My best friend’s name is Kimmie. She and I have known each other for more than 20 years, and I’ve secretly lusted after her since the first day we met. Circumstance never allowed us to be any closer than friends.
We’re both Black, single and in our early 40s. Kimmie runs a Physical Therapy practice and I’m a CPA.
About a year ago, I peeked at a text on her phone. It read: “Hilton on Central Ave, Penthouse. 10:00 PM”. I thought that maybe she had met someone and hadn’t told me.
“Got plans tonight…?” I asked her later.
“Nah…” she answered, in that way she always did when she was holding out on me. “Only plans I have for tonight are home and sleep.”
At 9:45 that evening I was sitting in my car across the street from the Hilton on Central. Kimmie arrived in a taxi — alone — a few minutes later, and went inside. I waited for a few hours before going home, but I returned early the next morning. By chance I saw her leave — alone — at 8:00.
She repeated this activity, almost every week over the next two months. Usually on a Thursday or Friday, and always at the Hilton on Central.
I went deep, deep down the “rabbit hole”, determined to find out who she was meeting. I used all of the investigative resources at my disposal (you need them as a CPA), to discretely find out what she was up to. I caught a break one weekend when she left her phone in my car. She received a notification alert from “Silk Touch”.
After a day of intense digging, I found out that “Silk Touch” was an escort service, one that specialized in client’s with “particular and selective tastes”.
I contacted them and arranged a date.
I spent an evening with a very attractive lady, a blonde named Stacie, mostly talking (but I did get a very pleasant blowjob). We arranged a second date and then a third. On the fourth date I asked about what I’d have to do to work as an escort, and convinced her to introduce me to her “manager”.
After lots of smooth-talk and some subtle manipulation, the obsessive, lustful stalking of my best friend has led us to this moment: it’s 10:00 PM on a Friday at the Hilton on Central Avenue.
I’ve been waiting in the 2nd bedroom of the penthouse for the last half hour. A “Concierge” with the escort service comes in and tells me to go to the master suite, where she has been preparing my client for the evening. She also gives me final instructions before she leaves the penthouse.
In the master suite I find Kimmie. She is naked and kneeling on the bed. Her hands are bound tightly behind her and there’s a leather blindfold covering her eyes.
Tonight, she’s ordered her “usual”: to have someone meet her in this hotel room, dominate and fuck her. She asks for both women and men. She likes blindfolds and light-bondage; she never wants to see her partners’ face — this is her fantasy.
She has no idea that I’m the one that just walked in to help her fulfill that fantasy. At some point I start to realize that this is probably my fantasy too.
“Where to start…?” I smiled to myself. “Mouth or pussy?” My dick is throbbing and my heart is racing.
“He-Hello…?” Kimmie says. “Are you here…?” There’s a slight quiver to her voice. It actually makes me harder than I already am, if that’s possible.
“Yep…” I answer. I’m using my ‘gravely’ voice: my best impression of Christian Bale’s “Batman”.
Kimmie bites her bottom lip. She’s anxious, but I can tell she’s turned on too. There’s a little sheen of sweat on her skin.
I kick off my shoes and strip down to my shorts. I make sure she can hear my zipper open and the rest of my clothes as I toss them on the floor.
I take my time.
“So, what are you gonna do…?” she finally asks straightening up; she’s trying to bolster some confidence now.
“Wouldn’t you like to know…?” I lean in and whisper closely into her left ear.
She flinches when I drag a finger nail across her shoulder. I run the finger down her arm, onto her waist and towards her belly-button. She gasps and wriggles around more, as it slides between her B-Cup breasts.
I finally bring my finger up under her chin, and force her to tilt her head back.
“You’re going to do everything I tell you. Do you understand?”
“Ye-yes…” she replies.
“Good girl…” I whisper.
I reward her by brushing my knuckles against her dark-brown nipples. Kimmie’s breathing quickens as the areola crinkles and the nipples stiffen and grow.
She moans aloud.
My cock is diamond-hard, but I want to tease her as much as possible before I fuck her.
I lean in and kiss her, which seems to surprise her at first, but she kisses me back. Kissing is not a “normal” item on the menu. We’re instructed not to do it unless the client asks for it and both parties’ consent.
But since Kimmie isn’t protesting…
The kissing gets really intense as I continue to tease her nipples. When I start to pull away, she leans in for more.
I smile watching her chase after my mouth.
I take her face in both hands and kiss her again. This time I really go at her, making up for all the times I’ve want to kiss or fuck her all these years. Kimmie’s moans grow louder and her body starts to tremble. When I break away, she’s out of breath and saliva is running down her cheeks.
I grab a handful of her short hair and pull her head back.
“You ready to get started?” I nibble her neck and earlobe.
“Yes…please…” she gasps. “Please…”
I roughly kiss her again and run my hand between her thighs. She’s waxed clean — I know the salon where she had it done — and very wet.
Kimmie cums quickly and loud. Watching and hearing her almost gets me off too. I let her fall back on the bed, quivering and moaning.
“Oh yeah…” I encourage. “That’s was a good one…but I know you got more!”
She rolls around on the bed. I drop my shorts and stroke myself. I can’t wait to fuck her.
I kneel on the bed and rub my dick against her face — pre-cum sticks to her cheeks. She starts kissing the head before taking me into her mouth.
I take ahold of her hair again and start thrusting into her throat. She gags a few times but I don’t let up, her tongue feels amazing. Determined to make the most of this I pull her up onto her knees again. I stand up on the bed and ‘skull fuck’ her with my thick manhood.
I’ve jerked off many times imagining Kimmie sucking me like this.
Saliva and pre-cum are running down her chin and neck. I occasionally give her breaks for air and she anxiously comes back for more, licking away the excess each time.
I can feel an orgasm building so I hold my dick deep in her throat again trying to decide if I should cum in her mouth, on her face or on her tits. If I did her face it might get on the blindfold, which I definitely don’t want because I need her to keep the damn thing on, and I’ve always thought cumming on a woman’s tits was lame, so the mouth it is!
“Aw, Fuck…!” I groan, and my load starts spilling into her mouth and down her chin. Kimmie swallows a lot of it and does her best to lap up the rest.
“Good girl…” I pat her on the cheek and hop down from the bed.
There’s a towel on the nightstand that I use to clean her up. We’re gonna be at this for a while, and I don’t really want to roll around in my own cum.
“When you’re ready…” Kimmie pants, “Could you fuck me, please…? Your dick is really kinda thick…I’ve never had one like that before…I really want your dick inside me…”
Wow! I thought I’d need a few minutes, but I can already feel my ‘Johnson’ coming back to life. I’m extra turned on that my bestie finally ‘knows’ that I have a really thick cock.
I rub my growing dick against her mouth again. She licks and kisses the head.
“So, you want this dick…” I wet my finger and slide it between her thighs and find her clit. “…in this pussy?”
She moans and sucks me into her mouth, spreading her legs to let my fingers go deeper.
“I’ll think about it…” I tease her.
Kimmie’s honey-brown skin is covered in sweat. I can’t believe I’m finally seeing her completely naked. Over the years the closest I’ve ever seen was the rare occasions she’d wear a bathing suit. I’d never known about the crescent-shaped birth mark next to her belly-button or the two small moles under her right breast. My friend is a real hottie, and I’ve always loved watching her.
I’m definitely gonna make this shit last as long as I can! (Besides, the agency has informed me that she’s paid for an “all-nighter”.)
“Roll onto your stomach…” I instruct her.
Kimmie rolls over and slowly inches up onto her knees. I help her into position, so that her feet hang over the edge. I spread her ass and I kneel behind her with my face just inches away.
“So fucking beautiful…” I whisper studying Kimmie’s perfect ass and pussy.
“Omigod…!” she gasps when I bury my face in her ass and assault her with my tongue with the same intensity as when I kissed her before. I intend to make the most of this!
My face is covered in her juices. Kimmie’s lovely feet and toes flex and curl; she squeals uncontrollably. I’m pretty sure I make her cum at least 2 or 3 times in the next twenty minutes.
She’s sobbing when I finally let up on her. I can barely make out what she’s saying.
“P-please…fugme…please…” she begs.
The moment of truth! I stand and wipe some of her cum from my face.
“Is this what you wanted…?” I ask as I take hold of her hips and slowly guide myself into her. I hold my place when my thighs make contact with her ass.
We are both loving this moment.
Kimmie’s is breathing harder, it almost sounds like she’s growling. I’m biting my lower lip, praying that I don’t cum right away — she feels incredible.
I slowly begin to stroke her — in and out. She’s tight and wet, and moving with me, pushing back against each thrust.
“Oh yes…yes….” Kimmie groans. Her head is turned to the left, and pressed down on the mattress. “Give me all o’ that dick…!”
My thighs are slapping loudly against hers as we increase the pace. My cock is soon covered in white-cream each time I pull back.
I suddenly pull out.
“No…!” Kimmie moans, pushing back against air. “Give it back…please…”
I push her aside and lie down on the bed, and then pull her towards me.
“C’mon an’ ride…” I instruct her and pull her leg over my mid-section. I guide my cock back into her.
“Oh fuck…” she moans.
I hold and massage her breasts as she slowly grinds her hips in tight circles.
“So fuckin’ good…so good…” she begins to sobs softly. I can see the tears flowing out of the corners of the blindfold.
I start grinding against her, meeting each thrust. I can already tell I’m going to cum again.
Kimmie’s getting close too.
I give her a few minutes before I start thrusting up into her. Neither of us lasts very long. On my final thrust I empty my load into her, which brings on her last climax of the night.
Her mouth is wide open but no sound comes out. She gasps for air, and falls onto my chest. Her legs go stiff and she jerks and shakes uncontrollably.
I hold her unto it subsides.
“Fuck yeah…” I whisper to myself.
Less than five minutes later Kimmie is snoring against my chest. I’ve always teased her that she sounds like a (small) bear when she sleeps.
I lower her onto the bed and let her sleep. She’s probably done for the night. I could go again, but I definitely need a break.
I wash up, read and respond to a few texts and check on Kimmie again. It’s been almost 30-minutes and she’s still snoring.
She’s done.
I check in with the agency for instructions since this is the first time I’ve pulled an “all-nighter”. They recommend I ask the client and be prepared to fulfill the contract.
I check in on Kimmie again, and unbound her arms to let her rest more comfortably.
I got hard again just watching her laying there like that — legs spread wide, nipples still hard. So, I took a few “souvenir” pictures with my phone.
Its almost 2. I’m certain she won’t wake until morning, so I grab a few winks in the 2nd bedroom. As a precaution, I lock the door, just in case she wakes and comes looking for me.
I wake up at 5:30 — the contract ends at 6:00.
Kimmie is still asleep in the master suite. She nuzzles her pillow, laying on her stomach, her ass spread and raised slightly.
I take a few more snapshots before kissing her on both ass-cheeks to see if she responds.
“Sleep please…” she mumbles. “Too tired…”
I smile and give her a quick peck on the mouth before letting myself out.