To Trust a Stranger Pt. 01

-text conversation-

[ Are you sure you are ready for this? ]

{ More than ready. I've been thinking about this for a long time.

[ Okay... I've got the line-up ready. I got 8 to commit & 2 more "maybes". ]

{ I told you that I didn't have a limit.}

[ You say that now, buuuuuuut.... ]

{ This is a one time deal for me. I'm not holding back.}

[ I'm so fucking hard right now. ]

{ Keep that energy up for Friday. You're 1st at bat.}

[ Then our safe word is *slugger*. ]

The man I'm talking to is setting up a night of pleasure for me and I've never met him in person. When I made up my mind to go through with this fantasy of mine, I found a personals site online and sent a bunch of candidates messages. He's the only one that not only agreed to it but wasn't disrespectful in any of our conversations. We started this relationship of sorts with anonymous emails almost three months ago. We slowly built trust as I eliminated his competition one by one until he was left standing.

I only know him as "Trent" and I suspect that isn't his real name as he only knows me as "Anna" and that sure as hell isn't mine. We quickly progressed to texting and phone calls once he agreed to the rules. He sent me a dick pic, at my request, and I showed him my approval with a picture of my fingers deep in my pussy. It seemed our fate was sealed with that and the planning became our daily obsession. We are two days away now and I can not think of anything else.

[ You double checked that the two rooms are adjoining and have a common door, right? ]

{ Only 100 times. The hotel clerk is getting suspicious.}

[ It's just some of these guys are married & don't want to get caught outside. ]

{ LOL... I am aware. }

[ I know. I just want this to go perfectly... you know, for you. ]

{ And for that, I thank you.}

[ Do you want me to tell them the rules now, or when they get there? ]

{ Do it now. If any of them complain about the rules, they are off the team. }

[ You got it. Hey, you aren't dying or anything, right? ]

{ What?! Why would you ask that? }

[ You just make it sound like this is you ... going out with a bang, or whatever. ]

{ Look, I'm a full on dyke. I love women. But I've never had an actual penis in me. I want to experience it, but it's going to be a one time deal. So, I want to do it big.}

[ Well, this is pretty big. What if you find out you like dick? ]

{ I guess that's a possibility. But I wouldn't hold my breath if I were you. ;) }

[ What are the chances we can at least still keep in touch after this? ]

{ I mean, if the night doesn't end super awkwardly, who knows?}

Trent has taken on a big responsibility. He has agreed to be the conductor to the train of strangers that are going to fuck me. I trusted him to find the participants in this bacchanal event and now I'm trusting him with my pleasure and safety. He's taken the task seriously which gave me time to get mentally and physically prepared.

I've always been fairly athletic, I played volleyball throughout high school and college, but I really hit the gym hard in the months leading up to this to increase my stamina and muscle tone. It felt scandalous to work out at my gym, where other members were training for half marathons or intramural softball games, and I was training to take some dick. Especially when I'd find a hot blonde on the pilates equipment and get her to eat my pussy in the locker room.

I'm 5'6" with dark hair that flows to just below my shoulder blades and bright blue-gray eyes. I've never had too much trouble getting the attention of the women I want to fuck. My tits are just shy of a full "C" cup. My waist is trim. My hips and thighs look amazing in the pencil skirts I wear to the office. I work in a male dominated division of the financial sector. It makes my day when I walk through the office and notice half a dozen hard-ons pointed at me through sensible khakis and gabardine slacks. Sometimes, I close the door to my office, hike up my skirt, and rub my clit to the idea of all those men lusting after something they can't have.

I've always known I was a lesbian. I didn't really date until I was almost done with my degree. I've never had a serious relationship because I'm so focused on my work, but I am starting to want one. That's why I've decided to go through with Friday night. I want to quell my curiosity before I get into a serious situation and miss out on my chance.

[ You at the hotel yet? ]

{ Yeah. I'm soaking in the bathtub, trying to relax.}

[ Sounds sexy. I'm leaving my house now. I should be there in about 30 minutes. The other guys will start showing up 30-40 minutes after that. ]

{ I'm in room 214. Meet me there and we'll go over stuff and I'll give you the key to the other room. }

[ Perfect. ]

{ Hey, in case I haven't said it enough... thank you.}

I had just finished my hair and make-up when I heard the knock at the door. I was suddenly glad the hotel I picked provided robes. Even though I knew putting clothes on was pointless, I had a sudden bout of modesty at the thought of meeting Trent face to face for the first time completely nude.

I took a deep breath and opened the door. Trent was shorter than I had imagined, only about an inch or two taller than me, but he was way better looking than his picture. He had salt and pepper hair that was parted on the side and cropped close. His shoulders were muscular and in his strong looking hands he held a bouquet of roses.

"Trent?"

"Yeah. Anna?"

"Yup. Come on in. You really shouldn't have." I took the flowers from him and his emerald green eyes lit up as he smiled.

"Well, despite what you might think, my mother raised a gentleman."

"I can believe that because we have been in the same room for approximately a minute and a half and you still have not tried to touch me." His eyebrow impishly arched and he took a step towards me and stopped.

"Wait, you are teasing me, right?"

"Yes. We have some housekeeping to do before we get to humping. Literally, keep your shorts on. I feel like I want to hug you though. Would that be okay?"

"I would very much like that." Trent walked towards me with his arms outstretched and I instinctively wrapped my arms around him and nuzzled my face in his neck. He smelled amazing and felt so familiar and comfortable. I was thinking about how much I was enjoying this when I felt the tell-tale bulge in his pants.

"Okay, stud. Maybe we should cool off a bit. Let's go over the evening. Do you remember the rules?

"Yes. No names. I'm going to assign all the other guys a color to be referred to."

"How very Tarantino of you."

"Thanks."

"Continue."

"One at a time. This isn't a gang bang. I get to go first, then I'll go next door to get the next guy. When he's done, I'll select the next guy, and so on and so forth, until everyone has taken a turn. Then if anyone wants seconds..."

"Or more."

"Or more. It's whoever can get it up first goes next. This continues until you tap out or they can't physically perform anymore."

"Right. Now, what are the rules for during the event?"

"Round one is strictly missionary. You will be on your back with your legs spread when they walk in. They can lick your pussy if they want before they penetrate you and they have to finish inside you. The following rounds is the position of their choice, but they still have to cum in you,"

"I want to be a whole mess. That's the bulk of my fantasy. Now what are the absolute nevers?"

"No blow jobs and no anal."

"Correct. Although, you know what? I'm going to break that rule for you and you only. I will suck your dick at the start of the festivities and if you want to try and fuck my ass on your last time, I will let you. But only because you've been so good to me." I noticed the front of his pants started to tent again and that made me smile. "Now, when you aren't in here fucking me, what are you doing?"

"First, I'm repeating these rules to the men next door. Then, I stay stationed at the door to make sure none of them are getting too rough or trying to break the 'never' rules."

"Good boy."

"Guess I should head next door and let the team in."

"I'm going to rub my clit until I'm nice and wet. Make things a little easier. When it's time, just walk in with this ready to go." I walked up to Trent and kissed him as I slid my hand over the massive boner trying to break free of his pants. He groaned into my mouth and I kissed him even deeper. I broke free, spun him towards the door, and slapped him on the ass. "Go get 'em fluffed for me, tiger." He sputtered a bit but did as he was told. Now it was time to get prepared.

I walked to the bathroom and stood in front of the mirror. I let the robe drop off my shoulders and land at my feet. I took both of my tits into my hands and began massaging them until my nipples were taut and rosey pink. I reached into my make-up bag and pulled out a small purple silicone covered device and headed to the bed.

I had already stripped the bed down to the bottom sheet and spread out my own soft fluffy blanket. I lit two candles that filled the room with vanilla and sandalwood. I stretched out on the bed and rubbed my clit sucking vibrator down my pussy to get it slick before I turned it on. I heard the first knock next door and the walls of my cunt fluttered. I turned on my vibrator and almost instantly had an orgasm.

I removed the glistening machine from my clit and licked it clean as I heard two more voices in the other room. I put the vibe on the nightstand and slid my hand down to play with my slick pussy lips. I could hear more and more male voices. I could just make out 11 voices other than Trent. His voice was deep and commanding when he started to go over the rules. I was going to have a dozen cocks in me. I was almost about to cum again when the door knob started to turn.

"What took you so long. And what is that?" Trent walked in, completely naked save for a black bandana covering the lower half of his face. His eight inch cock, that was impressively thick, was jutting out in front of him and gently bouncing with his heart beat.

"I gave all the guys different colored bandanas to help with anonymity. You are to refer to me as Mr. Black for the rest of the night."

"You're so smart." He walked closer to the bed and I leaned forward and wrapped my hand around his cock. He let out a small grunt as I gripped it. I watched as a bead of pre-cum formed at the tip. I gently licked it up. It was salty, but also a little sweeter than I thought it would be. "I hope I'm doing this right.", I asked while giving him my best pout. I opened my mouth and wrapped it around his veiny shaft. I rubbed my tongue along the bottom of his flared mushroom tip and he snaked his fingers through my hair to the back of my head. I was about to protest, but he didn't put any pressure on the back of my head. Instead, he started to massage my scalp. That was a smart move because I instantly wanted to make this equally his night.

I dropped the back of my tongue and opened my throat. My gag reflex made my throat grip his dick for a second and it made him say "fuck", as he sharply inhaled. I pulled my head back so I could breathe and not puke on him. A string of thick saliva connected my lower lip to his throbbing cock head and was running down his ball sack. I started to lean back in to try again and he stopped me. He lifted the corner of his bandana, cradled my face in his hands, and kissed me.

It was passionate and deep. His tongue started to slide into my mouth, so I kissed him harder and more aggressively. He pulled away and whispered in my ear, "My turn."

He pushed me back into the bed and knelt at the end of the bed. I'm normally the one in charge of the bedroom. When he grabbed my hips to forcibly pull me to the edge, I almost came.

Trent placed his flat tongue against my slit and pressed until it was against my dripping wet hole. He dipped the tip in to taste me and then licked all the way up to my clit. He made lazy circles around it and I finally exhaled for the first time all night. He then sucked my clit into his mouth and covered his teeth with his lips as he gently bit down. My hips involuntarily started to buck and he slid a finger into me and curled it up like he was telling my climax to "com'ere". I squirted all over his chin and hand.

"Fuck fuck fuck!" I instinctively tried to run away from his mouth and he tightened his grip around my thighs. "Fuck me. Now! I need your cock!"

Trent grabbed the back of my right thigh in his powerful left hand as he got to his feet. He pressed against the back of my thigh until my knee was almost touching my ear. With his right hand, he was guiding his fat cock to my wet hole. He slid it up and down my pussy to lubricate it and deftly popped the tip in. He looked at me to make sure I was still okay. I nodded and he masterfully slid all the way in until his balls came to a stop on my ass.

My back arched at the slight burning pain that came with being stretched for the first time ever. He stayed still in me as my cunt walls rhythmically squeezed his cock.

His face scrunched up like he was trying not to erupt just yet and through clenched teeth said, "Oh my god, you feel amazing." I looked down to see my abdomen bulge from his giant mushroom tip pressed deep against the top of my cervix. I have never felt so full. He now had both of my legs pressed up and was hunched over me.

I grabbed the sides of his face to get his attention and as I made direct eye contact, told him, "Fuck. Me. Hard."

With a loud squelch, he withdrew his cock until it was almost completely out and then slammed it back in with a sexy grunt. His heavy nut sack slapped my ass and I screamed. He repeated this motion about a dozen times before I came so hard that my vision got dark.

I didn't feel human anymore. I craved that cock like an animal in heat. He started to fuck faster but not as deep. "I'm going to cum." Trent grabbed my hips and slammed deep into me one last time. I felt it pulse a bunch of times. With each contraction he pumped what felt like a gallon of jizz in me. It was warmer than I expected. It felt better than I thought it would too.

His dick started to go soft and it slowly slid out. Without a word, he stood up, fixed his bandana over his face, and walked into the other room. I picked my head up and looked at my reflection in the vanity mirror that was directly across from the end of the bed. My pussy was red and swollen. A river of thick white liquid ran out of my gaping cunt and down my ass.

I barely had time to admire the aftermath in the mirror before I heard the door handle turn. A tall skinny man walked in wearing a red bandana on his face. His dick was thinner than Trent's but a little longer and had a more pronounced upward curve to it.

Mr. Red gave a little chuckle and said, "Well, well, well. Look at this little slut." He gripped his dick tight and started to fuck his fist. The head of his cock turned a deep purple as he walked over to the bed. "Are you ready for the fuck of your life?"

I smirked and replied, "Do your best."

(To be continued)