Had a threesome with my FWB and an escort [MFF]

I just looked at my history and it’s been a while since I’ve posted.  Quite honestly, I’ve been having some great sex since my last post, but there haven’t been any encounters that were worthy of being posted on gonewildstories.  That all changed last week.

Skip down to the **** if you want to skip the backstory.

My job requires a lot of travelling.  Most of my travels are to attend conferences and tradeshows around the US and abroad.  As I’m sure many can attest to, when all you do is go to conferences pertaining to one industry, you tend to see some of the same people routinely.  Queue Jessica…

We developed an ongoing FWB relationship a few years ago and try to rekindle it when we cross paths 3 or 4 times a year.  I lead a busy life and so does she (she’s actually much more of a go-getter, so she has even less time than I do).  Beyond that, we don’t really talk.  We sext each other occasionally, usually when one of us is stuck in another City and can’t find a hookup, but it’s sporadic and random, at best.  It’s oddly…casual and businesslike but it’s a great arrangement.  We put in our work and then fuck if we have time.  No strings attached.  I consider myself to be pretty sexually charged Alpha male and and she’s a competitive, type A female and a downright nympho. The sex is amazing and I’d be lying if I said that she isn’t my favorite hookup. 

During some of our sexting sessions, we’ve talked about some of the sexual things we enjoy or have wanted to try.  I mentioned to Jessica that I’ve always wanted to be part of a threesome with two other ladies.  She said she’d done one years ago and it was awkward but has always wanted to try again.  I’ve known that she was also into women, but it was still hot to hear that she had tried a threeway.  I didn’t really take the thought any further as I didn’t think it would be something she and I would be able to pull off together for a variety of reasons.  Queue the internet…

I sometimes use the internet to book escorts (judge me if you’d like, but I’ve never been sure why that’s such a big deal.)  You can see where this is going…long story, short, after some communication and coordination, Jessica agreed to the arrangement.  Queue Olivia…

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A quick description of the parties involved:

**Jessica** – 38, white, shoulder-length straight brown hair, brown eyes, 5’7″, large natural C cups, and probably 160 lbs.  Perfectly proportioned with a spectacular ass that looks great in professional/corporate clothing.

**Olivia** – 31, white, brown hair, brown eyes, 5’5″, enhanced D cups, probably 140 lbs.  – 

**Me** – 35, white, blonde hair, blue eyes, 6’2″, no cups to speak of, 210 lbs.The night of the “event” came.  Due to scheduling, it had to be during the first night of the conference.  Both Jessica and I were slammed all day with meetings and events.  Thankfully, we had exchanged texts during the day to make sure that she still wanted to do this (she admitted to being nervous but said that she did). 

I told Jessica to come to my room about 30 minutes before Olivia came over, which was pretty late at night since we both had client dinners that evening.I showered and dressed casually.  Jessica, clearly having done the same, knocked on my door.  Not going to lie, it was a little bit awkward sitting there waiting for the moment.  We turned on the TV and started going through wine and spirits, which helped a lot.  The expected knock on the door came.  I looked over at Jessica who made a playful nervous face, though I could tell she was still a little nervous.  I traded a quick hug and peck on the cheek with Olivia.  She went over to Jessica, greeted her confidently in similar fashion, and then excused herself to “the restroom.”

I poured/refilled drinks.  I don’t know what other people feel about this, but the first few minutes with an escort can be pretty awkward since both of you (or all three, in this case) know the intentions but feel compelled to make small talk.  The best escorts know how to put people’s minds at ease and make the night flow.  Olivia did just that, bantering casually and lightly flirting with Jessica and I.  Needless to say, Olivia was surprised to find out that we were just FWB’s that were acting out independently dependent fantasies. 

Eventually, more wine disappeared and both ladies were sitting in the same chair with hands on each other’s legs.  Olivia took control and kissed Jessica, which she accepted.  Jessica looked over at me to get involved (we had agreed initially that I would start with the escort until Jessica was ready to join).  Olivia took the hint and made out with me after I moved over towards them.  I didn’t waste much time getting hard and, within minutes, I stripped Olivia out of her clothes and had her down on her knees sucking me off just a few feet away from Jessica.  Within minutes she was deepthroating me and giving me a porn star blowjob.  I looked over momentarily and noticed Jessica had shed her own jeans and was rubbing her clit through a lacy thong she had on.  Her other hand was under her sweater playing with her nipples.  We moved closer to the chair Jessica was sitting on.  Olivia reached up with one hand and touched Jessica through her thong, eventually pushing her fingers inside of Jessica.  Jessica responded with a moan and parted her thighs further.  I reached down and helped her out of her sweater, letting her tits spill out.

With Jessica now seeming comfortable, I suggested we move to the bed.  I laid down on my back and told Jessica to come sit on my face.  I wanted to get her turned on and I wasn’t ready for my pornstar blowjob to end.  I locked my arms around Jessica’s thighs and slithered my tongue up into her wet pussy, feeling her get wetter and writhe against my tongue.  The more time I spent on Jessica’s clit, the more comfortable I found her becoming, to the point that she was bent over and alternating between kissing Olivia and sucking on my cock.  The nympho had finally returned.  I could tell that as more time passed, their breaks for kisses were getting longer and I could tell they were making out hard.  Jessica eventually came twice on my tongue through this process.  

I suggested we switch positions since Jessica’s legs needed a break.  Jessica asked if she could eat Olivia, which Olivia was more than happy to oblige.  I vacated the bed so that I could sit back and enjoy the show for a bit.  It was amazing to see Jessica finger and eat another woman and to hear this other woman moaning and cumming in response (I’d like to think it was real).  I rolled a condom on, got behind Jessica, and slid into her pussy – digging my nails into her ass cheeks and rubbing her asshole with my thumb.  The moans she let out for the next several minutes were muffled by Olivia’s pussy.  I could see Olivia was holding Jessica’s head down to her pussy.  It was extremely difficult to not cum right then and there.  I pushed my thumb into Jessica’s ass, knowing the effect that would have on her and she came again, soaking my cock.  Jessica stepped out of the picture for a few minutes to recover and rehydrate.  

I switched to a new condom and asked Olivia to come to the edge of the bed.  I put her legs over my shoulder and fucked her in a standing missionary position, pounding away and grabbing at her perfectly-shaped tits.  I reached down and choked her lightly (previously discussed) to which I could feel her wetness build immediately.  At this point, Jessica had come back and was sitting on the bed, pinching Olivia’s nipples and rubbing her clit.  I was ready to cum and I told Jessica.  I pulled my cock out of Olivia, ripped off the condom and came all over Jessica’s tits, which was a regular thing for us, but was much hotter this time.

We still had just under 30 minutes left with Olivia and she asked if she should stick around for another round but it was late and neither of us had anything left at that point.  She cleaned up and left.  Jessica showered and stuck around for a little bit before leaving. 

We talked about the events and she agreed that it was awkward at first but that she enjoyed it in the end.  There wasn’t much more said about it. We got to fuck one more time before the conference ended and it was the raunchiest sex we’ve ever had. I haven’t heard back from her since, but am hopeful that our FWB arrangement is still in order. I know these things can get emotional, so I’ll wait and see.

EDIT: formatting

Source: reddit.com/r/gonewildstories/comments/eu1qud/had_a_threesome_with_my_fwb_and_an_escort_mff