Running a Train on Time

I never gangbanged a lady proper before.  Sure, I’ve had a Devil’s Threeway.  My bros and I have ganged up on a lady at a sex party.  I wrote up rules for a gangbang that never ended up happening one time.  But I was recently able to host my first ever gangbang!  With the blessing of the lucky lady and two other guys, I can finally deliver a solid account of my experience.

Firstly, let me establish my personal qualifiers for a conventional heterosexual gangbang:
1.  No more than one lady
2.  No less than three gentlemen

The lady in question and I had been planning this for months.  Late night pillow chat began our plotting.  It started out as dirty talking, evolved into fanciful imagining, and she finally just sent out invitations.  Time from first mention to moneyshot: 2.5 months.

The first thing we started talking about was who would be attending the event.  Not all of her partners were sent invitations.  When you have multiple partners, they usually occupy different spaces in your life.  Just like you may want a partner or two that you are submissive to instead of dominant, you may want some partners to not be passengers on the man-train.  Similarly, not all of the invited parties accepted.  It’s also totally legit to be uncomfortable riding the aforementioned train.

The final roster was our lady, ethical slut extraordinaire.  There was gent that she and I knew who has always been active in the poly community and we’d shared sex parties with him in the past; he was a large, muscular fellow who was just always had solutions.  It was like inviting Groot to a sex party.  Our third was her partner she had been seeing for some months, who asked that I only refer to him as “The Puerto Rican”.

After the lineup was confirmed, we started talking limits.  For this lady, there were very little.  But it’s always good to have some, just so that people know there is a ceiling on the train.  Some people, in the heat of the moment, will try some silly-ass-shit to a partner who claims to have no limits.  All the guys got to post their limits too!

It was to my pleasant surprise that my co-bangers didn’t identify as completely straight.  But outside of that, the guys didn’t have a lot of pregaming they needed to establish.  After all that was done, it was time for the hardest part about a gangbang: scheduling.

The biggest delay in orchestrating this whole affair was finding an evening where the four of us would be free for a few hours into the night and we wouldn’t be too tired from the day of, nor pressed with work the day after.  I’ve heard good things about using Doodle if you’re planning on hosting a gangbang in the near future.  Time from first invitation to moneyshot: 23 days.

I got the chance to talk with our lady about more than just her limits.  I wanted to talk to her about her requests.  I was already planning a grand scheme, but I always like to cater an intimate encounter.  She was very candid, which I really appreciated:

  1. First Ever DP
    I’d been training her for anal sex these past few months and she wanted to try her hand at getting both holes filled.  I told her I would be glad to oblige her if she thought she was ready.
  2. Bukkake
    She wanted all of us to finish on her face.  She wanted to leave the party looking like a Pollock painting.
  3. Photos
    She wanted something sweet to remember the evening.  Photos would be taken without any faces, though.  Everyone consented.
  4. Guy-on-Guy
    She revealed that part of the reason we were all chosen was because she knows that none of us are completely heterosexual and she knows that we all find each other cute.  She was hoping she would get to watch and live out her yaoi-fangirl-slashfic-fantasies.  She still wanted to be the center of attention, though.  She just wanted a little affection between the fellas.

After all that was secured, we had a launch date. Time from announced date to moneyshot: 14 Days.

We thought about having the four of us meet at a bar beforehand, but decided it was unnecessary.  My work schedule is too erratic and other obligations kept everyone from meeting up any earlier than eight o’clock.  Our lady and the Puerto Rican arrived first, they rushed over here and picked up food on the way.  While they ate at my dining room table, I made small talk and made an extremely visible task of moving my arsenal of sex toys from the bedroom to the living room.  I could see her eyeing up the steel and leather as it found its way out of my bedroom.  She later revealed this was one of the most torturous parts of the evening.

While we were waiting for our third guy to arrive, the Puerto Rican and I opened some champagne and he helped me move my weight bench into the center of the living room.  There we sat, the three of us, drinking and making small talk.  Next to us was table spread of plugs, crops, straps, rope, and equestrian equipment.  She later revealed the spread was one of the more exciting parts of the evening.

Groot, our third guy, showed up a little late.  So once he arrived, we started stripping her down.  Time from complete attendance to moneyshot: 3 Hours 21 Minutes

We stripped her bare and laid her out on the weight bench.  We strapped her down and had some casual caresses and spanks before I made her an offer.  I explained to the other guys that she had requested being able to see the three of us being a little physical with each other.  I explained to her that if I was able to stick a plug in her ass, there would be some totally hot guy-on-guy action.  Naturally, she thought this was a fair trade.

Girl took the plug like a champ.  It was time for us to hold up our end of the bargain.  Before that though, I put a velvet bag over her head so that she couldn’t see what was going on.  All she could do was hear the noises of the pure love that exists between men.  This was my first ever gay-fueled cuckqueaning and she said it was delightful.  Eventually, she started begging us to take the hood off.  I offered her a second deal.  If I took out the plug and replaced it with a dramatically larger plug, I would take off the hood.  There was some hesitation, but she agreed.

Girl took this plug like a champ..if this champ had a Pringles can in their ass.  I stripped the hood off of her and she watched the carousing between the other two guys.  I joined in and we gave her a decent PG-13 show.  I figured her neck would get tired looking up at us, so we stopped hovering over and giggling like a gay Statler and Waldorf.  We all took turns slapping her ass around with every implement in the arsenal.  Finally, I brought out my most dangerous sex toy: my box of dice for playing Dungeons and Dragons.

Rolls for roles, the d6 determined that the Puerto Rican would help himself to eating up her snatch, Groot would fuck her mouth open, and I would use some tools teasing her midsection.  When she had melted all the ice cubes and was an overstimulated mess, we unstrapped her and cast her onto her knees.  She knew just what to do and began voraciously stroking and mouthing the men’s anatomy around her.  In multiple person encounters, I find it can be very playful to engage in some novelty behaviors that simply highlight the peculiarity of the encounter.  In accordance with that, I called for the guys to join me in an activity.

It can be easy to get caught up in a sex party and forget exactly how special it is.  But nothing reminds a lady of how lucky she really is until she has three guys dickslapping her in the face with their turgid penises.  With the three of us drumming her face with our boners, it was like being in the college Marimba group again!

I escaped the drum circle for a spell to put some porno on the big screen.  While porno during sex parties can be distracting, sometimes a distraction can be a good thing.  Most guys are not trained to sustain an erection around other men, but plenty of guys have trained themselves to sustain an erection when there’s porn on.  I have a healthy stock of PMVs (Porn Music Videos), which are a crafted montage of scenes from adult films.  I muted the videos and put them on to be distracting, but not too distracting.  They were white noise for our boners.

Maybe it was inspiration from the videos, or just an irrepressible urge, but we had her on all fours taking turns getting fucked open in minutes.  Time from first penetration to moneyshot: 2 hours 13 minutes.

Tom Robbins refers to penetration in a sex party as “the great showstopper”.  While I agreed with him in my early experience; as I’ve become a more seasoned group sex practitioner, I’ve found that to be less and less true.  I understand the temptation to fall prey to the classical escalator of physical intimacy, in which penetration is the saturday night to climaxing’s Sunday morning.  But penetration as a showstopper is especially untrue at a sex party.

While encounters with two or even three people can progress from start to finish without interruption, an encounter with four or more people is often too exhausting to not take a break.  Pleasing one person should can take a lot out of you.  Pleasing three or more can be like playing soccer.  It’s alright to call a time out a few times to break up the action.

For our lot; we flipped her over, around, and used up all of her holes.  But we did this in spurts.  Our shenanigans would occasionally pause and we would have some water or refresh our cocktails.  We would pause and I would go wash that giant butt plug that I forgot I put there two hours ago.  We would pause and put on silly ass costumes.

That last part wasn’t a joke.

She wanted photos.  The guys wanted anonymity.  I keep a healthy stock of theater supplies, so I got to play dress up with everyone!  Thanks to my brilliant wardrobing abilities, there are now photos of a girl in a Sailor Mercury wig getting spitroasted by Captain America and a Luchedore wrestler while she jerks off the Phantom of the Opera.  This was my favorite part.

After we were done with the novelty sex, we resolved that it was time to get serious.  It was business time; three hole business time.  I figured I would take the back door because I’d been training her to get DP’d with me bringing up the rear.  But the Puerto Rican unexpectedly made a request to fill that hole role.  I was hesitant, I’d never been The Anchor in a DP before!

Let me clarify.  In the Statue-of-Liberty position(NSFW) for DPing, the guy on the bottom is called “The Anchor”.  Because it involves less friction in a significantly less sensitive hole, the guy with the bigger cock is usually the Anchor.  Ergo, I’ve never been the Anchor…

I was a little scared.  But I’d hate to think I spent all that time training her ass to not have someone else fuck it.  Not sharing that ass would be downright un-American!  So with a patriotic tear in my boner, I laid back and got mounted.  She rode me while the Puerto Rican sodomized her.  While getting double-stuffed, Groot came and stuck his cock in her mouth.  Time from Air Tight to moneyshot: 42 minutes.

Being the Anchor was alright.  Anchoring versus sodomizing a gal via DP is a similar parallel to being mounted versus dogging a partner one-on-one.  It was lovely, just not in the ravenous, controlling way I’m used to liking that kind of sex.  I liked feeling his cock rub against mine inside of her.  It was like our dicks were high-fiving for having accomplished her first ever DP.  The muffled moans she vented out of her filled mouth really actualized the whole air-tight experience.  It was something real special.

That being said, it did get a little uncomfortable when the Puerto Rican’s testicles kept percussively slapping against my own.  I was curious if he felt it too or if that’s something you only notice when you’re the anchor.  I wondered if I had been doing this to anchoring guys for years, or if the Puerto Rican just had a distended, pendulous nut sack.

I stopped anchoring before reaching conclusive results.

We took turns with her, exchanging positions.  Penetration may not be a showstopper.  Ass play sure as hell can be, though.  She eventually told us she wanted us to finish on her face.  I explained that I had been holding it in since we started.  I don’t think she believed me, because she said there would be a prize for whoever finished on her face first.  Time from challenge accepted to moneyshot: 38 seconds.

One response to “Running a Train on Time

  1. RachelV

    I may put this on my xmas list.

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