Friends With Benefits

It's been almost a year since I wrote my last story; here is a new situation that is about three months in the making.  If anyone has any thoughts on this, please feel free to share.

By the way, the woman who was central to my story entitled, "An Affair To Remember" is out of the picture.  She ended up being very clingy and very prone to wanting to argue with me over texts.  I ended it and she was very upset about it; she moved on with someone else.

This past summer, I reconnected on social media with a female friend ("S" for the sake of this story) whom I have not seen for a long time.  S is in her early fifties; I am a few years older.  For my own reasons, I am not going to say how long S and I have been friends.  At any rate, we caught up initially on texts and later by phone.  She and her husband live within driving distance.

She initially suggested that we get together for dinner at some point, going as far as to call it "a date".  I was kind of taken by surprise and when I asked if her husband would mind, she essentially told me that she has a "hall pass"; he does not have the same because she wants it to be a one-way street.  She has very limited experience with this, and it has been a long time since she did it.  I have zero experience with open relationships and "hall passes" and she is well aware of it.

At the end of one of our calls one evening, S told me as we were ending the call, "I love you."  I was shocked to hear it, but I told her that I loved her back; as a friend, although I knew that this had the propensity for more.

At the time that this discussion took place, I was (and still am) with my girlfriend ("L") who is in her early sixties.  We have been arguing for almost a year.  The arguing ranges from topics such as how I am raising my kids as a widower to her low sex drive because of a variety of reasons.  My girlfriend and I live separately.  

Right before I planned to meet S at my hotel when I was near where she worked, my girlfriend and I had it out so badly that I was seriously considering ending the relationship.  

I arrived and got my work responsibilities done.  I checked into my hotel and later that day, S and I reunited after many years.  Again, we have always been just platonic friends.  I met her in the parking lot and we hugged and then we kissed.  It was only slightly awkward.

We went up to my room and I made drinks for us.  We decided to hit the pool since the weather was so nice.  We talked and drank and embraced in the pool.  We kissed each other many times and I held her body and she did the same to me.  

After a while, we left the pool and went to my room to change clothes and to go to dinner.  We drove and talked some more.  Dinner was excellent; I paid up and we went back to my hotel room.

Once there, our clothes came off.  When we were naked and in bed, I went down on her first.  Her tight pussy was warm and slick with her juices; I ate her hungrily as she moaned and moved under me.  She then went to work on me with her mouth and she gives excellent head.  My cock was leaking and I was on the verge of an orgasm with the magic that she had within her in that moment.  She rolled her tongue over and around my glans and shivers went down my spine.  To say that her skills are great would be an understatement.

I wanted to taste her again and flipped her onto her back and burrowed my tongue in and around the soft, pink folds of beautiful labia; she tastes so good!  I alternated on slurping on her, fingering her and massaging her nipples and feeling her perfect and very large breasts.

Her asshole was dimly illuminated in the room and I ate her ass with no reservations.  Like her pussy, it also tasted amazing.  I worked to push her over the edge.  At some point, she flipped over as I drove myself deep into her very wet and tight pussy while grabbing her hips and ass.  I also took her nipples between my thumbs and the tips of my forefingers as I licked and sucked her wet cunt.  We ended up in missionary and I felt like my energy was infinite as I continued to fuck her.

On a particular thrust, I knew I was there.  About seven or eight more pumps and almost a week of cum shot into her womb as I continued thrusting into her, feeling the heat of her insides.  I savored the moment, staying inside of her and pulsating. 

We kissed quite a bit post-orgasm and we got dressed; she needed to go home.  

I walked her downstairs.  We kissed some more.  We said our goodbyes and she started her car and left with my load still in her.  I checked in to make sure she made it home safely.  She later told me that when she got home, she and her husband had awesome sex.

A few days went by and my girlfriend "L" asked me to come over to her place one morning because she was not feeling well.  We were still not in a good place, from a relationship standpoint, but I felt that it was right to be there for her.  When I arrived, she cried because she missed me and in so many words, she was regretful of pushing me away.  I sat on her bed and she embraced me and we kissed passionately.  We got naked and had the best sex that we had in years!  My stamina is such that I can usually have sex for sometimes nearly an hour and just enjoy the ride before I have an orgasm.  This time, I came within about ten minutes.

Things between L and I got better after I fucked her like it was the end (we both had the same thought).  This was the case for several weeks until that all faded and then we went back to the usual, which was unfortunate.

A few weeks went by and S reached out to me again, asking about setting up another rendezvous.  I agreed and plans were made.  We set things into place.  I let L know that I needed to be out of town again ("for work"); she eventually was skeptical and even asked me if I was seeing someone else and I brushed it off.  At that point, we were playing the "on and off" game again (not initiated by me) and although I didn't want to lie to L, I wanted to spend time with S again.

For our next session, we once again grabbed dinner and drinks.  We then went back to my hotel room.  We made out intensely, got naked and our hands were all over each other.  We had previously discussed whether or not she liked getting fucked in the ass (she does) although this time we pretty much stayed close to what we did last time with the exception of us being locked in a hot 69.  My tongue was soon buried in her pussy and she blew me like a fucking porn star.

I flipped her onto her back and ate her pussy; this time, she had a shaking orgasm as my mouth and tongue worked on her clit and all around and in her pussy.  I tongue fucked her and heard her breath get raspy.  She came and as she did, she grabbed the sheets and my hair and pulled my face even tighter into her.  When her orgasm subsided, she kissed me and licked her juices off my face.

My dick was so hard at that point and I moved up and into her pussy which felt like I was plunging into hot lava; it felt amazing.  I was so turned on and it wasn't long before I felt my cum rising up.  I wanted to cum in her mouth this time and I got onto my back and she blew me to completion.  My load shot into her mouth and on her face and dripped onto me.  I kissed her afterwards and we got cleaned up.  We kissed some more and she left; once again, to go home to her guy.

I checked out the next day and went home.  L was still leery of me being out of town but that eventually was no longer an issue.  L and I had more sex the week following than we had in a while and it was incredible.

A few days went by and S texted me (or so I thought); her husband actually reached out to me on her phone (with her knowledge).  In so many words, he suggested that I should keep it "light" with S because she isn't very good with deep feelings.  

This hit me hard.  I responded that I understood; however, I could not help but feel that things had changed now.  Perhaps this guy has some level of regret letting his wife be with me; however, although I acted on it, this was NOT my idea.

The next day, S reached out to me on text.  Once I knew that it was in fact her texting me this time, she said that he meant well.  My response was that although he may have meant well, it didn't come across that way.  From my perspective, the entire dynamic of all of this changed dramatically.  She was emphatic in trying to reassure me that there was nothing for me to be concerned about and that she wanted to continue what we had started.  She referenced the fact that she and I had been friends for a long time and that she enjoys this new aspect of our friendship.

Again, all of this is very foreign to me.  It was the first time that I have ever been involved in anything like this.  I have had many relationships and not once did I ever want some other guy to bang a girl with whom I was involved.  Even in my present relationship, when L and I have our moments where we are at odds with each other, I would never want another man to have her.  Although I don't understand all of this, I respect that it is the choice for S and her husband to make.  She and I are very sexually attracted to each other, but I really don't think that this is what I want anymore.  Additionally, I want to work on making my relationship with L a better one.