My name is Andrew and this is the night that changed my life forever.  This single event directly involved my best friend, Jennifer, whom I have been the closest of friends for the last thirty-plus years.   I met her many years ago while in college.  Between classes, several of us would meet in a common area.  One random winter day, I decided to excuse myself from our group of misfits, step out, and get something to eat.  Strangely enough, fast food was in order.  One can only hope that my digestive system would forgive me.

Out of nowhere, a young lady, nineteen years of age and whom I had never seen before, approached me.  She introduced herself and inquired if she could join me.  I must admit, I was rather surprised, but who was I to say no.  She just came from a dance class and she was wearing a rather shapely dance outfit.  Still, it was in good taste, acceptable for class, and pleasant to look at.

It was a frigid ten degrees outside, so we moved across the parking lot swiftly.  We climbed into my beet up old station wagon and drove off.  I thought it was rather odd that a young lady was trusting enough to invite herself to accompany a complete stranger in his vehicle.  Jennifer was in no danger.  Somehow, she was quite certain that I was no threat to her.

I knew I liked her very much from the moment of her other-than-standard self-introduction. Jennifer was a little nervous and talked continuously.  I found her fun and amusing.  Actually, I enjoyed her company and conversation very much.  She then said that someone back in the college hallway walked past her and made a dumb comment, “nice tits.”

I was a little shocked that she just blurted that out.  However, she was very interesting and intriguing.  I just listened.  When she made this comment, the horns on my head popped out.  I almost told her, “Since you are talking about them (breasts), are you going to show them to me?”  Luckily, common sense had prevailed.  Somehow, I knew deep inside that it was imperative to be a gentleman and refrain from that comment.  Furthermore, I may have frightened her.  Since I felt a connection and liked her immediately, I elected to just smile and say nothing.

Jennifer and I quickly became the best of friends.  We loved being in the same room together.  We found each other captivating and we would talk for hours.  Not long after, we would be having sexual relations.  It was the proverbial “Friends with Benefits.”  We took care of each other’s needs when either of our desires dictated.

At that time, I was an aspiring pilot with my whole career in front of me.  My main focus was my education and my career.  Nothing could stand in the way.  Jennifer on the other hand, wanted a family.  We always remained the closest of friends and we stayed in contact with each other.  We eventually married other people and carried out our soon to be miserable lives regarding our poor choices in spouses.

I never realized how much I missed and cared for Jennifer.  She was always my best friend.  She always, without question, was in my corner offering her support.  Conversely, I always offered mine as well.

Our separate lives droned on and on for many years.  Our friendship provided us with the grounding, clarity, and stabilization needed for our emotional survival.  This deep, trusted friendship never impeded nor interfered with our marriages.

Eventually, somehow, we began exchanging illicit digital photos of ourselves.  These photos were sanitized by never revealing faces or other identifying characteristics.  It was fun and exhilarating.  It brought back the excitement that was missing in our lives.  We had one rule.  The rule was to never touch each other inappropriately, in other words, safe enough for our spouses to witness.  We adhered to this rule with conviction.  Always!

Over the years, it was quite apparent that I missed Jennifer terribly.  I often contemplated what it would have been like to be with her.  However, I knew this was not possible, so I never entertained that notion, much less tested the waters.

Many years later, I spoke to Jennifer on the phone, as I often did.  I told her that I made arrangements to be in Northern Ohio to visit my family, and I would like to see her too.  She said that would be great and would like to see me as well.

As usual, we then transitioned into talking a bit dirty and the conversation led from one thing to another.  Since I really was a shy person regarding sex, I feebly attempted humor in a sexual fashion.  Without thinking, I slipped out a joke alluding to the fact that I wish I could take one photo of her personally, or at least see her naked body again.

This was all followed by a very uncomfortable pause with an awkward silence.  Oh no!  How did that sneak out?  I’ve really done it this time!  My mind is now racing at an unimaginable level while I feel like my heart had stopped in its tracks.  That was it, I resignedly felt like I had stepped in shit and it stuck to my shoes, but this time I tracked it across the living room carpet (figuratively speaking, of course).

Jennifer was the first to speak and said sweetly, “You want a photo shoot?”

I sheepishly said, “Uh…uh…yes.”  I then quickly clammed up and said nothing.

Jennifer softly giggled and responded with, “I’ll mull it over.”

The most intelligent thing I could think to say was, “ok.”  I did not know what else to say, so I changed the subject.  I had no idea what, or if anything would transpire.

Then it dawned on me.  The last thing I ever wanted to do is remind her of that ignorant horse’s ass she was still married to.  I felt stupid.  There I was, possibly making her re-live several miserable events from her soon-to-be married past.  What in the hell was I thinking?

One week later:

It was a sunny afternoon in Northern Ohio.   I arrived safe and sound after a two-day drive from deep in the Heart of Texas.  It was July 27th, in the year 2021.  Yes, 7/27, a number that will forever be etched into my memory.  I checked into my hotel suite early enough to rest and take a shower.

It was 5:00pm, and I was waiting anxiously.  Normally, I would be able to hide behind my pseudo imperturbable demeanor.  The truth is, I felt as nervous as a dog shitting peach seeds.  I couldn’t wait to see her, Jennifer, my closest friend of thirty-five years.  Besides everything else, visiting with my friend, whom I could discuss any topic or personal situation, was paramount.

Still, I could not stop thinking about the intimate thrill of maybe, hopefully, seeing her naked.  It was always an erotic thrill when she sent me special photos of herself.  Even after all these years, I still fantasized about seeing her naked.

Jennifer said that she lost a lot of weight.  I wanted desperately to see her in person without clothing, and maybe I could snap a quick photo.  So, I figured that this would be a viable excuse to accomplish my lustful aspirations.  A quick look at her beautiful breasts would suffice.  Anything from her would be very exciting to me.  Just a quick view may have been all one could hope for.  If I could be that lucky, another fantasy would be fulfilled.

Wait!  What was I thinking!?  I felt like such a scumbag.  So, if this topic came up again, I will just be direct with by beautiful friend and accept any answers she gives me, without question.

We had been occasionally sending digital photos of ourselves to each other for years.  Selfies were always ok with Jennifer, probably because her asshole husband was not involved.  Her pics turned me on like no other.  She was the only person who I shared with.  Conversely, I was the only person she shared with as well.  The pics were always sanitized by refraining from revealing faces or other identifiable features.  Still, today could be different.  If I were lucky enough, I may be blessed with just a quick look, or photo, in person.

If this is at all possible, it would be a very far stretch.  This would be resembling the stars lining up for me, which I did not expect.  Maybe I would be blessed with that gift.  The gift would be “me” being granted the coveted luxury of taking a photo of her showing her beautiful breasts.

For the next hour and a half, my heart was pounding, and I was unable to relax.  I still had no idea what to expect.  I’m in a quandary.  How does one ask for such things?  How does one have the audacity to think this may happen?  Then again, Jennifer is my closest friend, and we have been involved in the distant past.  We were friends with benefits and we could discuss anything.

We had exchanged forbidden fruit (elicit digital photos) for years.  However, I still can never forget that Jennifer is a living and breathing human being with feelings.  My dearest friend is not a toy or something to be used and discarded.  On the other hand, she is the one who turns me on to the point where I tremble.  And still, I have no answers.

It is now 6:30pm and there is a knock on my door.  It’s her!  It is definitely her!  My friend, my fantasy, my drive and feelings that I cannot explain, much less understand. What is happening to me?  I do not comprehend!

Nevertheless, there was nothing in this world that was going to prevent me from opening that door.  There she was. Jennifer.  My favorite person.  I looked deeply into her eyes, those beautiful grey eyes.   They were absolutely magnificent.  As usual, I was captivated.  After a long gaze, I sincerely hoped that I had not been exposed.  Her smile was warm and sincere.  We embraced, and we were wrapped in each other’s arms.  We were holding tightly, as if we would never let each other go.

I kissed her on the cheek and I kissed her again.  Then without cognitive thought, I committed the unthinkable.  I held her cheeks and kissed her straight on the lips.  Jennifer was caught off guard and pulled back a little.  I recovered gracefully by kissing her on the cheek again and played it off like this was no big deal.  I acted like I was only happy to see my closest friend, because I was.  By the grace of God, I dodged a bullet.  I then invited her into my suite and we began talking like we always have in years past.  We sat down and tried to catch up.

To my dismay, Jennifer appeared to be nervous.  This made me nervous as well.  Nervousness was in the air and contagious.  Jennifer looked at me and said, “Let’s have dinner.”  I wisely agreed.

Upon our return, we entered my suite again and were much more relaxed.  We conversed like we always had.  She is my friend, my beautiful best friend, my favorite person.

I pulled up my laptop and said, “As I promised a few days ago, I have something for you.”  Maybe Jennifer thought I forgot, or I changed my mind.  I didn’t.  I inserted a flash drive into the USB port.  She was focused on the screen.  She had a faint smile and her eyes glowed like a beacon in the night.

When we talked on the phone before I began my journey to see her, we were having a very dirty and intriguing conversation.  I told her she could have all of the elicit digital self-photos of me.  Why not?  They were all taken with the intent to give them to her anyway, somehow, someday. 

She stated she wanted them.  The difference was, they were completely unedited.  Yes, you guessed it, full frontal and facial exposure.  I joked about making a couple of unedited videos.  These videos contained masturbation followed by ejaculation.  She did say she wanted to watch me lose my load.  So, I willingly obliged.

This is completely out of character for me.  I’m the kind of person that would not admit to anyone that I would occasionally masturbate.  However, I always admitted this to Jennifer.  Moreover, she always admitted to me that she masturbated as well.

Jennifer is my best friend and I trust her implicitly.  So, I willingly agreed to provide her with the said digital entertainment.  Obviously, over the years, she had provided several photos and videos of herself to me.  However, we had not crossed that barrier of full-frontal nudity with facial exposure.  Consequently, I took the risk and moved first.

While showing Jennifer everything on the flash drive, she became more relaxed and appeared to feel safe.  She knew we both agreed and understood this needed to be this way.  We had one simple rule: do not touch each other inappropriately.  This meant that we could not fondle each other or have sex.  I then removed the flash drive and gave it to her.  She was grinning like the canary who ate the cat this time.

Jennifer reached into her bag and pulled out a slightly see through net body suit.  It had a release on the crotch.  She asked me if I minded the bodysuit, and if I minded that she shaved her pussy.  I smiled and said the body suit and shaved pussy is extremely erotic.  I asked her if she had any idea what this is doing to me.  I told her I was as hard as a rock.  I then asked her, “Do you want to see?”

She smiled and said, “Yes, of course”.

I was wearing dressy shorts that had a lot of room.  While sitting on the living room chair, I turned towards her and leaned back slightly.  I spread my legs apart and slid my hard penis out of the left leg.  She smugly looked, smiled, and said, “Very nice.” 

Of course, I replied with, “Thank you.”

Jennifer promptly stood up with her head held high.  She briskly walked to the restroom with her body suit in hand.  She walked with a level of confidence I have never seen before from her.  I must admit I was a little intimidated, but also very impressed.  My penis became very hard again from the thought of what I may see.

Jennifer emerged from the restroom of the suite.  She approached me and asked, “What do you think?”

I told her, “I love it!”  I then showed her my pulsing rock-hard penis again by sliding it out of the left leg of my shorts while clutching it in my left hand.

As I was sitting on the living room chair, Jennifer sat on the couch directly in front of me.  She leaned back into the corner of the couch, with her right knee bent, and against the back.  She then spread her legs apart and moved her left leg, with a slightly bent knee, to the edge of the couch.  With a smile, she unhooked the crotch of her bodysuit and lifted it up above her stomach.

There she was, laying back diagonally on the couch with her legs spread apart displaying her beautiful pussy.  It was the most erotic sight I had ever seen.  I am two to three feet away from her.  I am looking at her while she was wearing her partial see-through body suit with her pussy totally spread and exposed.

My penis was so hard and it was throbbing incessantly.  I don’t believe it has ever been that rigid.  Then the impossible happened.  I was granted permission to photograph her body to include her face and her beautiful pussy.

I was vigorously trembling and having a difficult time holding my phone still.  Logic prevailed, and I immediately composed myself which allowed me to capture many beautiful images.  This was absolutely amazing!  I actually got to take photos of her showing her pussy to me.  I was earlier considering myself blessed if I could just take a quick peek at her breasts.  Forget the little peek. I am actually photographing her pussy without her hiding her face.  My sexual fantasies were coming to fruition before my very eyes and my penis was hard enough to explode!

Jennifer then began gently, smoothly, and seductively caressing her pussy by rubbing it with one, then two, then three of her fingers.  She inserted her middle finger and moved it in and out.  Then, her ring finger was slid in and out of her vagina as well.  She rammed both her middle and ring fingers as deep inside as she could while moving them in, out, and all around.  She drove her fingers in as deep as her last knuckles.  This was incredible!  I continued to photograph and take a few more videos.  More of by buried and sequestered sexual fantasies were coming true.

I had a small two AA-battery flashlight sitting on the side table with my wallet, keys, and other travel accouterments.  She acknowledged the flashlight and asked, “What is this for”?  In my shyness, I resorted to a feeble attempt of humor again.  I said it was for inspections when I was working.  I was now holding it and jokingly asked her if she would like an inspection.  Actually, there was a small part of me that was not joking.  She smiled and said we can’t.  I completely agreed.  Jennifer then took my flashlight out of my hand and illuminated it.  She inserted the flashlight up into her pussy.  She moved it in and out while it was slightly lighting up the entrance of her vagina.  I photographed and videoed more.  I could not believe my eyes and I was speechless.  At this time, I considered myself the luckiest man that had ever walked the face of the earth.

Then, all of a sudden, out of nowhere, I remembered a previous conversation that she liked ice.  At the risk of sounding like a deviant (due to bad programing from my soon-to-be ex-wife) I asked her if she would like some.  She responded favorably.  I said, “Really?” 

She smiled and said, “Yes.”  I handed her a tall glass of ice.

Due to the promise that we made to each other, I knew I would not be able to participate or assist in the insertion of the ice cubes.  I wanted nothing more but to take each elongated ice cube and gently insert them into her vagina myself.  I couldn’t.  I would lose my honor and her trust.  Damn!  So, I continued to photograph and video her naked body while she inserted the ice cubes, one-by-one, into her longing and wanting wet pussy.  It was a sight to behold.

By happenstance, I glanced at the counter and noticed there were a few bananas left over from my road trip.  They were still a little green, which ensured their firmness.  At this point, I was losing so many of my personal barriers due to shyness.  I began to develop many dirty little ideas that were derived from pure fantasy and lust.  I was salivating over the notion of gently sliding one of those bananas up inside of her vagina.

Jennifer is my closest friend and I do not feel that she would judge or think less of me.  So, I asked her if she would like a banana.  She smiled again and said, “Yes.” 

I must have resembled a young child that excitedly said, “Really?!”

She again said, “Yes.”  Understanding that I could not insert the banana into her vagina myself, I handed it to her.  She put that banana up into her pussy and slid it in and out.  She shoved it all the way up inside of her again.  Luckily for her, it was not a large banana.  I remember that she always had a rather tight pussy.

While the banana was as far up inside of her as possible, it looked as if it had disappeared.  She then slowly pulled it out.  She continued to move it in and out and all around.  I was so hard and excited that I was amazed that I didn’t lose my load and cum all over myself.  Once again, I was able to photograph and video this sultry view of her ramming a banana into her pussy.  I began to feel that this could not be real because I have never experienced this level of erotica in my life.  This was the ultimate “maximus-penis-erectus!”  She could have dragged me around by my dick and I wouldn’t have cared.  I was hers!

I reached for the flashlight off of the coffee table.  Ten minutes ago, it was inside of her.  I wanted to know what it smelled and tasted like.  I was distraught for a moment because she got to the flashlight first and had licked the vaginal secretion off of it herself.  After all these years, I still did not know what she smelled or tasted like.  Damn!

Consequently, I quietly and smoothly sniffed the banana and licked her juices off of it.  Unfortunately, all it tasted like was a banana.  If I could, I would have slid my tongue deep inside of her.  I wanted to taste her pussy and lick her juices.  Denied.  Damn!

Jennifer was very excited about these events and asked me if I wanted to see anything else.  I drew a blank.  I couldn’t think.  So, at the last second, I asked for a photo of her laying on the couch spreading her pussy.  No insertions, just that incredible and beautiful spread pussy.  I took the photo, got closer, and took more.  My face was a foot and a half away from her.  Closer…I wanted to get closer.  I only wanted to know what she smelled and tasted like.

In the past, I was only able to gleam a slight hint of residual secretions from our sexual encounters.  Although the evidence was minimal, the indication was favorable. My inquiring mind needed to know.

I wanted to ask her to take the rest of her body suit off, rendering her completely naked.  I would have liked to photograph her lying on the bed with her legs spread apart, her knees bent, and her feet flat on the mattress.  This would resemble the “I want you to stick it in me” look.  I fully understood that we could not have sex.  The photo would have gotten me off time and time again.  However, I didn’t think that would make her feel safe, so I kept it to myself and did not enter that domain.

While still on the couch, Jennifer pulled her pussy apart further.  At my request, she put one finger from each hand deep inside.  Then she gently spread her lips and vaginal entrance.  I was able to view the inside of her vagina.  This was the most spectacular event I have ever witnessed, much less photographed.  She trusted me implicitly.

It was now my turn to pass on the favor to her.  She covered up while I removed my shorts.  My rock-hard cock stuck out like a spear.  While right in front of Jennifer, I stroked my penis until I was ready to ejaculate.  Jennifer laid down on the couch so I could cum in her mouth without her sucking it.  I came so hard it was like the fountain of youth.  She collected my seed on her tongue and in her mouth.  Jennifer cheated a slight bit by sticking the tip of her tongue into the hole of the head of my penis.  Still, she did not suck it.  She then swallowed the rest of my load.

I then sat down and we relaxed while basking in the afterglow of our most erotic adventure yet.  The time was slipping by and it was getting late.  To my dismay, Jennifer needed to leave.  I walked her to her vehicle.  After exiting my suite, she took my hand and walked with me.  Her touch was electric.  What was this all about?  We never held hands or held each other before.

At first, I experienced a very strange repelling feeling, probably similar to Jennefer’s reaction to me kissing her on the lips.  I immediately was taken back.  However, after about two seconds, I felt very comfortable and warm inside.

Then all of these feelings were followed by an accentuated burning desire for Jennifer.  This was not just the need to get up inside of her. Instead, I actually wanted to take her in my arms, hold her close, and kiss her passionately.  This was some anomaly that I could not identify and was increasing exponentially inside of me.

We hugged each other strongly and kissed each other on the cheek several times.  I wanted more, so much more.  The following morning was like being pounded by Thor’s hammer, which led to an unimaginable rearrangement of my entire life.  That is a continuation of this story and it will follow soon.

We both were at the ending stages of very bad marriages.  During those twenty-plus years, we never touched each other inappropriately.  However, one may conclude that what did happen was inappropriate.  Maybe it was.  Maybe it maintained our sanity.

My beautiful closest friend, Jennifer, is now my wife.  She has been the love of my life for over thirty years.  We finally realized our feelings and moved forward into the next stages of our lives.  We are blissfully happy and have two children.

I hope you have enjoyed reading this story.  The names have been changed to protect the Guilty as Charged.  I can only hope that no one is quick to judge.  There are so many other facets to this story and if I told you everything, you may not believe me.