no interest in spending any time with her. I felt bad hearing this. She went on to tell me that it had been years since there was any intimacy in her marriage. Then told me, "Don't worry about me sharing any information about women coming to see you here. I won't be telling the gossipers anything. They have already started saying they want updates."

I jokingly asked Betty, "What happens here stays here, right?"

Betty responded, "Absolutely! Deal! But if I'm going to be hanging out here, you are going to need to get some wine next time."

I put the TV. We sat on the couch, exhausted from all our hard work. Betty looked tired, and I felt horrible that I had exhausted her on her days off. We both dozed off. I woke up about three in the morning, and Betty was laying down with her feet on my lap. I wiggled her feet and asked her if she needed to go home? Betty said, "I don't have to, and I really don't feel like getting up. Do you care if I stay here?"

"No, not at all, Betty. I'm going to head into my bed. Feel free to join me if you want." I was joking when I said she could join me. I went into my bedroom, and when I turned around, I realized she was literally coming into my bedroom. Betty climbed into the bed and went right to sleep.

I woke up the next morning to a note on the kitchen counter. "Hi Jim, thank you for letting me get some rest here last night. Just a thought, we can carpool to work if you want. Just send me a text if you want to. I'm giving you a break from hanging with the old saddlebag today. Enjoy your Sunday!"

I texted Betty that I would like to carpool into work with her.

On Monday morning Betty, and I were joking about her spending the night at my place. During our ride into work. Betty said, "When I woke up, I didn't even remember how I got into your bed. Thank you for not taking advantage of me."

We both laughed at that comment. I told Betty, "I can't promise I won't in the future."

Over the next few months, Betty and I would talk our entire ride into work and on our way home. She was a totally different person than she was at work. We would make plans to hang out and watch TV or have dinner a few nights a week. Betty would occasionally fall asleep at my place, and I would let her stay. It was almost like having a roommate.

On a Friday, during our drive into work, Betty informed me, "There is a rumor that you used to do massages when you were working your way through college. Is that true?"

I started laughing, "Jeez Betty. How do people at work find this stuff out? I did do it when I was younger. The money was good, and it was better than waiting tables. These people at work should open a private detective company. They seem to know everything."

Betty then stated, "Well, I think I earned a massage. If I knew this sooner, I would have had you give me one when you worked me to death organizing and unpacking your stuff.", then she laughed.

I explained to Betty, "You do realize that that you'd have to take your shirt off for a massage, right? I don't mind doing it. I just want you to be aware of what you need to do for a massage."

"I'm OK with that. I'd be laying on my stomach so you wouldn't see anything. Plus, I wouldn't want to scar you for life by seeing me topless."

"Don't be silly. I'll tell you what I'll do it tonight. Unless you have big plans for the weekend and are going to blow me off." I intentionally avoided the topless comment. I didn't want to come off as mean, but I didn't look at Betty like that.

"OK, good. I'm looking forward to this. Do you mind if I bring some wine? I know I talk a lot, but I'm really all talk. Taking my shirt off and allowing a man to touch me, no matter how innocently, makes me nervous. I'm going to tell you the only person I've ever been intimate with is my husband. I realize that we are not going to be intimate. Letting someone touch me is intimate. I hope I'm making sense and not just rambling." It was obvious that Betty was nervous and really overthinking this.

"Don't worry, Betty. We are friends. I don't want you to be uncomfortable. You can do whatever you need to be comfortable. This is supposed to be fun, not stressful. OK?"

"You're right! I am looking forward to getting a massage. How's nine work for you?"

"Nine works for me. Gives me time to get some massage oils." I felt bad because if I canceled, I was afraid I'd hurt her feelings, and the stress of doing this had her off her game all day. Dammed if you do, dammed if you don't. Our ride home was quiet.

As we entered our building, she said, "See you at nine, right?"

To help ease her anxiety, I smiled and replied, "Yup. Can't wait to help relax you." I watched as Betty's face turned, beat red.

At nine on the dot, Betty knocked on the door. When I opened it, I noticed Betty seemed to be buzzed. As she came in, she said, "Yes, I started the wine a little early. I figured a t-shirt and sweats were the appropriate attire for tonight as well. Should I go straight to the bedroom, get on the bed, and take my shirt off?"

I laughed, "Yes, Betty. Listen, we don't have to do this if you are uncomfortable. Also, you aren't the only one who started drinking early. I've had a few shots of tequila and a few beers. I hope that's OK?" I was nervous too. I felt really bad that she was having anxiety caused by me.

Betty went into the bedroom to take her shirt off to get ready for her massage. Then, she yelled out to me, "Hey, I'm ready. Come rub me."

I went into the room and figured I'd start with a warming oil for the beginning of the massage. I squirted it on Betty's back and started rubbing it into her skin. Once I got it all on her back, I decided it would be easier if I got on the bed to start the deep massaging. Betty was facing away from me to avoid any comfortability she was having. As I started to go into deep massaging, I could feel the knots she had from all the stress she had. I finally started to feel her loosening up the more I rubbed through her knots. I asked her, "How am I doing? Feeling better?"

As Betty turned her head to face me, she stated, "Yes, that feels AMAZING!"

I was relieved that she was more comfortable. "Good, I'm glad." I continued to rub her entire back as I got closer to her waistline, she would flinch. The flinch caused me to continue to rub that area of her back. I would slowly slip a finger into her waistband to see what her reaction would be. I wasn't sure if she was aware because I wasn't getting much of a reaction from Betty. So, I decided to slip my hand into her waistband, with my hand obviously touching her ass cheek. To my surprise, her hips bucked up slightly. Now I was curious how far I should push this. I continued to explore with no resistance. I rubbed deeply on her ass cheeks. At one point, I believe I heard a moan from Betty.

I asked Betty if she would like me to rub her feet, she responded, "That would be great. Do you mind doing that?"

"No, I don't mind at all. I promised a massage, so wherever you want me to massage, I will." I then moved to the bottom of the bed and rubbed massage lotion on my hands and started in on her feet. I was feeling like I screwed up by moving away from massaging her back. I was curious how far Betty would have let me go if I had continued to push the envelope.

As I was doing a deep rub on the arch of Betty's feet, I heard her say, "That is so amazing. I don't remember ever feeling this good. Would you mind rubbing my legs too?"

I explained, "I don't mind, but do you want me to rub through your sweatpants?"

It was obvious Betty had not thought that request through. Surprisingly, she said, "You're right. That probably wouldn't feel as good. What do you suggest?"

"I think we can take the sweatpants off. I can get a towel to cover your ass. What do you think?" Here I was, pushing boundaries again. I couldn't believe how excited I was getting with this cat and mouse game with Betty.

I waited for Betty's delayed response. All I could think was, I went too far. Then Betty asked, "We wouldn't need to take my panties off, right? I'm ok with the sweatpants coming off, but I'm too insecure to completely naked. Plus, I'm tipsy and have a habit of falling asleep here. I don't want to wake up in the morning naked, not remembering what happened." I could tell she was being sincere and was nervous about what was happening.

"No, there's no need to take your panties off. Wait here. I'll go get a towel for you. Drink some wine, and I'll be right back." As I walked away from the bed, Betty started guzzling wine. All I could think about was how to get her completely naked on my bed. The fact that I know how inexperienced she is sexually drove me insane.

I came back in the room expecting Betty's sweatpants to be off. As I approached the bed, I jokingly said, "looks like I'm doing all of the work. I guess I'll take the sweatpants off."

I fully expected Betty to remove them. To my surprise, Betty informed me, "Yes, you are. I'm just way too comfortable to do anything. I'm enjoying myself for once."

"Good, you should enjoy yourself. I don't mind doing all the work." I couldn't tell if her wine was getting to her. Betty was totally relaxed, without a care in the world. I slipped my fingers into both sides of her hips, making sure they hooked both her sweatpants and panties. I started to pull them down, expecting Betty to stop me from removing her panties. There was no attempt to stop me. I believe she was oblivious to the fact that I had removed them. I asked, "How's that, better?"

Betty shook her head. Once again, I squirted the oils on her legs and started rubbing from her calf up to her thigh. It was obvious that she was enjoying this. I never put the towel over her ass, and there was no protest over this.

I honestly believe that she was unaware that I had removed her panties. Betty parted her legs slightly. I bent to see if I could see her pussy. I could not because her thighs were thick. I decided to ask her, "Would you like me to get the inside of your thighs?".

Betty just nodded in a yes motion to me. I pulled her legs further apart and looked again. I could now see her pussy in plain view. I could tell it was moist as I started rubbing the inside of her thighs. I asked, "Does this feel good?"

"It feels amazing. If I knew how good a massage actually was, I would've been getting them sooner." Betty didn't seem uncomfortable or nervous that my hands were moving around her thighs and inching closer to her pussy and ass.

I inquired, "Your husband has never done this for you?"

"No, he hasn't. I don't think he even understands how to be intimate. We come from a different generation, Jim. I admire your generation's openness when it comes to intimacy and attention to the details. You obviously pay attention to the details of a woman because your hands are magic. My husband avoids everything at this point in his life. That's why I'm able to hang out with you all the time and do sleepovers. But he's the only man I have ever been with, and I'm ok with that, now keep massaging. Enough with the depressing part of my life." Betty then started to giggle. Betty's legs slightly opened more, and her ass jiggled while she was chuckling.

I announced, "No problem. No more depression talk. Tonight, I will make sure you are taken care of. Full body massage on its way."

This time, I had positioned myself between her legs. I made my mind up to see how far I could go. Betty shared a lot of information, and I was curious about what I could get her to do. The thought of her not having had sex in years and fucking her to orgasm was really turning me on.

I then started rubbing Betty's back again. As my hands moved up her back, I continued to her head. I rubbed her head while my crotch rested against her ass without protest. I yanked her hair slightly to see if I could get a reaction. Betty's ass sprung up as she moaned.

Softly, Betty mumbled, "I never had that done to me."

In a low tone, I asked, "Never had what done to you?"

"Had my hair pulled like that," Betty responded.

"Did it feel good?"

"Yes!"

I told Betty, "How about you just enjoy what I am doing for the rest of the night? No questions asked, OK?"

"OK, I will try." I could tell Betty was feeling lost in everything I was doing to her body.

I continued to rub her back, moving down to her lower back. Betty's hips were slightly moving from side to side. I moved my hands to her ass, rubbing deep into her ass cheeks. There was no protest. I started to slide my fingers up and down her ass crack. I could see Betty breathing heavily. She looked at me. I could see her eyes were glazed. I asked her, "Are you OK?"

In a low murmur Betty, simply said, "yes." Then put her face into the pillow.

I pulled her ass cheeks apart and ran my tongue over her asshole. I felt Betty's body jerk and saw the goosebumps form all over her ass. Betty lifted her ass and was practically kneeling in front of me. Inviting me to do whatever I wanted with her body. I ran my tongue from her asshole down to her swollen pussy lips, burying my tongue in her soaking pussy. Betty let out a loud moan as her body tensed up.

"Feel good?" I asked.

Betty responded, "YES! AMAZING!"

"Good. Let's stop fucking around and denying what is happening tonight. Turn around." I commanded.

"OK. What is going to happen tonight?" Betty innocently asked me as she turned around and was kneeling in front of me face to face, completely nude.

"Betty, we are going to have fun. I am going to make you feel like you never have before." I grabbed her hair slightly forcefully, pulled her into me, and started aggressively kissing her. There was no resistance from Betty. I reached my hand down and started rubbing her swollen clit, noticing she was completely shaved. I could tell she was going to cum soon, so I pushed down on her back, commanding her, "open your legs!" Betty did as I told her. I sucked and licked her clit, slowly fingering her pussy.

I could feel Betty getting ready to cum when she suddenly jerked forward and screamed, "OH FUCK! FUCK, FUCK, FUCK!" Betty exploded all over my mouth and finger. Her legs were trembling so much I thought she was having a seizure.

I knelt up, asking, "Are you OK?" I could see in her eyes she was in complete ecstasy. Her body was shaking, but Betty was smiling with her hands on her head, with a look of disbelief.

"YES, I AM! I can't believe I used that language. I can't believe this is happening. I feel guilty, but it feels really, really good."