My Best Worst Conversation

Katy and I had only been together just short of a year after having met each other online. Her living in California and my living in Ohio made the 1st few months pretty difficult as it was a long distance relationship.

Katy at the time was an entrepreneur and I was in between jobs after my father had passed away suddenly. So this adventure time out well for both of us.

We began our meetings by flying to each other's homes and staying there a week at a time, and after we determined our chemistry was significant enough, we worked it out that I would give it a try to come out to California for a 3 month dry run living together full time.

Katy was very appealing to me as she was in her mid 30s with an athletic build as she went biking 10-20 miles a day to stay fit and was an avid golfer. Her competitive spirit drove us both to the brink of insanity because it was never my thing to finish 2nd at anything.

Considering that besides her, I had no other personal connections in California, my social life revolved around her and her circle of friends. This was before the social networking sites were mainstream, so I was pretty much on an island in California of all places.

One of her friends was John who was dating Lauren at the time I met him at first, but later on got dumped because of his obsession with porn. He and Katy had been friends for years as John worked in a law office that Katy had had dealings with and she had never had relations with him and for the friendship decided she never would and he obliged that request.

John was not a fan of mine from the very beginning. Both he and Katy were both college graduates whereas I was not and the fact that Katy was racking in 6 figures made him, and others believe I was a leach that had found a windfall in meeting Katy. This was never more apparent a couple months after our 1st meeting when I heard him tell her that she could do better. I kept my cool and addressed it with Katy after our night out with John and his girlfriend and I never saw John again.

When our dry run period had come to its end in August, after a fun summer of adventure and great sex, reality sunk in. With limited social circles and my inability to find adequate work out in Cali along with other mitigating circumstances, we decided it was not meant to be and I came home to Ohio. During her visits to Ohio, Katy could not reconcile the differences of climates and lifestyles between the 2, so she did not follow me.

As we had done previously before our dry run, we would chat on the computer and talk to each other on the phone and enjoyed some erotic conversations so much to the point we both considered maintaining a friends with benefits relationship and my coming back to visit every so often.

Then both the worst and best conversation of my life took place early on a Saturday morning as my phone rang at 6: 36 am as I will never forget waking up so early and seeing my clock and wondering who is calling so early. It was Katy. And here is the conversation to the best of my recollection:

Me: Hello

Katy: (about 5 seconds of silence) Michael, did I wake you?

Me: What's wrong? Why are you calling so early?

Katy: (more silence) I needed to talk to you. Something happened tonight.

Me: (having realized the 3 hour time difference from our previous conversations, I realized it was still her Friday night vs my Saturday morning even with being woken up as I was) What happened honey?

Katy: Do you remember John?

Me: Yea, the guy who told you that you could do better than me.

Katy: (sighs) Yeah. Well he did something tonight. I can't believe he did it and I...

Me: (choked up) Kate, did you sleep with John?

Katy: NO! NO! NO! I told you I would never sleep with him.

Me: (relieved) Ok, ok. Settle down. (As I could hear her sulking a bit at my accusation) What exactly did he do?

Katy: I am so embarrassed. I can't believe I did this. (sulking all the more)

Me: Did he hurt you Kate? I swear I will be out there as soon as I can and I will take care of John.

Katy: No he didn't hurt me.

Me: Then what? What has gotten you so upset?

Katy: You promise you won't be mad.

Me: Mad about what?

Katy: You have to promise.

Me: OK, I promise.

Katy: You have been gone a month now and I know we have our fun together chatting and talking.....I have missed you so much.

Me: I miss you too baby.

Katy: (sulking a little more) John introduced me to 1 of his lawyer friends tonight when I met him for dinner and he let me drive his BMW.

Me: (realizing she went on a date, I sat up on my bed in a cold chill trying to compose myself)

Katy: Michael, are you still there?

Me: Yeah, I am here

Katy: I am so sorry I called you. This is so not right.

Me: It's ok. I ... I am ok. We are friends and you called your friend no matter what (still in a daze from having just woken up, but fully aware that this was a bad start to my Saturday)

Katy: Are you sure? (sulking) I don't know who to talk to about this and I can't even think about John anymore after what he did to me.

Me: What exactly did John do exactly if he did not fuck you?

Katy: (silence for about 10 seconds)

Me: Katy?

Katy: You promise you will not get mad?

Me: I promise

Katy: He set me up with his lawyer friend who let me drive his BMW back to his place.

Me: OK

Katy: Well, when we got back to his apartment, John was there with another of his lawyer friends, and at 1st, I was relieved because I figured we were just gonna hang out, you know.

Me: (trying to picture the scene she is laying out) Ok

Katy: Then John......

Me: Katy? What did John do?

Katy: He said he wanted to see me do better than you and wanted me to fuck his friends.

Me: (stunned) He what!

Katy: You promised you wouldn't be mad.

Me: (breathing heavier trying to calm myself for her sake) Honey, I don't know what to say here.

Katy: It's ok. I can't believe I called you.

Me: I'm ok. We are not a couple anymore. It would not have been cheating if you had done anything.

Katy: (sighing)

Me: Katy? Did you?

Katy: (hangs up phone)

I pulled up the call log and called her right back and it went to voicemail 3 times as I pleaded for her to call back as the reality sunk in that my beautiful Katy wasn't mine anymore. My mind was racing and although we had not been together for close to a month, it was devastating to me. On my 4th attempt about 25 minutes after she had hung up on me, she picked up.

Katy: (phone picked up with silence on her end)

Me: Katy, please talk to me.

Katy: I don't think I can do this to you Michael.

Me: You let me decide that, ok. We are friends and...well..

Katy: Well what?

Me: (breathing rapidly) Did you fuck them?

Katy: (in a whispering voice even though she was alone) Yes.

Me: (completely dumbfounded beyond belief) Oh my God!

Katy: I am so sorry I did this. I should've never called you.

Me: Give me a minute, ok.

Katy: Ok

(To this day, I cannot believe I took the conversation in the direction that I took it and will never forget the erotic pleasure I got out of it.)

Me: Katy. You called me this morning and you will have to agree I have been super cool under the circumstances.

Katy: You must hate me.

Me: Not at all. We have done the phone sex thing before. This is simply more than phone sex because you just fucked 2 guys. Can we talk about it?

Katy: (coughing) What?!

Me: You called me and you obviously wanted to talk. I just want to talk about your night.

Katy: You sure?

Me: Yes. Tell me everything how it played out and I will try to listen as best I can without interrupting you.

Katy: Ok. Well, when John said that he wanted me to fuck his 2 friends, I laughed and so did they. Then I realized he was serious, and I was in shock. Then the taller 1 said that John had told them I was on the rebound and could use some help.

Me:(sighs)

Katy: Should I stop Michael?

Me: No go on. (lying naked on my bed under the covers cock in hand listening to her story)

Katy: Ok. Well, I screamed at John. I could not believe what was happening. I was in this guy's apartment and my friend had basically set me up not for a date, but a booty call. I felt like such a slut Michael.

Me: (thinking to myself not saying anything-Well you are) Honey, you're not a slut.

Katy: (takes a deep breath) ok. Well after my tantrum, the shorter of the 2 comes over to me and starts massaging my neck and telling me to calm down and that they were in similar situations and they had been recently divorced and John wanted to help all of us.

Me: (interrupting as I promised I wouldn't earlier) Were they white or black? How old were they?

Katy (not pleased at all as I could tell by her tone) They were both white and in their 40s and yes, they were bigger than you.

Me: Ok,ok. Sorry.

Katy: Should I keep going?

Me: Yes. I will not say another word until you ask me to.

Katy: Well I looked at John as he sat in a chair and seemed to be ready to watch a show and then the guy massaging my neck stuck his tongue in my ear and I flinched away from him and looked at him and he wanted me Michael. Then the taller one smacked my ass.

Me: (knowing Katy loves it rough)

Katy: It was a hard slap Michael and I rubbed my ass as I heard John laughing as he said "I told them you like it rough Kate." I backed away and they watched me. It was awkward for a couple of minutes and I thought to myself I am single. What do I have to be ashamed of? You know?

Me: (already stroking my cock) "You are right"

Katy. Thank you for being so cool about this. I never thought talking about this with you would be so easy. Are you enjoying yourself?

Me: Yes

Katy: I'm still sore, but l am enjoying this too (seductive and sultry voice) Well, I looked at John and told him what I thought of him telling him he was an asshole and after tonight that we probably could never be friends again. He stayed silent when the shorter 1...

Me: Don't you know their names?

Katy: (Upset at my interruption I think or simply embarrassed by her upcoming answer) I don't remember their names, ok!

Me: Ok, go on.

Katy: The shorter 1 says to me"Kate, John is a perv. That is for sure. Please accept our apologies on his behalf. " I looked at John with disgust when the taller 1 walked over to me and whispered in my ear "John wants to see you fucked and we definitely want to fuck you." He then backed away basically letting me decide my fate. You still there Michael?

Me: (breathing a bit heavier in my response) Yeah, go on.

Katy: I was certainly ready to leave, but I have missed you so much and these guys wanted me Michael. I don't know what came over me. I walked over to John's chair and asked him point blank "You want me to be fucked by your friends?" He stood up and looked up to me making eye contact "Yes. I want you to get what you deserve." He then unbuttoned my jeans and pulled them down to my knees. I was wearing one of those Victoria's Secret thongs we bought last time we went.

Me: (remembering) Which ones? They yellow one?

Katy: (giggles) Yep

Me: (letting out a sigh/moan)

Katy: O wow, you are really enjoying this aren't you?

Me: Yes, very much.

Katy: Wow. John may not be the only pervert I know. I guess you wanna know more?

Me: Yes, please.

Katy: Ok. Well my ass was full view to them as I stepped out of my jeans and they came over to me as I almost tripped because I hadn't yet taken off my shoes. One of their hands cupped my ass and gave my crack a fingering. The taller 1 helped me w/ my blouse pulling it over my head and from behind the short one unclasped my bra. Standing there in my thong alone in front of John was so humiliating. He started rubbing himself as he looked me over. Then my ass got spanked hard and I almost fell into John.

Me: (I shot a load right then and there, but stayed quiet listening on)

Katy: It hurt Michael and then the taller one says to me "You gonna take that thong off or are we gonna have to rip it off of you? I was frozen Michael. The thong got ripped off of me and the 1st thing John says is "Look at that bush!"

Me: (remembering her well groomed, but full bush that when I saw it the 1st time, I was taken aback by the sight of something you rarely see women keep anymore, but even when I asked her to consider losing it, she refused)

Katy: They laughed at me Michael. I wanted to run away, but I just stood there naked. John then patted his lap. I was confused. Then he tells me "I have always wanted to bend you over my knee Katy."

Me: C'mon Katy! You are going too far.

Katy: No I swear. I laid on his lap as my friend spanked me and while he did that, I watch the 2 of them get naked and God were they ready for me. When I stood up, the shorter 1 says to me "Babe, tell us you want this as much as we do"

Me: (In disbelief)

Katy: I told them to fuck me. From behind, the taller 1 pushed down on my neck as I obeyed and bent forward. My eyes locked on the shorter guy's eyes as I went down towards him as the taller guy had his hands on my hips and complimented John on my red ass. Before I got my lips onto the cock in front of me, the taller 1 slammed into me and God it was immense.

Me: Baby, you got me so hot!

Katy: (chuckles) You are such a perv Mikey. Should I tell you more?

Me: I have already came twice in the last 5 minutes. I can't believe how much this is turning me on.

Katy: Wow. I am glad we are just friends.

Me: What?

Katy: I think your hearing about me being fucked by 2 guys is the climax for you in our relationship.

Me: Katy, I love you. I always will, but you are the one who called me and I have been on the phone with you now for almost an hour and a half. Please don't act like I am the bad guy here."

Katy: (sighs) You are right. I am sorry. It has been a long night. It's almost 5.

Me: You can't leave me hanging. Tell me more.

Katy: (yawns) What do you wanna know?

Me: (stumbling over thoughts and visions of the scene) Should I ask you questions or do you wanna continue telling me about it.

Katy: (2nd yawn) You can ask me questions but I am getting tired.

Me: Were they as rough as you wanted?

Katy: God yes. I got spanked so hard by the smaller guy when he fucked me that I bit the taller guy. I so got punished for that.

Me: Punished?

Katy: they used my ass Mikey!

Me (remembering her ass was off limits as I licked it once and caught all hell as sex was discontinued for a week during our trial run) You let them have your ass?

Katy: I did not have a choice. They sent John to get some Vaseline from the bathroom and he applied it to my asshole as I was sitting on the smaller guy's cock. They both took turns fucking me at same time.

Me: (my 3rd cock explosion listening to her story)

Katy: I never knew how much that would hurt so good and after all those times we had sex with condoms, l never realized how much l missed sex without them.

Me: You did not use protection?

Katy: There wasn't time.

Me: Tell me they pulled out.

Katy: even worse.

Me: Worse?

Katy: John told them to have me suck them after they each fucked my ass. I tasted my own ass Michael. They came hard in my mouth and when l did not swallow all the load, they used their cocks to pick it up and made me clean them. I felt so dirty.

Me: Wow.

Katy: As I laid on the floor John then stood over me and jerked off all over me. At the end, he pissed on me some.

Me: No wonder you hate him so much

Katy: I'm gonna go take a shower and head to bed.

Me: Wait!

Katy: What?

Me: You think you'll ever see them again?

Katy: (about 5 seconds of silence) You do realize I am on my cell phone right?

Me:Yeah.

Katy: l am spending the night here. Good night.

She hung up and the worst heartbreaking convo as I lost Katy forever was completed, but it is one of the best, most erotic stories of my life.