First Gang Bang

Ive never forgotten my first gang bang .I’ve been asked if my writings are fact or fiction. They are truly 100% from my experiences and I try very hard not to exaggerate. Some from the more distant past, I take my time recalling best I can , but this one occurred o only 4 days ago. Very fresh in my mind!

Background…

I must be in heat. I’ve been entertaining men I normally wouldn’t of late. Discovered though I like bear types. Who knew! My mind has wandered into areas that I normally would not. You see, I actually try to play safe. Always enforce condoms, steer clear of men with a lot of tattoos (to me it makes someone “dirty”, don’t ask me to explain), no smokers, no one ever permitted to be drunk or high and generally stay clear of pot heads in general. But now, now I’m wanting something new.

Decided it’s time for a gangbang! Not a train with men coming and going. That can be a bit much to manage in a hotel room. I wanted everyone to arrive on time. I wanted to simply say, “isn’t it time you all took your pants off?” I wanted to be surrounded by cocks and my every hole probed at once. Wasn’t picky either where the cum would land. Face, buttocks, mouth or inside me. I was really, really in heat!

Dee’s First Gang Bang, Sissy Photo Stories
What does a good slut do when in heat? I posted an ad. It has become a decent replacement for Craigslist personal ads steadily increasing in size over the past year to a point where all I had to do was say, “what it?” and guys would come and get it.

The Ad…

I’m an organizer though. You might call me anal (pun intended). I posted it two weeks before my next trip and had time after work plus a company paid hotel room. Can’t scoff at that, am I right? I explained clearly the when, the where, the who (me), and the what. What I needed were the other who’s and let them determine the how.

In total 32 men responded, 1 TS and 3 crossdressers. Over those two weeks, some ghosted but I had correspondence with many. More than a few required explanation because they thought I wanted Right Now. I explained it clearly in the ad. Pretty sure clear English was used but nevertheless some meat-heads are just, well, meat-heads. No offense to the meat-heads. I love you all the same but was planning something much bigger!

Just five days prior to my trip, 13 were still engaged though a couple wanted strictly one-on-one. I was actually a little nervous. I’ve had a threesome before but what if 11 showed up? OMG! I don’t know if I could handle it! I tried to talk a CD I knew into coming to help out but she wasn’t in town.

We all know at least half never show and the day before only 7 were still engaged. Okay, 3 or 4, that’s much more manageable.

crossdresser in stockings with dildo inserted
Day of…

Flight delayed, of course, but arrived with plenty of time to prepare. Grab a bite to eat, nothing heavy, hydrate, shave, shower, primp, clean, dress, lipstick, makeup, hair just right, a spray of subtle perfume, heels zipped up and voila! I was ready and if I must say I was looking gewd!!! So I sent the email out to the group of 7 with hotel address, room number and a 30 minute window when I expected everyone to arrive. Made it very, very clear… at the bottom of the hour I will no longer answer the door!

Just to prepare a bit more, I pumped a few squirts of my lube inside me. It’s like Vasoline but way better than any of the liquid water or silicone based crap in my opinion. Gel at room temperature but in me it liquifies enough and stays forever! To work it in further, I used my 8″ travel dildo. I’ve become so loose lately I can pratically sit on it immediately and not break a sweat. That behind me (again, pun intended), I did a little clean up and plugged.

Arrivals…

Time slowly crept by. Checked the room several times, clean, and lighting just right. I must have looked in the mirror 20 times. I hate waiting… then there was a knock! Checking the peephole I saw a middle aged guy looking nervous. Yep, he’s in the right place so I opened the door for him and anyone in the hall to see me. He stood there kinda dumbfounded for a moment, smiled and came inside. Brief hellos and asked him to get comfy. May be expecting others over the next 30 or so minutes. He lounged on the sofa. I offered him some water but before he could answer was another knock!

Again I went to the peephole and saw not one but TWO guys! They were smiling. I let both in. They explained they did not know each other but their timing was just right. So funny! Asked them to have a seat and offered, again, water to all. One asked and I obliged making a show of strutting around in my heels and leaning over a bit too much serving him. He had a nice smile.

sissy crossdresser sucking a nice fat cock
Not knowing what to do next, I took a seat and put up my feet. Legs crossed and nylons glistening for my men. They weren’t bashful and watched me. Time slowly ticked by and enough was enough. Three guys was a good showing! I started stroking my legs and fondling myself. They all almost in unison started touching themselves. I know I was biting my lip and wasn’t too fearful of messing up the lipstick. Thank you Covergirl! Couple minutes passed and one finally stood, kicked off his shoes, unzipped and down went the pants.

He came to me. I knelt before him. Down came his boxers and out came his lovely Johnson! A little over 7″ by my guess. I worked his shaft up and down with my tongue then wandered down to his sack. I drooled over it before the next guy came to me. His I took right in my mouth to firm it up while using my slobber on the first to jack him off. Guy #3 I think was on the sofa, Guy #2 was in my mouth and hand around Guy #1 in my hand when there was another knock on the door! Oh My!

Excusing myself, I went to the door and found Guy #4. He was latino and looked a little skittish but came right in. We had a real party on our (my) hands now! He found a place standing next to #3 on the sofa and I went back to #1 and #2.

The Fun…

Things were starting to pick up. A hand on one, mouth on another, and switching off and lett my saliva run wild. The other two got the hint and approached with their pants and underwear off. I was getting my dream! Surrounded by cocks! None huge but none small and all needing attention. With both hands I’d stroke with a mouth on another then switch off rotating around to give everyone equal and unbiased attention. Okay, the first guy got a little extra, sue me.

Dee’s First Gang Bang, Sissy Photo Stories
I was lifted by both arms almost in unison by two of my evening studs and the plug dropped out. I was surpricsed it stayed in place for as long as it did. They led me to the adjacent bedroom. Earlier I had turned down the sheets and placed ample towels and such. One immediately bent me over and began rimming me. He worked around the plug and eventually pulled it out. His tongue was like silk and fondled my lips, pressing to get inside. I could feel the scruf on his chin between my cheeks knowing it would leave it tender tomorrow but didn’t care. Forcefully, he spread my cheeks and placed himself in my crack with such a behavior I thought He would eat me alive!

Guy #1 was content with my mouth. I gave his shaft such attention and perhaps more than usual given the eager beaver between my cheeks. I had him in my throat several times wanting nothing more than to feel his seed squirt inside my throat! I found #3 and and #4 beside me soon enough. Trying as I could to stroke them but eventually moving #1 #3 and #4 from hand to mouth as often as necessary.

My men repositioned and I don’t who was first but one had found my lube. Feeling the cool, slick gel being smeared between my cheeks and teasting my tight hole. A finger. Two fingers. Pushing in farther. Hooking to find my spot… yep! He found it! Push, push, push on the spot. In & out, in & out. Push, push, push. Mmmmmm. May have been a third finger at some point.

Two were on their backs in front of me. Mouth on one, hand on the other then switching as needed to keep them both slick and hard. Tongue on each giving them a good lashing and licking up the precum as often as I could. One was a little furry and had to pull a hair from my mouth. The other trimmed pretty neat. I thought he was going to cum so I backed off focusing on the furry sack.

sissy crossdresser gets cock in her mouth and arse at the same time
Behind me, I felt the pressure and rubbing between the cheeks. I arched my back for optimal access but the rubbing continued. Slidding back and forth, teasing my hole. Reaching between my legs, I found his sack and gave it a some light touches only. No movement while my hand was there so I think I hit him just right. Fed up after a bit and mouth back on the other guy, I grabbed the cock behind me and positioned him to the place where we both wanted it. He pushed and my greedy slick hole let him right in almost all the way. His motions were great but better was the position he took which was standing over my ass pushing down hands on the back of my hips. Girls, if you’ve never had a guy do you like this, you gotta try it! Hits the spot! I call it the Above Doggy.

Furry was content with my lips locked on his cock. Trimmed was slightly softer now so I gave him more attention with a free hand. First his sack then my mouth applying some warmth and slick to his shaft to strengthen the erection again. Didn’t take long. Then the missing guy made himself known. He was behind me and trying to enter under the man already inside me! DP is really, really, really something I wanted but doubted it was going to work that way. Try as he could, just couldn’t get there on the bed and in that position. So I took matters into my own hands.

Number One…

I went after trimmed cock hard. Sucking and stroking him like trying to restart his heart. He stiffened and I felt the first squirt on my tongue then went down hard. Taking him to the hilt and the remainder unloading in my throat. His body spasmed a few times as I cleaned him. He didn’t seem like a multi-cummer and I was right. I let go of him to focus on furry again. Eventually, he rolled off the bed and left.

Furry was still very content but the one trying to DP me had other ideas. He lay next to furry and asked him to kneel beside my head. Furry got up though I was making it hard as I kept my mouth on him with solid suction till the last moment and let go with a loud pop/smack. They got a kick out of that. DP dick wiggled under me till we were face to face. Doggy dude behind me let up for a moment and pulled out so I sat on DP dick. We lined things up and in he went. Round hole, round peg, perfect fit!

sissy crossdresser spit roasted by two guys
I think he’d done this before as he was giving instructions to both me and the one behind. I lowered myself as much as my hips permitted, arching my back hard. He wrapped his arms around me pulling me close raising his hips going further in. Doggy dude fetched more lube and applied a generous amount to me and himself. I could feel his tip at my hole again partially since the other was already in me. Slowly he worked his was in. A little pain but nothing extreme then… bam! He was in and a bit more pain than I expected! A hand shot back to the one behind me and said to stop for a moment. They were nice, did and asked if I was okay. “Just give me a second” as I caught my breath. OMG! Two in one!

Moving my hips a little was all the indication they needed. Under me he was doing little thrusts. Behind me going for the longer strokes. Furry knelt on the bed I think amazed I was able to do it. I craned my neck to the side and offered my mouth to him. Gladly, he obliged. Angle a bit wrong and I couldn’t take him full in but he was content. My first all-holes-plugged+DP!!!

Number Two…

DP dick, the guy below me, tried telling Doggy Dude to slow down but he wouldn’t. His grunts and groans were an obvious prelude to another seed. He softened minutes later and slipped out. His cum I felt leaking down my sack. So erotic! DP dick wanted out so we took a breather though Doggy had other ideas. He was a non-stop fucking machine! Guiding me to the chair, he sat and told me to hop on reverse cowgirl. I didn’t need a break (but did quickly add more lube), so fuck yeah! Furry was in my mouth again soon enough.

Reverse cowgirl can be exhausting unless you know a trick. One is absolutely bounce but to grind and not just grind but spell. With me hips I spell coconut. First nice a slow ‘c-o-c-o’. Pick up some speed for ‘n-u’ but finally emphasis on ‘t’ increasing speed back and forth. If I was actually writing, imagine working the pencil through the paper for ‘t’. Slow down, bounce more and repeat.

sissy crossdresser sucking cock
As I was bouncing, furry fucked my mouth. Drool ran down my chin and his shaft to his sack. I kept a hand on his sack massaging gently with my drool. He was pushing for full access. Down I went again and again. Each succession allowing his cock to go further till he was fully engorged in my throat. Tongue sticking out and top lip curled in to protect against teeth.

DP dick was back! Apparantly he just needed time to catch his breath. He leaned in from the side and found my clitty. Front of my panties were sopping wet. Licking through the panties then pulled them to the side. He took my little limp sissy thing in his mouth and began sucking. Takes me time to get it up (ED) and often doesn’t last (again, ED). He wasn’t discouraged and countinued which is fine by me! Any sissy that doesn’t appreciate reciprocal oral is a fool in my opinion. I eventually rose to my maximum size, an average thin almost 7″. I leak like mad but quite literally can take hours it seems to actually cum. DP dick kept on though. What a trooper!

Number Three and Surprise Four…

I had just finished spelling coconut for perhaps the third time when Furry slipped out of my mouth and said something to DP dick along the lines of, “watch out, I’m gonna fuck this bitch.” DP dick backed off. Furry lifted my legs from the knees rocking me back onto Doggy dudes lap and stomach. DP dick assisted holding a leg and Doggy dude supported me from behind. Furry lined up and I accepted both much better than earlier. Still a tight fit but accepting all the same. Furry went after me hard slipping out occasionally. Doggy dudes dick slipped out too but Furry kept banging away till he was a very sweaty and finished Furry. He eventually left.

Furry might have been done but DP dick wanted another shot. He allowed Doggy dude to get back in me and hoisted my legs up. He allowed his tip to be teased by the other cock thrusting inside me and made his way back inside me. He didn’t move but we locked eyes while my man underneath thrust himself. I think he was enjoying just that friction. I most certainly was! DP came again just standing there with his dick up my ass. As Doggy started moving again, DP bent over and gave me a kiss, a smile and a thank you. So heart warming knowing I was bringing so many pleasure!

sissy crossdresser in stockings with cream pie cum in her pussy
Number Fiver and Final?

DP went to clean up. When he returned, Doggy had bent me over on the floor ass up. He had to be ready! I thought at the time we were maybe an hour into our festivities but later was surprised we were closer to two hours! He wanted to cum so bad. He had to because he was pounding my ass with long hard thrusts almost to the point of a hate fuck. With each thrust and grunt, I’d rock forward on my knees. His thrusts came more quickly with less out. I grabbed my cheeks to spread myself wide. He came. And came. A squirt some more. A minute of him unloading. Mmmmmm!

I simply collapsed.

DP and Doggy both asked if I was okay. “Mmmm, absolutely.” I said lustfully. DP helped me up and onto my bed. My legs were noodles. He even brought me a glass of water. Such a sweetie. I was dick drunk and asked if he wanted more. What the hell was I saying? Two hours of getting fucked and I wanted more? I can be such a dumb slut at times. He said no thanks but to contact him next time I was in town. Doggy was quieter but also thanked me and said to let him know as well. Then, they simply left me a sweaty, sticky mess on the bed.

I usually do not sleep well in hotels but that night I didn’t bother changing or cleaning up. Heels off, lights off and I just passed out certain to relive tonight in my dreams.

Cast…

Doggy Dude… solid 8″, average thickness for the size, pretty fit and toned, late 30’s

DP Dick… between 7″ and 8″, had The Dad Bod, late 40’s

Furry… good +7″ and exactly that, fur everywhere, guess mid 30’s (need a better nickname)

Trimmed Tommy… maybe 7″, fit in his 40’s

And, of course, yours truly! Dee Sully! Maybe 7″ clitty but who cares, semi athletic, late 40’s
Publicado por cocksucker1966
há 2 anos
Comentários
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prairieFreak13
prairieFreak13 há 2 anos
very well done!
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nylonguyuk
nylonguyuk há 2 anos
sounds hot
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Sara_00
Sara_00 há 2 anos
fab, you are so lucky. its something i have always wanted to do. x
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