With my third visit in the books and thinking about how things went down the night before, while I am at work Tuesday afternoon, I get a Kik message from Andy.  I didn’t recognize the username but the message included an introduction with him addressing himself as well as calling me my name so I figured it was legit.  Seemed a little odd given that all of my communication to date was with Jess but I didn’t care.

I ask him what’s up and he replies asking me if I was serious about staying at a hotel close to PDX Thursday night.  I told him that I was serious and that I already had the hotel.  He then asks if I could do him a favor.  Given that I had three sexual encounters thanks to him and Jess, I ask what the favor is.  His “favor” was asking if I would be interested in taking Jess out to dinner and messing around in the hotel afterwards.  I immediately say yes but also ask what’s up.  Turns out that Thursday was their 5th wedding anniversary and he was called out of town for work that morning and wouldn’t return to Oregon until Friday and would therefore miss their anniversary dinner.  He really liked me as a person and thought that maybe I’d lend a hand and help them out so Jess isn’t alone on their anniversary.  He then shares that Jess has no idea that he reached out to me and it would be a surprise for her.

I ask how he plans on surprising her with a visit with me.and he elaborates that she has always had a fantasy of going to a hotel, knocking on a door and having a strange male open the door and she fucks him.  I am thinking, “that’s kind of hot” and ask if he thinks she’d really do it.  He says that she would because he got off on the idea too and she wouldn’t want to disappoint him.  He also adds that he wasn’t 100% comfortable with sending her to a perfect strangers hotel which is where I came in.  He wasn’t going to tell her that it was going to be me to open the door so the mystique of going to a strangers room was still going to be there for her.  I reply that I am all in for Thursday night and he signs off asking that once I know the hotel and room number to let him know and she’d be there at 6PM on Thursday.  

Time crawls from the point we signed off Tuesday afternoon to Thursday just from pure anticipation!  I get to the hotel at 5-ish, have a couple of drinks in the hotel bar (they were free - manager’s cocktail reception) and I shoot Andy my room number.  He replies “have fun” and that’s it.  I finish my drink and head back to the room to shower and shave and wait for 6PM to come.  6PM comes and there is a knock on the door.  Rather than open it right away, I wait for her to knock a second time just to add to the mood.  Shortly, after the second knock I open the door and there stands Jess in a skin tight, little black dress with cleavage galore and it’s so short it barely covers her ass.  I immediately get a semi-hard on just at the sight of her standing there.  She sees that it’s me and goes from a smiling happy face to an even bigger smiling face and says “I am so happy to see you”.  I invite her in and close the door and we immediately start making out.  

Within 30-seconds we’re both naked and on the bed.  She gave me one of her super blowjobs and I didn’t last very long because she was so damn good.    It was awesome and swallowed every drop.  I then ask if I can return the favor by going down on her and she says yes.  She is already super wet and in addition to the licking, I get three fingers in as she moans with pleasure.  This goes on for a bit and she cums a couple of times.  Things come to a stop and we lay there for a bit and chat.  She thanked me for being there and agreeing to see her on their anniversary and hosting them the few times I ‘ve been to Oregon.  I reply by saying the pleasure is all mine!  We then decided to get dressed and head to a steakhouse near the hotel for a bite to eat.  She puts on her little black dress with no panties and off we go.

We got to the steakhouse and as we walked in, I would have to say almost every dude that saw us walk in was staring at us.  I didn’t care as I was 1,500 miles from home and she didn’t care one bit.  Even the hostess was checking her out.  We get shown to our booth which just happens to be in the corner of the restaurant and she gets in on one side of the table and as I go to get in on the other side so we can face each other while we’re eating, she tells me to sit next to her.  “Of course”, I say so I slide in next to her.

The waiter comes and takes our drink order and I order a local IPA and she orders a whiskey neat.  The drinks come and we start sipping on them when she whips out her phone and asks if it's okay if we Facetime Andy.  I tell her that it’s not a problem and also tell her she doesn’t need to ask me anything.  If she wants to do something, just do it.  With that she rings up Andy and she sets the phone against the napkin dispenser in the middle of the table and includes me in the frame.  Andy picks up and he immediately smiles when he sees her..  They wish each other a happy anniversary and he apologizes for not being there and she then thanks him for setting her up with me as she grabs my arm and kisses my cheek.  They make small talk for a bit when he asks if we’re alone and she tells him as alone as one could get in a restaurant.  Luckily the next booth was empty as was the table closest to our booth.  He then leans in and tells me to reach under the table and start fingering Jess.  I do so and she’s already wet.  Even wetter than before when we messed around in the hotel.  She’s trying to keep a straight face and not moan when the waiter comes to the table and asks if we were ready to order.  He immediately sees what’s happening, turns around and walks away.  

Andy didn’t see the waiter but could tell something was up and asked what happened.  I pull out my fingers and we tell Andy.  He laughs and says “good”.  He follows that up by saying he is going to sign off but asks if we could Facetime him later.  She says she would, tells him that she loves him, says goodbye and hangs up.  The rest of dinner was pretty benign.  We ordered our food, had a few more drinks and talked some more.  I asked her about their relationship and in a nutshell each of their first marriages were sexless and her ex was verbally and emotionally abusive.  They met at a mutual friends party one summer and within a few months both were divorced and married to each other.  She called him her soul mate.  She really loved sex and while Andy did too, he really got off on sharing her. 

We finish dinner and head back to the hotel and Jess uses the bathroom while I sit on the couch.  She emerges from the bathroom wearing a one piece, black fishnet bodysuit and high heels.  Sexy as F.  We start making out again and groping each other when she stops and tells me that we need to call Andy.  She gets up, grabs her phone and Facetimes him again.  He picks up, she’s what she’s wearing and knows we’re back in the hotel.   More small talk about how dinner went, etc. when Andy then says that he’d like for me to fist Jess.  I am like whoa, really and but say yes.  With that, Jess gets up and grabs her bag of goodies and comes back with lube.  She lays back on the bed as she hands me the lube.  I start by getting two fingers in her snatch and the lube isn’t needed because she’s so wet.  She’s holding the phone trying to include me playing with her pussy in the shot when he says he can’t see and asks Jess to give me the phone!

So there I am, fingering Jess with one hand and holding her phone with another.  I am now up to four fingers in her pussy when Andy tells me to bring my thumb into my fingers and slide everything in.  He also tells me to lube up my hand.  At this time, when I go to start sliding everything in, I am finding that I am getting some resistance.  A fair amount actually and the more I push, the louder Jess screams.  To the point where I am thinking I might be hurting her.  Andy tells me that I am doing fine, to keep applying pressure and despite the sounds Jess is making, she’s really enjoying this.  In a very loud voice between the moaning, Jess blurts out “Yes, keep going”.  

I continue to push and the moans get louder and louder.  I am really turned on and kind of freaked out at the same time.  Finally, when I get to the knuckle at the base of my thumb, my entire hand more or less gets sucked into her pussy and she screams “YES!”.  Andy then tells me to start moving my hand in and out and Jess is shaking, screaming and cumming all at the same time.  I am blown away.  This goes on for a bit when she reaches down, puts her hand on my wrist and pulls my hand out as she starts gushing all over my arm, hand and bed.

Andy asks for me to hand the phone back to Jess and he asks if she’s happy to which she says yes. He says he’s happy to, wishes her good night and signs off.  Jess sets the phone down and catches her breath and I am still sitting there more or less speechless.  I am still at full attention so she crawls towards me, pushes me down onto the bed and starts riding me with her glorious tits in my face.  Not sure what happened but with me just fisting her, it turned some kind of switch on in her and she fucks the shit out of me.  Rode me like I had never been ridden before.  I nut inside her and she kept riding me.  I am still hard and she kept riding.  Not sure how long it was but she kept going and came three or four times as I could feel her warm juices on my upper thighs.  It was intense.  She cums one more time and rolls off me and we just lay there covered in sweat.  Maybe 30-minutes go by and we just lay there and don't really say much.  I am just reveling in the moment.   

After a bit she leans over, kisses me on the cheek and says “let’s go take a shower” and off she goes.  Who I am to say no so I follow her in the bathroom.  We hop in the shower and take turns scrubbing each other’s bodies.  A kink of mine is showering and soaping up a woman’s body so it didn’t much for little me to show he was ready for more.  She sees what’s going on and immediately drops to my knees and sucks me off right there in the shower.  Given that I had already nutted twice that night, the third shot took some time but Jess never wavered and got the job done.  

We finish up and head to my suitcase and throw on some boxers while she finishes up in the bathroom. She came out dressed in some cut off jeans shorts, a tank top with no bra (side boob going on for days), a Seattle Mariners hat and flip flops and looked spectacular.   We embrace, kiss and she makes me promise to let them know when I come back. I promise her I will and tell her it’ll be 3 to 4 weeks.  She smiles, says “see you then” and off she goes.