My First Time With an Older Woman

My First Time With an Older Woman

At 18, I had my first experience with a much older woman and it changed me forever

Image for postImage by Mabel Amber from Pixabay

Before I begin, it is important to remember that where I grew up, the age of informed sexual consent irrespective of age is 16 ? so the fact that I was 18 when this happened is perfectly legal and something I was and am comfortable with.

When I was 17, I had a girlfriend named Stacey who was a year older than I was, but we?d been friends for as long as either of us could remember.

Something changed as we entered our later high school years, the pretty girl with beautiful long hair and freckles that I grew up playing hide and seek with around the neighbourhood turned into a teenage model, with incredible bone structure and a body that teenage boys stared at as she walked past.

I was a popular guy in high school ? athletic, smart and witty, I attracted the cheerleaders and the nerdy girls.

Stacey was somewhere in the middle, she wasn?t athletic enough to be a cheerleader and was a ?B? student, but she had an absolutely acerbic tongue which could spew venom when she turned her mind to it.

Teenage me found that biting aspect of her personality more attractive than every other feature about her.

She Made Me an Accessory

While she was the ?it? girl at our school because of her budding modelling career (which went nowhere as she moved out of her teenage years), she didn?t seem terribly interested in guys.

I think it?s a myth that all teenage girls sit around and think about their wedding or which boy will ask them to prom.

Stacey really didn?t care about that stuff.

She did care about how she was perceived by other people though and as she entered her senior year of high school, not having a boyfriend was something that she wasn?t prepared to accept.

That?s where I came in.

I was a year younger but popular enough to pull off being her boyfriend without too much drama.

I also think she realized that she?d be going away to university the next year and she didn?t want to seriously invest in any kind of relationships back home so that she could broaden her horizons when she left town.

Basically, Stacey was a lesbian.

She knew it, I came to suspect it, and nobody else had any idea in the late 80?s and early 90?s that attractive teenage girls might like other girls.

A couple of years later I found out from her younger sister that Stacey was ?living with? (in the biblical sense) a ?female friend?.

I was nothing more than an accessory for Stacey to keep up appearances and to be honest, I didn?t care much.

Odd Teenage Relationship

I found Stacey hot, but she was a bit frigid when we were alone together. She might allow a bit of kissing, on one or two occasions I may have got to feel her breasts, but that was it.

This was a bit odd for me because I was sexually active from the age of 15, and despite my lack of forward progress with Stacey, it didn?t bother me too much.

The reason? I really liked her family.

It?s true.

She had an older sister that I knew through mutual friends who was really good fun and her younger sister was someone I knew well from school and she was very gregarious.

To be honest, Stacey?s sisters were not great lookers and weren?t blessed with her natural physical attributes, but they were good fun to hang out with.

Her dad had three daughters and a wife, so when I started hanging around their house more, I became like an adopted son.

I remember one time, he asked me very quietly, ?Can we go play catch? I?ve never had a son to do that with and I?d like to do it just one time!?

We went to baseball games and played golf together every couple of weeks, even after she and I broke up.

Stacey?s mom, Jen, was the Alpha of the family, without question.

Whereas her sisters looked like their father, Stacey looked very much like a younger version of her mother.

I think she knew Stacey was into girls, so I wasn?t much of a threat to get her daughter pregnant or anything like that, so was happy to have me around.

Her family became the best part of our relationship.

All Things Must End? Sort of.

After senior prom, Stacey selected the university she would go to and was getting prepared for her graduation.

One Saturday afternoon she asked me to meet her at Olive Garden for lunch and while munching on breadsticks, she told me it was over between us.

I seriously think she did the deed in a public place so that I wouldn?t make a scene or some such nonsense. She made all the usual speeches like, ?It?s me, not you? and ?We?re headed in different directions.?

The truth was, I didn?t mind at all ? I was getting frustrated with her after about six months of just the occasional trip to second base.

I ordered lasagna and asked when she was moving to university.

Later that night, I was sitting at home watching playoff hockey with my dad when the phone rang, it was Stacey?s dad and he wanted to check in on me.

?I?m good Larry, seriously. She?s moving away and I?m starting senior year, it makes sense, she and I were really just good friends anyway.?

Then Larry asked if I still wanted to play golf that coming weekend.

In fact, over the next day or two, both of her sisters called me to say that she was crazy for breaking up with me and Larry called again to see if I wanted to go baseball game with him later that week.

Over the next couple of months during that summer, I don?t think I spent any less time at Stacey?s house than I did when we were going out.

My parents thought that was kind of weird, but joked that I?d been adopted by a richer, cooler family, so good for me.

This Is Where Things Get Weird

As summer turned into autumn, I needed to play less sports and get a job to be able to afford to go away to university. My family just couldn?t afford it and student loans were going to be tough for me to qualify for.

I needed a part-time job and when I mentioned it to Larry, he said, ?Jen?s business is opening an evening shift, I?ll ask her about hiring you!?

Within three hours, Jen had called me at home, offered me as many hours as I could work and a pretty decent hourly rate.

Jen ran a small manufacturing business. These companies don?t exist anymore because everything has been outsourced to China, but back then, these small companies would employ a dozen local people.

My job was to come in after the day shift ended, move the finished goods to the loading area, pull the supplies out of the holding area, and get everything ready so when the day shift came in the next morning, they could start work right away.

I worked every evening from 5pm until 9pm, five days a week and half days on Saturday.

Most days, Jen would let me in and then swing by at 9pm to lock up and drive me home, but occasionally she would stay back and work.

We?d order pizza, chat and I?d do my work.

More and more, she would stay back? She didn?t seem happy.

Crossing The Line You Didn?t Know Existed

One night, Jen came back to lock up, she?d been crying or something and she offered me a ride home.

As we got in the car, she asked me if I wanted to grab a bite to eat before heading home. This wasn?t unusual, if I said I was hungry she?d usually offer to swing by a drive-thru or something.

We pulled into McDonald?s, went through the drive-thru, she ordered herself a meal (which was unusual) and then drove back to the factory and parked the car.

We sat in silence, eating our meals in the darkness.

I asked her if everything was ok and she just started crying.

Normal 18-year-old boys aren?t usually emotionally equipped to handle this, but I was starting to understand my gift of being a great listener and asking poignant questions when I was talking to women. My superpower wasn?t fully developed yet, but I was pretty well advanced.

That night, she told me that the business was struggling, she and Larry were ?just friends? and that she felt like she was alone in the world.

We talked until almost midnight and I never once re-assured her or encouraged her, I just listened, empathized and asked questions to help understand what she was going through.

When she dropped me off at home, she leaned over, kissed me on the cheek and said thanks for listening.

The thing was, the kiss on the cheek lasted that one or two seconds longer than it should have under normal circumstances ?we both knew it.

A line had been crossed? the first of many.

Escalations Happen Faster Than Expected Sometimes

This is where I have to make the disclaimer that this could start to sound like some ridiculous 1970?s or 80?s ?Penthouse Letters? thing, but I assure you, it isn?t ? this actually occurred.

You?ve been warned.

The next night, I turned up for work at the usual time and went about moving the pallettes around as I normally did.

Jen went home but she came back a bit earlier than usual because she?d said she had some paperwork to catch up on. She sat in her office working, while I finished everything off.

When I was done, I swung by her office and told her I was finished and would be heading home.

She offered to give me a lift, but she had another fifteen minutes of work to do before she could leave.

I thanked her, took a seat on the couch in her office and stared quietly at the ceiling.

Before long she swivelled around in her chair to look at me and thanked me for listening to her the previous evening, she just needed to vent.

I told her that I understood and recognized that she was under a great deal of pressure with everything going on.

She agreed and started telling me about some issues she was having in the business. She clearly didn?t have anyone to talk to, so I listened and before long she came over to sit on the couch with me.

She spent the better part of an hour explaining how one of her downstream suppliers had gone broke and the new owners had changed her credit terms which put her at risk.

I was very interested in finance and was going to university the next year to do business studies and economics, so I made a few comments and offered ideas along the way which she seemed interested in.

Then out of the blue, she leaned in and kissed me.

On the lips? open mouth?

A proper adult kiss from an attractive, older woman.

My heart was racing and as she pulled back, she looked into my eyes with a look of, ?Oh, that may not have been the right thing to do.?

I leaned forward right away and returned her kiss? She reciprocated.

Take Your Swings When You Get Your Pitch

Very quickly, the kissing escalated to clothes being removed and hands wandering.

It?s entirely true, no young man knows how to remove a woman?s bra ? I fumbled with this for a good thirty seconds before she reached back and unsnapped the clasps.

I?ll never forget seeing those beautiful, milky white breasts come out with their erect nipples and broad areolas. I had never seen such picture-perfect breasts to that point in my life.

She pulled me into suckle on the nipples and gasped as I took them into my mouth.

I managed to slide my hand down inside her unbuttoned pants and underwear to find her wetness waiting for me.

My fingers traced her damp labia, slid into her gently as she gasped, then I withdrew them to work over her clit using her wetness as a lubricant.

I was on top of her, kissing her hard and pleasuring her with my hand when I felt her first wave of orgasm arrive.

Her eyes rolled back in her head, she stopped kissing me and moaned in a deep guttural way ? her orgasm just kept rolling over her.

As it subsided, I removed my hand and began to remove her pants and panties as she laid on the couch.

I think she thought I was going to mount her then, but I got down on my knees and started licking her out.

The taste was incredible ? that mix of salty, tangy and hints of sweetness.

She had fully grown pubic hair as excessive trimming wasn?t really a thing in the early 90?s and the fully waxed days were some time away.

Her whole body arched as I sucked her pussy, played with her clit in my mouth and probed inside her with my tongue.

I wrapped my arms around her legs and forced my face deep into her ? wave after wave of rolling orgasms came for her.

I loved the increased wetness and lapped it up greedily.

She reached down, grabbed me by the hair, pulled me up and said breathlessly, ?Fuck me, now!?

I dropped my pants moved in between her legs and entered her.

It felt so amazing to slide inside her ? as a young person growing up in that era, we had a very high rate of condom usage because of the HIV scare, but being inside her bareback felt unreal.

Odd Sexual Dysfunction

When I was young, I had a mild sexual dysfunction ? I had what is called ?impaired ejaculation?.

At the time, I had no idea what it was or what it was called, I just knew that about 75% of the time I could get an erection, but couldn?t cum.

I didn?t go soft or anything, it just didn?t happen.

Teenage girls struggled with this because they thought it was them and that I didn?t find them attractive or they were doing it wrong.

Condoms made it worse because they reduced the sensation.

With Jen, I wasn?t thinking about it, I was just fucking her.

She kept telling me to go hard and fast, don?t stop, keep going? so I did.

She came again.

I?d never been inside a woman when she had an orgasm, it was intense and I went harder and faster.

After her orgasm subsided, she said, ?Cum for me.?

I lost control and my thrusting became frantic and intense, and then suddenly it happened? Wave after wave of cum filled her as I leaned back feeling the intensity of my orgasm.

But I was still a young man and I don?t think she was ready for what happened next.

I didn?t stop. I didn?t go soft. There was no refractory period.

I just kept fucking.

Jen was clearly turned on by this as she was now encouraging me to keep fucking her? harder? faster?

She came a few times, but I was transfixed on what I was doing.

Finally, I unloaded inside her for a second time.

I had never cum inside a woman bareback before and it was exhilarating.

The Immediate Aftermath

We sat there collecting our breath? An 18-year-old young man who?d just had the best sex of his life, and then Jen said, ?I?ve never had sex like that before, it was like an out of body experience.?

We just stared forward for a couple of minutes and then I looked over at her and she was smiling, I hadn?t seen that in a while.

I have to admit, I was half expecting her to come to some kind of realization that she?d made a mistake, but she didn?t.

We talked like normal people.

I told her that it was the first time I?d ever finished inside of a woman and that it felt incredible.

She told me that she?d had her tubes tied a few years earlier, so it was perfectly safe and not to worry.

I found out that Larry had not had sex with his wife in over two years and that Jen felt neglected on top of everything else she was going through.

In truth, I think her sexless marriage was probably a big part of what was wrong in her life.

We just sat there naked, talking for the better part of an hour before she gave me a lift home.

Enjoying Our Time Together

Jen and I never really talked about our relationship.

We liked being in each other?s company and we had spectacular sex that benefitted both of us.

Over the next nine months, while I continued to work part-time for her before heading off to school the following year, we would make use of the couch in her office or on occasion in the back of her car if we were feeling like taking a risk.

Jen became a much happier person during that time ? she said I made her feel sexy and desired again.

Her business also turned a corner and she ended up selling it a couple of years later to the downstream supplier who?d been giving her troubles.

I became a much better lover thanks to Jen.

She taught me to slow down a bit, breathe deeply and feel what was going on more. She taught me to close my eyes during sex so that I could listen to my body more.

After a couple of months, my impaired ejaculation abated. I found out later that Jen?s advice and our regular sex worked to teach me how to orgasm in a proper fashion.

I stopped hanging out with Larry and going to their house ? it felt weird as you might imagine.

I?m not someone that feels ?guilty?, I never really have been, I guess I?m a sociopath like that, but I was worried it would make Jen uncomfortable.

We never really talked about her family either, although one evening, I asked her how Stacey was doing at school and she asked me if we?d ever had sex. I laughed openly and told her that I may have touched her breast once or twice, but that Stacey wasn?t really that into me.

Jen smiled at hearing that. I think somewhere inside, it made her feel better about what we were doing.

All Good Things Come To An End

As the time came for me to go to university, my last day at work became apparent and there was some level of awkwardness between Jen and myself.

We would have sex still, but it felt less ?hopeful? and more? sad.

Sad isn?t maybe the right word, but it?s the best that I can think of ? we knew time was coming to a close on what we had, so I think we both felt a bit bad about it ending.

One of my last evenings of work, we sat on the couch, post-coitus, and Jen said to me, ?This has been fun, but when you move, we both need to move on with our lives, no looking back.?

I told her that I?d be coming home regularly to visit family, so we could catch up or whatever, but she cut me off.

?I would like that, probably more than I care to admit, but it?s best if we just call it a day on this.?

I was disappointed, the sex was terrific and she was great, but I knew she was right and it was the smart thing to do.

I bumped into her every now and again when I would be back home for a visit, or in the summer. We?d talk like old friends and laugh, but a quick hug was as far it would go.

A few years later after Jen sold the business, I found out from Stacey?s younger sister that her parents had broken up.

Larry had been having an affair for nearly ten years with a woman from the golf club he belonged to and they were now living together.

Jen had been single for a while, but she met a guy about ten years younger than her and they?d moved Florida together.

I told Stacey?s younger sister to say ?Hi? to her mom for me the next time she spoke with her and she told me that her mom always said what a great young man I was.

Funnily enough, Jen and I became friends on Facebook just last year when she sent me a friend request after she noticed I was friends with Stacey and her other two daughters.

Shortly thereafter, Jen pinged me on Messenger to ask how I was doing, asked about my life and we talked about what we?d each been up to over the years.

She ended the conversation with, ?I think about you from time to time, we had good times together.?

I replied, ?I think about you a lot and how great that year was.?

Author?s note: Names and places changed to protect everyone?s privacy.

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