My Brother's Best Friend

This one, I have to say, was completely unexpected. I didn''t think I'd ever see Mark* like that. He was just my brother's best friend who was ALWAYS in the house. I didn't really find it annoying because I tend to be oblivious but I did talk shit in my head pretty often, & eventually I started talking shit to him just for fun. Whenever he'd walk in the house I'd have something to say, like, "Oh God, you're here again?!" or "Don't you have your own home" - you know, dumb shit like that. I could never deny his body was on point. He worked out regularly and definitely had one of the best bodies on the block, shit, I'd lick breakfast, lunch and dinner off that - but I don't know why I just never looked at him in a sexual light. Until a few days ago.

My brother was finally staying out over night. It had been a while but once he told me that the lights in my head went on - I was getting laid. Since it was last minute, I fell back on my disappointment , Jay. The night was a late one and Jay was there with me as well as my next door neighbor, Roger & Mark. See Mark is the only person on the block that knows I have something going on with Jay. At around 2 - 3 AM Mark tells my neighbor to go to the store with him, leaving me and Jay to ourselves. I don't understand how many times I can be surprised at how small he is. Whatever, waste of time but at least my kitty got scratched for second.

After about half an hour Mark & Roger come back and Jay leaves once it becomes certain that we're not going to be able to find any weed what-so-ever. Roger leaves around 7 and Mark & I stay up talking. The thing I've always been able to chill around Mark & talk to him, so this was no exception except that this was the longest period of time we'd spent alone.

We lie together on a twin size bed and he holds me. Now this was kinda triply for your girl. I mean, I had just fucked one guy to then be held by another guy I'd never fucked. The world works in such mysterious ways. We didn't sleep. Just laid in each others arms talking shit about anything and everything. That was weird but I liked it. To finally be around someone who's not planning on fucking me - it's like a change of scenery and we all need that sometimes.

So a few days after we talk over text and he wants to sleep with me again - that I should convince my brother to stay out another night. This I know isn't going to happen so I know my only chance is if I fall asleep in his bed and he then goes and sleeps in mine. And that is exactly what happened. Mark, my brother & I were hanging in the room until about 4 when I fell asleep. I woke up sometime around 7-8 to Mark sitting in a chair, wide awake. (This would be completely weird if Mark didn't have insomnia)

I wake up with a start, "Oh shit, it worked!" I laughed.

According to him he was lying down next to me and had just gotten up. That's what must've woke me. So I have him come back and lay down next to me, with my back to him and his right arm wrapped around me. Which means his dick was probably cuddling between my ass cheeks.

As he's running his fingers up and down my thighs and lightly grazing my ass (Im in pj shorts) I can feel his dick getting hard. He rolls over onto his back so his erection can settle. But the line has already been crossed and there was almost no way of crossing back for me.

I grab his arm and drape it back across my body, pulling him closer to me and my ass more into his dick. After a while, I start feeling his dick. Finally, something I can work with. But, I don't want to do this. I don't because he's my brother's best friend. I don't because he's a good guy and I am bad news. & I don't because I don't want be the next Superhead on the block. But of course I do it anyway.

I realize how horny I am and put a finger between my lips just to check, and boy am I WET! I grab Mark's hand and put a finger so he can see & he right there any ounce of self control that was left in his body flew out the window. He kisses me, he wants to do this. With a condom. Hmm, Mark's a smart guy. I think that I have finally been forced into using protection when because of the fear of someone catching us (my entire family is sleeping in the rooms around us) he loses his erection while putting the condom on. The sensitivity associated with blue balls is kicking in. I can help. But not with that condom on. (I'm such a schemer)

I take off the condom and begin giving him head, which I can tell he is unprepared for and very much enjoying. And then he goes in raw. He didn't exactly fuck me though. To say someone fucked me I feel involves some kind of force, it was more like playing a game of pleasure. Not pounding me out but stroking the pussy. I already know if we keep fucking I can teach him the right strokes and it's going to have me going bananas! At one point he even asked me if it was better than Jay's, which it was, by far, thank god. We fucked for quite sometime before the fear of getting caught took over. We lied there for a little while but neither of us could fall asleep. AT 10:30 AM Mark went home, and I finally fell asleep, like a baby.

A Childhood Crush

We were children when Jay told me that I was pretty and that he had a crush on me. Well I was almost a teen and he was a child, almost 5 years younger than me. He was the first kid to ever do that and at 12-13-years-old that was the cutest thing ever. From that day on I always kept him in my sight. He was a cute little boy and every year he just got cuter.

Once he got older his mother decided NY wasn't going to allow him to stay out of trouble h emoted away but visited the block every summer. The day he landed he came to my mothers house. He grew up close to my family so this wasn't unusual. What also wasn't unusual was as soon as he walked in the door I knew this year was the year I was going to have him.

His entire first night we chilled in the crib talking shit and smoking weed. And the entire night I imagined us in every position I could visualize, but never got the chance to say anything. The next morning I sent him a Facebook message letting him know what it was. I'd been wanting to fuck him for a minute now and he was finally old enough.

That weekend I left the block to go stay with my boyfriend so I wouldn't be back until Monday, but over the weekend we talked over text and he made it known that he was going to eat my pussy like it was a gourmet platter and he was a starving.

A couple days later we hung out again, in my brothers room, and as soon as we got the opportunity he ate. And I could barely hold it together being that my brother could walk in at any moment and catch us. And if god forbid that happened I know my brother would not have been happy. At all.

Once I had had enough I laid him on his back, straddled him as I kissed his juicy lips, and began ongoing his pants. I pulled out his dick to go to town when I realized, how fucking disappointing it all was. His dick was definitely not gunna do for me, size wise. Damn. & I had wanted it sooo bad. Either way I went in, and with him lacking it wasn't hard to get most of it in.

After I felt he'd had enough I stood up and bent over so he could give it to me from the back, with no condom as usual (guys are really fucking stupid)... & it's moments like this that make me question so much. Have I been fucked so much that a slightly small penis can barely touch the walls in my castle? Did I have a wide beat up pussy, or was it just his dick? I could barely feel shit.

After a couple minutes I hear a sound and quickly begin dressing again. As soon as we're done, while I'm adjusting my pants, my brother walks in. Almost busted.

Later on that night, we agree to finish in the park around the corner. It's been a long time since I've had sex in public place so I was looking forward to it. There, after I gave him a little more head, just to lube it up, I ride him reversed while he sits on a child's bench under a slide on the playground.

Within minutes, if not seconds, he was done.

What a waste. Maybe Childhood Crushes should stay in my childhood.

****************************************************************

We fucked two more times after (so far). Fine, its not the greatest sex but it's sex and it's on call so why not. And although it's still not great, it's okay, and I realized riding him reversed while he's lying down works pretty well. Especially after a drink or two.

Soon he'll go back to Florida and I'll need to find another on call dick. I wish it was as easy as it sounds.

Cradle Robbing 101

I saw True as soon as my feet touched the cement surrounding the pool. All the way at the other end he sat with only the bottom of his legs in the water, alone. Looking deep in thought and sexy as fuck. It was obvious he worked out some because the curves of his muscles were way to savory to be natural. He had a few tattoos on his body that only magnified how god damn delicious he looked. I knew instantly, as I always do, I had to get this one, and I would.

As I sauntered over to the other end with my daughter in tow, I began thinking of ways to approach this gorgeous stranger. I leapt into the water and as I came back up I turned to my daughter, Ay & said "Wow, this water feels colder than when we were here the other day." After a few seconds I turned to my future fuck and said, "Is it Me, or is this water colder than usual?"

"Yeah, it is. The sun isn't really out today."

Okay, so he talks. From this close I was able to look closer at his body and his tattoos. My favorite is the one across his chest about true love. Not only is it sexy but it's so fucking innocently cute i wanted to die. Most guys will get a tat about Money over Hoes, and Trust No One, and this guy has a tattoo across his chest about love. If only I could cuff.

After a couple of minutes, I start up the conversation around tattoos and we talk about the meaning of ours. My daughter at some point calls out to me (as Mommy) and afterwards he asks for her age (obviously trying to get an idea of my age) so when I tell her she's seven I could tell that was much more than he expected. He thought maybe she was around five. I tell him my age and he tells me his - 17 Really?! I just wanted to throw my self off a cliff. I'm becoming a god damn child molester... Fuck it. He want it. I want it. I'm gunna get it.

Eventually, he asks how long am I going to be in the pool, and I tell him I'll probably return to the second session. He seems pleased and says that we'll meet up then, but if not after the first session we could swap info. Of course I come back for the second session. I stay until 630 at night just playing with him in the pool, dunking and trying to catch each other off guard.

After this we chat each other up over text messages and he even comes to my house to hang out for a few and smoke some weed one day. By this point we had already established that we needed to fuck each other. We had also established the day & if I couldn't get a spot I was going to rent a tellie for the night. It should generally be the other way around but it's been a while since I found dick that was worth it, & I was in need of a good/new fuck. The pictures he had sent me made it clear that he was blessed for a 17-year-old.

Two days before amazing sex is supposed to be had my period comes down, again. My birth control ran out and i haven't had the time to renew my prescription. The day before we're supposed to hook up I tell him what happened.

Before, we go further I also need to note that by this point we've also already established that we won't be using condoms because neither one of us like it. (It never ceases to amaze me how dumb the male species is.)

Now, once I realized my period wasn't going away in time I assumed I had to cancel, but when I call him up and tell him the deal - he's okay with going in while I'm on my period... Raw. Eww. Disgusting ! Yet - a serious turn on at the same time. He's willing to get dirty dirty just to fuck me, Hmm... Okay. I'm just going to start in the shower.

And did We. Oh-Em-Gee.

This boys dick was bigger than I expected. I couldn't even really put more than half of him in my mouth comfortably, and his dick is curved upwards (The best curve possible) which made it a little more difficult to love his dick like it saved my life.

We started in the shower, where i dropped to my knees after having let my tongue explore his mouth for a while. As the water from the shower rushed down my head as I thrusted his gorgeous cock in and out my mouth I thought to myself, 'I'm gunna love this dick'

I got up and threw my leg up as he slightly squatted and pushed his entire package inside me and reminded me how great sex can feel. We fucked there for a few before I got off and stepped out into the shower and bent myself over the bed to get it doggy. Instead of quickly putting it inside me again I am instead caught off guard with his tongue and lips on my asshole. This boy really went to the ass. WOW! And was it on point!

After he puts it in and we go hard, I ride for longer than I think I ever had and even that felt better than usual. As I rode, I grinded imagining I was actually riding a horse like I'd read in a Zane book recently, and Oh did that work. After a while of that, while still inside me, i rotate until my back is facing him and ride him that way and that shit was mind blowing. Because of the curve of his dick I could barely handle it. Then, while I'm on my back I cum so hard that I don't bleed for the rest of the night. Which is good since we went 3 more rounds before finally calling it quits because we were both soar.

Sheesh, it's been a while since I've had a fuck like that, and honestly I'm not so sure if I can keep up with this kid. My body was soar for two days after. Two days that were definitely worth it.

I Can Be To Much To Handle

It was another day in the life. I hadn't hadn't cheated in a few months because I'd kind of fell in physical attraction with one person who I couldn't get enough of but also couldn't see regularly. I was checking my news feed when, "inbox me if your DTF, no strings attached, no fat chicks plz" caught my attention. It was posted by a friend, or rather acquaintance, of TheBoyfriends who I had only recently noticed at a birthday party.Funny thing is when "Nick" said Hi and asked about my kid, I could not remember when the hell I'd ever spoken to him. But he was so fuckable! How could I not remember this guy? I found out later he had cut his hair so that might've been what made him more appealing. Either way from that moment on I could not help the desire that began wreaking havoc on my body. I knew I had to fuck him, but he knows TheBoyfriend so I stood away.

So I stood staring at that message, contemplating. My mind running wild with potential outcomes. Imagining the amazing sex that could take place if I had the chance.

Out of pure curiosity, and me being me, I inbox him with a simple "Hey"

That's all it took. After about an hour of back and forth correspondence and talk of threesomes and what we would do to each other, we agreed that he would come over to my house tonight while TheBoyfriend was at work. I told him I was joking, still unsure of whether or not I could trust him. I didn't want to take any chances of getting caught. One of the number one rules I follow when cheating in order to protect my ass is making sure they don't know TheBoyfriend. I just couldn't resist though, so I invited him over to chill and smoke weed.

Nick show's up that night a little after 11 with his cousin. Originally they wanted to persuade me to have a threesome, listing so many reason why it would be awesome and I would enjoy it. I've been there done that, more than once and I'm just not into two guys banging me out. I feel so used after. Me, a girl and a guy is a whole different story.

Peer pressure, peer pressure, but there was no way I was giving in. They even tried to have me do some truth or dare to break me but I wasn't having it. It wasn't until almost 2am when his cousin left that I got real with him and told him, if I was going to risk it, I couldn't have any witnesses. There was no way I would even kiss him with his cousin there.

Following his cousins exit was the longest make-out session I've had since I lost my virginity. There was something about this boys lips, combined with the fact that my daughter was sleeping in the next room, that had me stuck on his lips and not going further. But after so long of kissing and feeling, me teasing him and gyrating my wet pussy on his rock solid dick, which I could tell would be promising, i pulled my pj's down and slipped him inside me, spooning style on the living room sofa. Boy was he blessed.

I was getting into it, but I noticed it seemed as if he were going real easy. After switching to doggy style I realized what was going on when I would try to throw it back and he was gripping onto my ass for dear life not letting me go hard. The entire time he was about to cum. He finally admits that he has to cum, so I'm like fuck it I wanna go hard. Go ahead cum.

"Where?" he asked sounding confused. Wasn't it obvious? We were already doing it without a condom.

"Inside me. I don't want no evidence around my house. Plus I'm on birth control so I'm good."

Within seconds he lets off his load. The entire ordeal couldn't have been more than 10 minutes. After all the excitement, and such a beautiful cock, it was such a disappointment. His defense was that I'd teased him for so long. Yes, uh-huh. This ass was just too much for him but it okay cause I know next time it's going to be so worth it cause I'm going to make sure there's no kid in the next room and we got enough time for a few rounds. It's going to be Epic.

Surprise Visits Suck

It was the middle of Spring on a Saturday night/Sunday morning. I was on my way home from work at around 4 am. I was bartending about half a mile away from my house. At the time TheBoyfriend and I were on somewhat rocky terms and at that point I was fine with it. I had my own walking dildo, Rich, you lived with me any day TheBoyfriend wasn't around. I never spent a night alone and always got dick when I wanted it. It was pure harmony. But as with any good affair there's always those moments when you almost get caught. This was yet another one.

I about a block away from my house when brother #2 calls me telling me The Boyfriend is upstairs. Shit, where's Rich?

"He's sleeping in your bed," #2 tell me. Fuck. Why Me? Oh yeah I know why, because I'm me.

I walk the next block trying to come up with some kind of alibi as to why this nigga is sleeping in my bed. That was easy. How the fuck was I suppose to know? I just got home from work.

When I got upstairs TheBoyfriend is sitting in the middle of the dining room on a chair with the angriest/anguished look I've ever seen. I walk into the bedroom to find #2 on the airmatress with a bitch and brother #3 on the twin with another, extremely fat, bitch. And they're on a cheap metal IKEA loft bed. How that shit didn't break is beyond me. FInally in my room is Rich, by himself, under the covers. Oh man, does this look suspect, I thought to myself. I try start shaking Rich.
Me: Rich, Rich, get up TheBoyfriend is here, I'm sorry. I didn't know he was coming. Get up and go to the sofa please.
Rich: Fuck outta here. I'm not moving.

and that's all he says and closes his eyes. I was too shocked by the circumstances to react. And I didn't want TheBoyfriend to think anything. A part of me was scared that if I tried to force him out of my bed it would escalate into a serious problem. So what did I do? I left him there and layed across from TheBoyfriend on the sofa.

TB: What the fuck is going on here. Why do [the brothers] have bitches in one room and Rich is sleeping in you bed by himself?

He said this with accusation dripping from the side of his lips.

Me: How the fuck should I know?! I just got here. I just finished working 10 hours to come home and deal with his bullshit and now you wanna come at me? Fuck outta here. I'm too tired for this shit.

And that was that.

Sometimes it's just too easy.

I Hate Locked Doors

It was Fall 2005 and I had just started talking to a guy,"French", who was thirteen years older than me. We hung around the same circle at the time so I assumed he was younger and he assumed I was older. Originally we started getting friendly because at the time I was under age and any guy with an ID was my best friend on a trip to the liquor store. I had already fucked several guys he associated with so my reputation preceded me. After a dropped hint here and there we had decided to hook up one night so I grabbed my bookbag (I was a Senior in High School) and told my daughter's father that I was crashing at my uncles house in the Bronx, went downstairs and jumped in a cab he was waiting for me in.

Although French had a studio in the Bronx he had got his boy to let him use his crib for the night. It was a nice one bedroom somewhere high up in Manhattan - probably around the 200's - and was slightly furnished. Not living room furniture but a great wooden king size bed.

French and I drank and smoked, as we always did on the block, and then hooked up. It was normal amazing sex, he was by far the most experienced guy I'd ever been with so he knew how to fuck me better than any of those young cats were doing at the time. Needless to say I fell in love quick, but that's besides the point- we fucked for hours, and at one point after going doggy style for a while he diced to switch position and when he slams me down on my back we hear a distinct CRACK. But of course that's not going to stop us, would it stop you? So we fuck and fuck and eventually fall asleep, but before falling asleep the first dumb thing happens; for the first time I couldn't find my Nuvaring (the contraceptive ring women can insert into their vaginas so they don't get pregnant.) Eventually I let it go because I searched everywhere and couldn't find it so I assumed he either fucked me so hard it went so deep it's disappeared inside me forever where it will hopefully eventually desolve, or I misplaced it and thought I had one in but never did. Whatever.

The next morning we wake up hungry and French decides to go get breakfast. When he gets downstairs he calls my cell phone and asks me to come down and open the door in the lobby for him. At this point I'm still completely naked, so i just grab the skirt I was wearing the day before and pull it up, no underwear, and just throw on a hoodie I had, no shirt and no bra under. I quickly go downstairs to open the door for him and as we're walking up the stairs, the apartment was on the second floor, he asks me "You didn't close the door behind you, did you?"
Me: "Yeah, why not?"
French: "Oh fuck. It's a slam lock door."
He goes to the door and lo and behold we are completely locked out. Wow. I had never even heard of a slam lock door before. What the fuck is that?? He has no key and the rest of my clothes, my book bag and $900 cash that are in my book bag (I had just cashed my check the day before.)

I sit down and just start laughing. This is great, I'm thinking to myself, I'm locked out, half-naked, no money, somewhere in the city and I have no idea how to get home and I look like a total moron to this guy seeing as it's the first time we hooked up. I should've been born blond.

After we ate breakfast on the stairs in front of the apartment he tell me he'll buy me an outfit so we walk to the nearest strip, which although was only a few blocks away, was far enough when you're only wearing a skirt and a hoodie with no under clothes whatsoever and it's October in NYC and I'm wearing flip-flops. Fucking flip flops! I'm freezing and I look utterly ridiculous. Thank God French was a pretty well off drug dealer and could actually drop $200 on an outfit on such short notice. I walked out with a nice pair of dark blue jeans ad a beige shirt to go with the fresh Timbs. Definitely pays to fuck with a drug dealer at times.

Now although I got the outfit for some reason we couldn't find a store that sold underwear so I was stuck going commando for the rest of the day. When I got home my daughter's father wanted to know what happened to my book bag - I accidentally locked it in my uncles room that morning and he would bring it to me later.

I got everything back that night, not a dollar missing but my pride was a little hurt. I must've looked like such a child to this guy but then again he must like children if he's fucking someone thirteen years younger huh? We continued hooking up and even lived together for a few before he had to go serve some time upstate. We're still friends to this day and always have a good laugh at this but it's only funny now that I know not to close doors behind me if I don't have the key.

Epic Fail

I was at another one of my infamous house parties and everyone was having a great time as usual. That party was just like every other party I had except this was the first – and only – one my ex-girlfriend showed up to. The whole night TheBoyfriend could be seen dancing with her. This did not phase me until people at the party felt the need to point it out to me. Whatever, alcohol makes people loose. I forgive his idiocy.

The party was awesome as always and it was coming to it's end. It was about 4:30 a.m. when TheBoyfriend pulls me over and with more idiocy leaking from his voice he asks: “So, what's good with that threesome with your ex-girl?”

This honestly pisses me off. I hate that bitch. She is an immature slut with no self-respect, an attention whore and is needy beyond repair. Hell fucking No would I have a threesome with her. I don't want her pussy any where near me or TheBoyfriend. So I respond, half-serious half-jokingly, “Fuck outta here. Why it gotta be with my ex and not yours?”

We were fortunate enough to have both of our ex's attend this party and I had already befriended his ex. “Kitty” was pretty and had miles more self respect than my ex. Plus as I figured it, I'd rather have TheBoyfriend stick his dick somewhere it's already been (he'd dated her for two years in high school) then into some new pussy that he might enjoy more than I'd feel comfortable with. Regardless of the shit that I do that's still MY dick.

The reason this conversation even came up was because a few weeks earlier I had brought up the idea of having a threesome because I had never had one that included another female. So when I threw that curve ball at him he couldn't have been happier, “Ok. You should go ask her.”
So I walk through the crowd, grab Kitty's hand and pull her into the bedroom with me. At this point I'm laughing because it seems so absurd and I was pretty sure she would shoot down the idea, but then again, we all know what alcohol is capable of.

Me: “I know this is mad random but [TheBoyfriend] wants to know if you'd have a threesome with us.”
She immediately starts laughing and then says, “You know, I knew you guys were going to ask me that!”

At this point I'm giggling too, we're all fucking drunk, so I ask her if she's willing to do it. She says yes because she's never done it either and she feels comfortable enough at the moment to experience it with us but there's something holding her back. Whatever. I start making out with her and after a few minutes of sucking on her lips, exploring her mouth with my tongue and feeling on her amazing breasts TheBoyfriend shows up and joins the make out session. Before this I had never even considered what a three-person make out session would look like, or if it were even possible but we were all kissing, at the same time.

After a few minutes of this and feeling up on each other TheBoyfriend tells me to kick everyone out because it's 5am anyway. I go back into the living room to find about 6 people still hanging around. What losers. The party is obviously over I don't understand why they need to be told to leave at all. Regardless, I do the dirty work and get everyone either in bed or out of my house completely. This took me almost 30 minutes, so by the time I re-entered my room TheBoyfriend is layed out, completely unconscious, snoring with his mouth open and a little pool of drool forming at the corner. Kitty is laying on the bed, looking like she's bored out of her mind.

Me: “Oh, wow. He really passed out.”
Kitty: “Yeah, he fell asleep while we were waiting for you. He's been like that for a while."

I shake him, trying to wake him, but he is dead to the world. No matter how hard I shake him or how loud I call his name he doesn't even stir.
This is hilarious. I'm laughing pretty hard now because when he wakes up and realizes he fell asleep right before a threesome he's going to be scarred for life.

Me: “Oh man this is fucking hilarious. He's going to be so upset. Are you okay?” I ask her as I kiss her softly.
Kitty: “Yeah. To be honest I have my period so it wouldn't have worked out anyway.”

DAMN IT! Are you serious?! It would've worked out perfect. TheBoyfriend would've had to only fuck me and she would've been there solely for my enjoyment. The perfect threesome. Shot.

Me: "Oh well. At least this is something we'll be able to laugh about. Especially when [TheBoyfriend] wakes up.”

I had a Queen size bed at the time so after I rolled TheBoyfriend over, I lied down in the middle with Kitty on my right and TheBoyfriend on my left. After kissing her for a while longer I fall asleep holding Kitty. In the middle of the night I wake up feeling guilty about not holding TheBoyfriend so I roll over and fall back to sleep holding him. The next morning I wake up and although I didn't get the threesome I've been fantasizing about since God knows when I felt pretty fucking awesome waking up in between them.

Me: “Oh so you're finally awake. Do you remember what happened last night?”
TB: “Oh shit nah. What happened??”
Me: “You fell asleep before I came back! Haaa you knocked out when you had a chance to have a threesome. Hahahahahaha. You're such a dumbass! Ha!

To this day I laugh at him because although I didn't get what I wanted I got something better. A memory that will last a lifetime. I can eventually get that threesome. Shit, I could have multiple threesomes before I settle down but for the rest of my life I can always think back to that epic fail and laugh.