Playing with the Pilot

masquerade

I’m still flying high with the pilot. So far he is awesome and a half!! Last night we attended a masquerade swinger party in the city near where he lives and had a blast!  That and I think we had sex with each other at least 7-8 times.

He wanted me to come up for the party so he offered to pay my gas and get a hotel that would be convenient for me and make it less of a drive.  That makes it sooo much easier for my broke ass, lol, so I was very thankful.  Plus he got us a very nice room at the Hampton with a king size bed that we made very good use of. 😉

The party we were attending had a masquerade theme and you were supposed to wear black.  Black shirts for the men, and either a black dress or lingerie for the women, plus a Venetian mask.  I decided to go with lingerie.  I sent a pic of myself in thisbodystocking to the Pilot earlier in the week and he asked if that was what I was going to wear.  I was like I can, should I?  And he said “Absolutely!!”  So we decided to go all out.  I wore that with little star shaped pasties to cover my nipples and a pair of panties that is basically just a red satiny triangle with black ribbon, making it into a g-string, underneath.  Topped it off with sparkly gold nail polish and black high heel, wedged platforms with a peekaboo toe and a bow at the bottom.  Oh and my mask…. mask

I was very pleased with how things were going prior to the party.  The Pilot says he has never taken a woman with him to a swinger party before but he was the one that brought up a discussion about our boundaries beforehand.  We decided that it would be fine to play with whoever either one of us was attracted to AT the party, and that we didn’t necessarily have to both play but that we would leave together no matter what.  If we played with anyone after the party it would have to be on mutual interest and agreement.

Just having that all decided in advance made me feel a lot more secure and ready for whatever might happen.  I really like that about the Pilot.  He is a planner in other ways too and always lets me know what the deal is with things like the hotel or meeting times enough ahead of time that I have plenty of chance to fit everything into my schedule and not stress.  As a generally really busy, single mom, anything that lets me relax a bit is a bonus.

He was really sweet about letting me know that he is in no rush for anything and if I am late or take a long time to get ready or whatever it is okay.  He has four kids of his own so I think he gets it and says rushing is never fun.  He got the hotel where I would only have to drive a little over 2 hours instead of 3 and would be able to shower and get freshened up and everything too after my trip, which I totally appreciated!

By the time I had dropped my children off with my ex, packed, grabbed a bite to eat and driven up to the hotel, it was after 9 pm.  He planned things out so he arrived right about the same time as me (his drive was like 45 min).  He hugged and kissed me and told me I looked great, even though the air conditioning in my van isn’t working and I was feeling a hot mess.

 HE looked especially hot, in a long sleeved black dress shirt and his head shaved.  He really is a good looking guy, like one you can’t help but steal glances at from time to time and be like “damn”, lol.  He’d asked me to pick up a mask for him when I was at the party store, which was no problem since it was like 99 cents for his, lol.  I’d sent pics of a few and he picked a basic black eye mask.  It looked good on him too. 😉

After checking into the hotel and into our room, we made out just a little bit before I was like I really need to start getting ready, lol.  He was like God, I want to fuck you now but go ahead, don’t worry about rushing and I will go fill the car up with gas and be back in a bit.  So I went ahead and took a shower.  The shower had a see through glass door and I was tempted to leave the door open a crack and tempt HIM to come in there but I didn’t because I knew it would make us really late, haha.  When he came back I could hear him out there cracking up laughing at some TV show, it was kinda cute.

So I got all dolled up and he was liking the outfit.  I put on a black tank top and short jean skirt over it to wear as we walked from the parking lot to the club.  He’d told me it’s in kind of a bad neighborhood, though the club itself is nice, and I didn’t want to be walking on the street like that, lol.

I’d seen the guest list on the swinger site prior so had some idea of what to expect.  This party, unlike the ones I’ve been to here, was a nice racial mix. There were probably an equal amount of black and interracial couples plus a handful of white couples and one or two Latino couples.  There were quite a few singles signed up ahead of time and it was full to the allotment of single males (I think 15).  This club also plays better music, hip hop and rnb, which I find easier to dance to.  Most everyone was in their 30’s-40’s with a couple of older couples.

The Pilot and I had discussed some beforehand about what we are each attracted to and basically decided that he likes women like me and I like guys like him (duh, lmao).  The idea was that we weren’t going to try and push each other into anything or take any for the team and would go for whoever we felt like fucking.  He’d also let me know that he wanted to fuck me in front of people while we were there because he gets off on it.  I was all for that one, since I’m a bit of an exhibitionist myself. 😉  I guess he pretty regularly fucks SOMEONE when he goes to this party too, which is held once a month and he says is his favorite.

As we were in the parking lot some women walked by and the Pilot was like uh-oh, I didn’t know that this one woman was going to be here.  She apparently has it bad for him and he says he doesn’t really feel the same though they have fucked twice, once at least at a party.  He says she just got divorced and has been asking him stuff like how he would feel about being a couple in the Lifestyle.  I asked if me being there was going to cause drama and he said no, but that he’d admitted to her that he was kind of looking to slow down with the swinger stuff but that he wasn’t meaning with HER. 

She was with a woman who had emailed me earlier and who later brought up the Professor!  I’d never met this woman before and she was quite heavy, so not the Prof’s type at all but apparently he had been talking to her about ME?  They didn’t even know each other because she didn’t remember his first name but said that he’d told her we weren’t talking now and that we’d gone to parties together in the past.  I was standing at the bar getting a drink later on when this woman approached me and said that they had been emailing and he was telling her that he thought I must be coming to the party with someone and probably wouldn’t be there alone.  Hmmm….

Wonder why he is digging for information from complete strangers??  He must have seen on my profile that I was attending.  I have noticed him looking at it a couple of times lately but you have to hit a button that redirects you to another page to see what events a person has signed up for.  Not sure why he cares what I am up to if he’s not interested in me himself.   WTF?  There was a guy I used to see a long time ago that would cockblock me at clubs, long after we broke up, and it reminds me a bit of that.  He’d wait till I went to the restroom or something and go tell the guy I had a boyfriend and cause trouble for me that way.  Men are nuts sometimes with their territorialism.

Anyhow, back to the Pilot.  On the way up the steps he is like oh, by the way, I don’t generally mess with other black men’s women unless they make it pretty clear that’s what they want.  Something about how the guys there kind of do that out of respect and that the white guys who go to the party are usually ones looking for BBC for their wives.  I didn’t give it a lot of thought at the time but afterwards I did notice that though there were quite a few black men there, they mostly treated me like they would if I’d shown up with the Pilot as my regular boyfriend and we weren’t at a swinger party, i.e., they were polite and friendly but did not hit on me at all other than one man where he and the Pilot were talking with me and his wife all together, and the host couple that the Pilot knows and has said the guy wants him to play with his wife sometime and he wanted to introduce me. Oh, and one guy when I was sitting alone for a minute. The white guys actually hit on me more, which is kind of backwards from how it usually is, but whatever, haha.

Anyhow, he paid for us to get in and unlimited drinks, which was $40 for him and $25 for me.  The bartender was this totally gorgeous black woman that I liked immediately and asked if she would hold my clothes after I stripped down to lingerie.  She was a sweetheart but according to the Pilot he doesn’t think she is a swinger.  I think he was lamenting that one, ha!

Most everyone had on masks and quite a few women were in lingerie, though mine might have been a little more risqué than most, lol.  I got lots of positive comments on it though. 😉  Like I said, I’m a bit of a show-off that way when I can get away with it.

This party had an interesting set up, that included several rooms, most of which had several black leather couches in them.  A couple rooms also had a disco ball and a stripper pole in the middle on a platform.  One had a massage table and there was a glory hole through one door.  Kind of a largish “glory hole” though.  It was almost the size of my head, haha. In the hallway, near the area that was being used as a bar, there were some trays of appetizers.

After showing me around a bit and sitting on a couch drinking and talking to a few people, the Pilot and I went in one of the rooms with a pole. He pulled me up to start dancing with him, even though no one else was yet.  We were having fun, he is a good dancer, and soon there were a few other couples on the floor too. 

A couple of drinks later I decided to get on the pole and try out some of the new tricks I’ve learned in my class. 😉  It was fun and we got to where he was dancing with me, like grinding on me and stuff. People were clapping for us and shortly after that they announced a pole dance contest but I was done and didn’t join, lol.  The girl who won was a (topless) black girl that knew how to hang upside down and do all kinda stuff on there that I’m not quite up to yet anyway, ha! It was cool though and they gave out a bunch of other prizes, I’m not sure all what for.  The Pilot won some His and Hers KY jelly, but I have no idea why and he was like “we won’t be needing this, haha” (I’m pretty much always wet and willing, lol). 

After all that he asked me if I wanted to suck his dick through the glory hole.  I said sure so he went into one room and I was on the other side.  He peeked through first and bent down to give me a kiss, so I knew for sure it was him, lmao.  I didn’t realize it, but while I was giving him his blow job an audience had accumulated.  He came down for another kiss and asked if I’d noticed all the people behind me?  Haha. 

Then he was like “turn around and back your ass up to the hole so I can fuck you”. So I did and he pulled my panties aside and we were fucking through the hole.  There were a handful of people watching and one woman said “I have never seen a glory hole used like THAT before”.  LMAO.  It was pretty hot.  When we were done people were actually CLAPPING, LMFAO.  He said that on the other side that one girl that likes him had come up behind him and was kind of “helping” him fuck me.  He thought she might have wanted to fuck him too and I said that would have been fine but he said he didn’t want to.

He came over to my side and some of the older, white guys that had been watching wanted him to let their wives give him a blow job.  They were concerned that it might not be okay with me but I said it was fine and the Pilot obligingly unzipped his pants.  One of the husbands called the Pilot the Jolly Green Giant, and it was kind of like, WTF, but the Pilot was good natured about it. They invited me to come sit between the two women, who seemed super concerned that I might be bothered, but I wasn’t.  At some point I joined in with the blow job but just for a little bit.  When one of the husbands started hinting that he wanted the Pilot to fuck his wife, he pulled me up and kind of blew the guy off.  He said he doesn’t like it when guys get pushy like that and it’s clearly the guy wanting him to do stuff more so than the woman being interested.

We ended up going back into one of the pole rooms where a few couples were making out.  He had me suck his cock a little more then climb up on his lap, facing him on the couch, and ride him.  He later said he had a good view of the couple behind us fucking while we were doing our thing.  I just noticed a woman watching from the doorway and occasional people stopping by, lol.  We danced a little more and he pulled my panties aside and started licking me while I was backed up against the pole in the middle of the room. 

He never came at the party, but did at least 5 times after we got back to the hotel, maybe 6, when it was just the two of us.  😉  On our way out we stopped to talk to people and the woman that likes him and the bigger woman were there and she was obviously wanting to talk to him. When we got back to the car, where we had left our phones, he showed me that she had texted him “I want to suck your dick” while we were in there.  Oops.  She again texted him around 3 am, while he and I were busy fucking and he didn’t see it until late the next morning.  I kinda felt bad for the girl. 

There seem to be a couple of women like that who are into him and he’s not seeming that interested.  Some others had wanted him to go to some mud tournament deal they had going on today too but he was at the hotel with me.  I probably need to watch out that I never become “that girl”. :p  For now though, he seems pretty into me and even wants to drive all the way here again soon.  Still trying to keep things at FWB level for now and so far so good on my end.  I can see why women like him though!

The only little red flag that has popped up is that he has told me he was divorced 4 years ago and at first was saying he’d been in the Lifestyle about 4 years.  Then he brought up something that made it sound like it had been a lot longer so I asked again how long ago he got into swinging and he says he first did it about 10 years ago but stopped when he was deployed.  Well, he also mentioned before that his ex- wife wasn’t into swinging at all or anything like that, so presumably it was done behind her back.  Hmmm… Not that I’m an example of a shining beacon of faithfulness or anything, I did have an affair myself.

Back at the hotel we fucked and fucked, lol.  It was very good and we’d finish and I’d think he wanted to sleep but then he’d want to fuck again.  We finally fell asleep sometime after 4. He woke me up the same way he did last time, sticking his dick in me from behind, at around 7 am.  After a couple rounds I got a shower and we went down to enjoy the hotel breakfast.

Then back to the room for more sex.  And more.  I was amazed at how much he came after that much fucking, lmao.  I was a little worried once that he may have cum inside me because we weren’t using a condom and he acted similarly to how he does when he’s about to cum then stopped for a little bit and started kissing me while he was still inside. IDK, but I think I’m past the fertile time of the month anyway so not too concerned.  Years of natural family planning has me still paying attention to that.

Toward the end a maid actually came and knocked on the door while we were in the middle of it all and he was like “um, could you come back later?”  We were surprised she couldn’t hear what we were up to as I was not being especially quiet.  He’d been teasing me before that if I kept saying “oh my God” people were gonna think we were in there having church! 😉

So anyhow we got back at it and he pulls me over the side of the bed and was doing me from behind with my hands pinned down under his and I came really hard, then he just kept going because HE was about to cum, so I got kind of extra loud that time.  We stop, he came all over my back, then goes to get a towel to wipe it up and after a pause we hear the vacuum start in the room next door.  LMAO.  It was pretty clear the maids had been listening that time, because they waited until AFTER we are done with all that noise to turn on the vacuum cleaner.  We were cracking up.

He was even like “now you have material for your blog”.  He knows I write one and I’ve mentioned it has some erotic content but not elaborated.  I think he’s thinking I write erotic stories.  Haha… He’s brought it up before and I think enjoys the idea of being blog fodder.  If only he knew…;)

4 thoughts on “Playing with the Pilot

  1. I’m so happy for you! It seems like you’ve found a good guy this time, and that you’ve got a good understanding between the two of you. AND he’s a legit stud! Enjoy!
    On a different note, I’ve got a friend who lives in the south (no idea where you live) and is interested in possibly getting into the swinging scene with her husband. She hasn’t had much luck finding out about events and such…is the message board you use a local thing, or is it a national type thing?

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s