My Friend's Brother Pt. 05

A continuation.... Please feel free to comment, I love to hear feedback!!!!

*

"I still can't believe that happened," Dawn said to me.

"I know, it was by far the most unbelievable sexual experience of my life," I responded.

Of course, we were talking about the afternoon we ran into my old blowjob buddy Tom at a bar and took him home for a threesome. It was an evening of firsts. Dawn blew and fucked a guy in front of me for the first and only time. She and I blew a guy together for the first time. And then there was the big one, Tom took my anal virginity and it was the best sex of my life. Dawn understood and did not feel slighted in any way. She was just so happy to be there to see it happen.

We were now several months removed from that glorious experience and there was no doubt our sex life was substantially improved. We were honest and open about what each of us wanted to try. But, equally important was the fact that we were also open and honest about what we didn't want to try. It was no secret that I wanted to take Dawn's anal virginity. I really thought I was going to fuck her after she saw how much I enjoyed Tom taking mine. She is more open to it, but not there yet and I respect that. All I know is that when she is ready, I'll be happy to do it!

We kept in touch with Tom over the months and all agreed that our first hookup would not be our last. Unfortunately, between my work travel schedule and Tom's schedule we just couldn't get a time that worked. Dawn and I actually discussed fucking around with him without each other, but knew that was a bad idea and agreed that we would only hook up with him together. We also agreed that we were open to finding someone else to have a threesome or maybe more with. I really wanted to find a woman that Dawn could enjoy in bed. She was definitely up for it too. She'd often tell me how much she would like to lick pussy or have hers licked by another woman while I fucked the other woman. Tom said he had some lesbian friends that would be interested but again, we just couldn't get the time to make it happen.

"I'm in New York today and tomorrow. Then Chicago the next day. I'll be home Wednesday evening," I said to Dawn as I was packing my light travel bag.

"What am I supposed to do when you're gone?" Dawn said in a jokingly pouty voice.

"Let's see," I played along. "Maybe, use your dildo to loosen your ass for me so when I come home Wednesday I can give you the real thing."

"Oh, well that sounds dirty," she continued with the flirting.

"Just how you like it," I said.

"You're the cumslut so I think you like it dirty," she responded.

Dawn had taken to calling me a cumslut after learning about my past with Tom and actually seeing me eat his cum and my own cum. I may have even agreed during our night with Tom that I was a cumslut. It is absolutely true, I am a complete cumslut (at least for Tom's) and not ashamed of it. I actually find it incredibly hot that Dawn knows and supports it. Every time we've had sex since hooking up with Tom she calls me a cumslut and tells me how hot it was to watch me with another guys cum in my mouth.

"Can you promise me you'll figure out a time to have Tom come over? I really want to see him again with you. See if he can bring a woman for me to play with. Or even better, a woman and William for me to play with."

"I know, I was thinking the same thing. It's just hard with our schedules, but I'll work on it when I get back on Wednesday. It would be hot to see you with another woman."

"I know I've always wanted to try it, but never had the guts. After we hooked up with Tom, I figured out that there is no reason not to try it. Especially since you support me. Hell, if you could take Tom's cock in your ass, I can certainly be brave enough to lick a pussy," she laughed.

"Yes, that's mighty brave of you," I kidded back.

My flight was rather uneventful, which I suppose is always a good thing. I went straight to my client's office for a full day of meetings. Things went well, but I had a difficult time focussing all day. My mind kept drifting to my conversation with Dawn about her eating pussy. It would be really hot to see her do it. I was horny all day and was looking forward to a good jerk off session in my hotel room later.

After checking into my hotel room, I took a shower to wash off the travel germs. I always need to shower as soon as possible when I check into my room. Probably just some form of OCD, but it gave me a chance to clean myself up well. Given my state of horniness, this resulted in some cock stroking until I was hard. It also involved a thorough cleaning of my asshole. I soaped both my hands well and stepped out of the stream of the shower so it did not rinse the soap off. One hand continued stroking my cock while the other went right to my asshole. I cleaned the inside of my cheeks before inserting a finger in my tight hole. God, it felt good. Everytime I did this I would think of Tom's cock thrusting in and out of me until I felt his hot cum fill me.

I knew I had to slow down or I was going to cum. I wanted to hold off until I could use my dildo that I secretly packed in my travel bag. Dawn actually bought it for me after Tom fucked me. She saw how big his cock was and figured her dildo was too small for me. She would use mine on her pussy, but was scared to try her ass. We had a few sessions were we would lay on our backs across from each other and watch as we fucked our own asses with our own dildo.

After turning the shower off, I quickly dried myself off ino order to get into bed and start jerking off. I didn't bother putting any clothes on as I knew they weren't going to stay on. I took out my bag and sifted through until I found my dildo. Dawn did a great job in choosing it for me. It was incredibly realistic looking eight inches long, but not too thick. I wasn't ready for something too thick, but I loved the length. I particularly liked the suction cup on the end that allows me to use it hands free. With dildo in hand, I went to retrieve my lube from my bag. "Oh, fuck," I thought to myself. "I forgot the fucking lube! I can't use the dildo without lube!" I knew this because I had tried before and it hurt like hell.

I sat on the bed in disappointment, trying to think of what to do. I'm in NYC, there has to be an adult store close by that sells lube. Yes, I needed lube from an adult store. Dawn and I had tried buying the cheap lube that you find at the chain pharmacy stores only to find it sucks. I could use it in a pinch, but it made my ass itch for a day or two after.

Thankfully I found a store only a few blocks from my hotel. I dressed in a pair of sweatpants and sweatshirt, grabbed my wallet, phone and room key and left on my journey to get some lube. I found the store and surprisingly enough it wasn't a dump. It was actually quite clean and professional. I was impressed by the selection of toys and other adult items.

There were quite a few guys there perusing the aisles looking at various items. Most of the guys looked like they had just come from their investment banking jobs dressed in suits. As I was looking at the lube, a gentleman walked up next to me with a shopping basket filled with items. I couldn't help but take a peek to see what he had. Let's see, cock ring, prostate vibrator, anal beads, and then I saw it. A twelve inch suction mounting dildo. It had to be two inches thick.

"Which do you recommend," he asked me.

"Excuse me?" I responded.

"Which lube do you recommend?" he followed.

"Oh, um, I'm not really sure." I said glancing down again to his basket

"You seem very curious about what is in my basket," he replied. "Anything in particular interesting to you?"

"Um, I'm not sure what you mean."

"It's really pretty simple. You keep looking at what is in my basket so it's obvious you're interested in what I am purchasing. I'm curious if there is anything in particular that is in my basket that has your attention."

"Well, um, not really," I said quite uncomfortably.

"Okay, well anyway, back to the lube question. If you were to put this twelve inch dildo up your ass, which lube would you use?" He asked.

"Oh, um, well, that's an interesting question. What makes you so sure I would stick that twelve inch dildo up my ass?" I asked him

"Nothing in particular. I was just hoping you would and I could watch," he replied.

"Well, you're quite forward, aren't you? I asked.

"Believe it or not, I'm really not. I'm not sure what has gotten into me tonight," he said.

"Well, judging by the contents in your basket, I have a pretty good idea what is going to get into you tonight," I said.

"Hahahaha, that's funny. Maybe it could be more than just what's in my basket," he said looking down at my slowly hardening cock.

"Again, what makes you think I'm into that?" I asked him.

"I'm not sure, but I do know that you are still standing here with a hard dick talking to me about it," he replied.

He was right, I could have walked away. But I was interested in our little dirty conversation. He was of average build and looks with short brown hair. Not heavy, but certainly not in shape like Tom. I decided to play along a bit.

"Well, I can tell you that if you are used to using that monster dildo, you would be incredibly disappointed in what I have to offer in size," I said.

"I'd like to make that decision myself," he replied. "There's no substitute for the real thing regardless of size. Besides, by the looks of it, you seem to be doing fine in the size department," he said, looking down at my now hard cock visibly pushing against the cotton fabric of my sweatpants.

"What are you proposing?" I asked.

"Well, there's some peep show booths in the back of this place. Perhaps you'd be interested in joining me for a show? You can help me decide if I prefer the dildo or the real thing."

What the fuck was happeneng? I came here to grab a bottle of lube and now I have some stranger asking me to go in the back room and fuck him in the ass! This was really messed up, but incredibly hot I had to admit. I was ready to take him up on his offer. Hell, I was already going to jerk off in the hotel room, why not dump my load in him instead? Then, I remembered my agreement with Dawn - neither of us would hook up with someone unless we were together.

"Sorry, as much as I would like to join you, I'm afraid I can't." I don't know why I felt the need to tell him, but I explained my agreement with Dawn.

"Well, you're certainly a better person than I am because I'd be in the back room in a second if I were in your shoes. Well, if you change your mind give me a call, he said handing me his business card.

I took the card and then reached over to grab two bottles of lube. I handed one to him.

"Try this one," I said. "Good luck with that monster,"

I paid for my lube and walked back to my hotel room. I thought about what had just happened during my entire walk. There was a sense of regret that I didn't go in the back room with him. But, then I thought of Dawn and how we've agreed on no more secrets. If I did go with him I would have to tell her. A deal is a deal.

I got back to my room and immediately stripped down naked. I grabbed a towel from the bathrooms and laid it on the bed. I took my dildo out of the bag and laid it next to my newly purchased lube on the towel. My cock was already rock hard as I prepared for my jerk off session. I couldn't help but imagining myself behind my new porn shop friend fucking him in the peep show room. I grabbed my laptop and logged into my favorite porn site and then laid on the bed.

I began slowly stroking my cock while watching a white guy blowing an enormous black cock. This always turns me on because I know Dawn wants to have a black cock to play with. She always tells me how much she would love to share one with me and I have to admit, I would love it too. On the screen, the guy was struggling to take the huge cock in his mouth and I imagined it was me struggling. I put my dildo in my mouth and tried to mimic what was on the screen. Although the cock on the screen was much larger than my toy.

After a minute or so of my pretend blowjob I removed the dildo from my mouth and rose from the bed to go to the bathroom. I brought my dildo with me and found a nice spot on the smooth tile wall to mount it. I returned to the bed to grab my laptop and lube. I placed the laptop on the toilet and couldn't help but notice the white guy on the screen was now bent over the kitchen counter with the black guy getting ready to plunge his cock into him. I immediately hit pause. I wanted my dildo to enter me at the exact same time as that monster cock entered him.

I lubed my asshole with a generous amount and did the same to my dildo. I hit play on my laptop and backed onto my dildo at the same time as the guy on the screen took the huge cock in his ass.

"Oh, fuck," I moaned as the dildo entered my tight asshole. I slowly pushed back so that more could enter me. It felt so good.

"That's it bitch, take my big black cock," said the guy on the screen. "You're my little whore and I'll fuck you when I want."

"Yes, sir. I'm your whore and you own my asshole. Please fuck me whenever you want," the other guy responded.

"C'mon bitch, fuck me. Back your tight little ass on my cock," he said, giving his ass a healthy slap. "Tell me you want my cock."

"Please sir, please fuck my ass with your beautiful black cock. Please cum in me, I'll do whatever you want sir," he responded.

The dom/sub talk was really turning me on. The thought of being totally submissive to another guy was something I thought about, but watching what was playing out on the screen was really getting to me. I slammed back hard on the dildo until my ass hit the wall. I stopped for a moment to feel the fullness of the dildo before picking up the pace and fucking myself in rhythm with the video. I was stroking my cock as the dildo slid easily in and out of my ass. I wasn't far from cumming when a window popped up on my screen. It was Dawn wanting to video chat.

"Fuck, I'm so close," I said out loud.

I don't know why I did it, but I answered her call.

"Hi," I said, seeing myself on the screen naked and bent over. I couldn't see the dildo as it was behind me, but there was little doubt about what I was doing based on what you could see.

"Hi, oh my god Mark, are you masturbating?!?!," Dawn asked in a shocked voice.

"Yup, it's better than what I could be doing though," I said and then explained to her the scenario at the porn store.

"Wow, that seems like an interesting evening. Thank you for not hooking up with him. It means alot to me," she said.

"You're welcome," I responded while pushing back on the dildo.

"I knew you took your toy with you, but didn't expect to get the treat of seeing you using it," She said.

Dawn and I masturbated together frequently. I would say at least one a week so she was no stranger to seeing me in this state. I was a bit surprised she was so easy with the conversation while I was moving back and forth on it.

"Move the laptop to your side so I can see what's going on back there. You know I love to watch you with your toy," she said.

I grabbed my laptop and moved it to the counter. I adjusted the camera so that Dawn could see the dildo enter my ass.

"Oh yes baby, that is hot," she said. "Does it feel good?"

"Of course, you know how much I love it," I answered.

"Do you know how I knew you took your toy?" she asked, but before I could answer she continued. "I wanted to try double penetration with both of our dildos. I've been thinking about you in my ass with Tom in my pussy. Would you like that?"

"Oh fuck yes," I moaned.

The thought of fucking her ass was enough to almost make me cum, but the thought of DP with Tom was amazing.

"What were you watching for porn before I interrupted," she asked.

I proceeded to tell her about the black and white guy and how big the black dude's cock was. I told her about how submissive the white guy was and how it turned me on.

"Sounds like I may have a submissive little cocksucker on my hands. Is that true?"

"Yes, ma'am, you do" I responded

"Ah, I see. Why don't you tell me what you're thinking about as that cock slides in and out of your tight little ass?"

"I'm thinking that it is the huge black cock in the video," I responded.

"Yes, and he's slamming you from behind. Fuck yourself harder and jerk your cock."

"Yes Ma'am," I said as I increased my pace and pushed back hard on the dildo.

"Feel his huge cock in your ass. Oh, he's giving you a good fucking isn't he? Lick the precum off your hand!" she demanded.

I did as I was told and licked the sweet precum from my hand. I then went back and began stroking my cock again.

"Don't touch your cock until I tell you to," Dawn said forcefully. "I want to watch you get fucked by that big cock."

"Yes, ma'am, anything you say" I said, as I pounded back hard. "Oh, god that feels so good."

"That's it baby, you are such a cock whore. We're going to need a bigger dildo for you. Tom's going to be so happy when I tell him you're our cock whore. Maybe he'll bring some friends and they can pass you around filling you with cum."

"Oh my god, I think I'm going to cum," I moaned as I reached for my cock.

"Don't you dare fucking touch your cock," Dawn said. "Put your hands out in front of your cock and fuck yourself harder. I want to hear your ass slapping against the wall. Bury that cock deep into your ass."

I pushed back as hard as I could on the dildo and could feel my ass hit the cold tile wall. My balls were swelling and I knew I was close to cumming. My breathing quickened indicating to Dawn that I was close.

"It looks like my slut is going to cum," she said. "Keep fucking yourself and cum in your hands," she demanded.

I almost fell forward when I started to cum. I focused on keeping my hands cupped in front of my cock to catch my load. This didn't allow me to use them to brace myself.

"Oh, fuck, fuck, fuck, I'm cumming," I grunted as I began to shoot my load.

"Keep fucking yourself," Dawn instructed.

I was burying the cock as deep as I could while still shooting my load into my cupped hands. I had seen videos of guys cumming without touching themselves, but never really thought it was possible.

"What a good boy," Dawn said when my orgasm subsided. "Now let me see what is in your hands,"

I positioned my hands in front of the camera so Dawn could see the full load. It was a good one and I knew what was coming next.

"Drink it," she said matter of factly.

Eating my own cum is something that Dawn finds incredibly hot. Rarely does she not ask me to eat it when I cum. Whether it is off her body or out of her cunt, I always clean up after myself. This time was no different. So, I brought my hands to my mouth and tilted my head back. I could feel the thick cum sliding down my throat. I do love the taste of it. I licked my hands clean and used the back of one to push the drips of cum from my chin into my mouth.

"What a good boy cleaning yourself up like that."

"Yes, ma'am. I wish you were here so I could serve you and make you feel good,"

"That's okay baby, you and I are going to have plenty of time for you to serve me. I think I like having a submissive husband," she said.

"Absolutely, I'm surprised how hot it makes me," I replied.

"Oh baby, you are the best. You know I'm going to have to play with myself tonight. I'll let you know when I do."

The next day I woke to my alarm. It was 4:30am and I needed to get to the airport for a flight to Chicago. I texted goodnight to Dawn last night, but didn't get a response before I fell asleep. I checked my phone to see if she ever responded. She did at 2:30am with a picture of her soaking wet pussy with the caption "Just came. Can't wait to make you my slut." Wow, she really is into dominating me.