Days had passed since Hannah and I had arranged to have sex for her viewers. She had posted on her site of our upcoming scheduled sex session, to be viewed live for the first time. Her viewers craved the sex and we’re bored of her solo play. We were both hoping for a good turnout. I was depending on it. Hannah told me of all the obscure and fetish requests she received from random men. “Think of the most sedistic sexual shit and double it” she would say to me. The requests were as vanilla as french kissing during sex to BDSM with a paddle and my testicles stepped on in heels. I happen to like my testicles not being crushed.
I was becoming nervous, not that I had to worry of extreme things like that, but of the expectations. It would be my first time with Hannah, a good friend my roommate. My first time being watched, even if they are strangers I don’t know. Let’s also remember the monotary gain that I needed. I was literally fucking to save my life. The night before our live session Hannah and I sat down to settle some final details.
” How exactly is this going to work?” I asked her.
“I’m charging $50 to watch it live and $40 to buy the session after. The people watching can donate more if they want and can make certain request for money.” She spoke so confidently, as if she had done this exact thing before.
“How many people do you think will watch?”
Hannah paused a moment. “I’ve had 60-70 watching one of my live strip sessions, but those are much cheaper. I’m not to sure.”
I go quiet a moment, thinking about every scenario in my head. Friends seeing this video, not making enough money for rent. Most importantly, what if I’m not good with Hannah and this ruins our friendship. “What are your hard no’s?” I say out of curiosity.
“No bathroom stuff or degrading me. David, you won’t break me. Just enjoy this and have fun.” She says with a smile.
I nodd as I sip my beer. “Sounds good to me”. The truth is I’d take Hannah right now, right here if I could. I can’t get that night out of my mind, the night I saw her spread out on the floor in her black lingerie. She never wears revealing or provocative clothing, so I’d never wondered what was under the clothing. But I saw Hannah, for what she is as a woman. Her beauty, her grace as she pleasured herself. I must say, my excitement for tomorrow is all I lust for.
The next day is business as usual. I attempt to reach the unemployment office a unsuccessful 135 times via telephone. I read a bit, but the day drags. Hannah and I don’t play until 8:00 that evening, and it’s barely past 2. Out of pure boredom I decide to take a shower. I often do this as it relaxes me, and lets me clear my mind. My music is playing loudly, I don’t hear the door open. My eyes are closed as I wash my hair, when I feel a cool draft. My eyes open to reveal Hannah standing with the curtain open, looking at me.
“Figured I should see you naked before tonight. Normally I at least get food before I fuck someone” Laughing as she says it.
“Well your getting this tonight. I might have some butt end of bread left, go make a sandwich” she’s looking at my soapy, unerect penis which looks even smaller because the hot water is running out.
“Now we’re even I guess.” shutting the curtain again, she disappears out of the bathroom.
That felt….normal. It wasn’t weird at all, and of course she walks in the one time I don’t happen to be masturbating I think to myself.
The remaining hours trickle by. My nervousness has turned to anticipation. My anticipation turns to excitement. At 7:00 I hear the shower run in the bathroom. Hannah is beginning to prepare. The final hour disappeared and I’m waiting in the living room. Hannah finds me waiting, she’s holding her laptop. She sets it on the table, so the camera faces the couch.
“Here good with you?” She asks.
“Works for me, couch is better than the chair.” I tell her.
Hannah opens the laptop, logs into her site . “Holy shit! There is already 100 people waiting!” Hannah yells enthusiasticly. “Are you ready David?”
“Whenever you are Hannah.”
She turns to look at me from her laptop on the table. “Ok! We’re live in 20 seconds.”
Hannah rises up, wearing her gray robe. She walks to the couch, towards me. Smiling at me we hear a loud ting. We’re live, she doesnt speak but I can read lips.
She unties the front of her robe, and drops it to the floor. Kicking it off to the side she continues to walk to me. Hannah is stunning to put it politely. She does a 360 degree turn, letting me take her in, and our viewers. Hannah is in a matching panty set. Her bottoms are a tight fitting, booty style underwear blood red. The fabric hugs her hips and ass well, and perks her ass up almost a heart shape. Her blood red bra fits her perfectly. Pushing her breasts high up on her chest, the see through lace allows me to just make out her nipples. Hannah walks to me, I spread my legs. Standing so close to me I grab hold of her, one hand on her high hip, the other directly on her soft but firm ass. I pull her near me, she sits directly on my lap. Hannah leans close, and kisses me.
Once roommates, now lovers, Hannah’s tongue and mine meet, and exchange Hello’s. My penis swells fast against my sweat pants. She begins to grind her pelvic area on me, while never breaking our kiss. She only breaks our kissing to get me to remove my shirt, which I happily do. My penis is erect and I reach down to reposition it, to allow her to grind on it while we kiss.Hannah releases our lips, and lets out a moan as she grinds on me, her hips moving at a brisk pace. I sit motionless as she grinds. Through my sweat pants I can feel her intese warmth, like a furnace. I move her hair off her neck and kiss it gently. My hands move to her ass as I help her increase momentum as she grinds. Her moans increase as she grinds,faster and faster. She moves in and embraces me in a hug, lifting her ass in the air and off me I can feel her quiver. “Fuck I came!” A out of breath Hannah moans. With her ass off me and partially in the air I take my hand, reach under her and feel her wet underwear. I can feel the indentation of her vagina, with only fabric holding me back.
I move her underwear to the side, and with one finger I feel her labia. Wet and inviting I slide a finger in her. Slowly I slide in and out of her. Hannah wastes no time. She jumps off me, moves to her knees. She helps me take my sweat pants off. My penis is different than she saw in the shower. The shower had me soft, looking un desireable. However now I am fully erect, my 7.5 inch circumsized penis is rock hard and thick. The girth is what woman have said is my best feature.
Hannah repositions me better for the camera, then eagerly grabs my penis’s base and pushes her mouth down on it. Just moments her tongue against mine, now she uses that same tongue to lick up and down my shaft. Her hand continues to jerk me as she licks and sucks. Her mouth is warm, smooth and heaven. She is skilled at this, that is evident. I rub her back as she bobbs her head, unclamping her bra, exposing her breasts. Her hand motion intensifies, her mouth tightens. My penis in ectasy is unable to control the urge to cum. “I’m so close” I warm her. Hannah never stops, she continues to suck. When I begin to cum, Hannah places just my head in her mouth using her hand to milk my penis of every drop. Once she is satisfied I’m done she moves on her knees near the laptop, opening her mouth to the strangers on the screen. Showing off her cum reward, she smiles and tilts her head back. Every drop of cum swollowed.
Even after my release, I want more. I move to the floor and motion her over to sit on the couch. I help her remove her underwear and sit her down on the couch. I move her legs apart, revealing her most intimate area. Smooth and hairless, I’ve never seen such perfection. Her cliterous enlarged from stimulation, her labia wet around the edges. I dive head first between her legs and taste her. I use my tongue to pleasure her. Her hand grabs hold of my hair and she pushes my head down hard, using me where she wants. My tongue is hers to use. I remain erect this entire time, ready to go again at a moment’s notice
Without notice she moves my head and stands up. She walks off screen to her room. She comes back with the large dildo from the other night and lube. She leans down to my ear and whispers ” You’re gonna need to fuck my ass”. Hannah gets in front of the camera, begins using the oversized dildo on herself. I hobble on my knees over, open the lube and drizzle some on her ass. I’m gentle with her as I massage her ass with my thumb, watching from above as her lips grip the massive fake dick. With my finger in her ass I can feel the oversized dildo move in and out of her vagina. “Fuck my ass” Hannah says loudly. I stand up and stand just over her, still erect I push inside her ass, with little resistance. I’ve never had a woman want anal before, it’s different but in a good way. It’s a intense pleasure. Hannah moves her toy in and out of her faster now that I’m in her ass. “Oh fuck, oh fuck I’m about to cum” she moans aloud. I fuck harder, close to cumming myself. I normally last longer than this but Hannah is magical. I begin to cum in her when she pulls the dildo out of her, quivering and pulsating she gets to slip away. I grab hold of her hips and hold here in place. Her orgasm seems intense, as she squirts ever so slightly on the floor. I release everything I have into her, a second time.
Exhausted I pull out of her, my cum is much clearer now and begins to exit her with gravity’s help. I lay on the floor, and Hannah near me. Both of us breathing heavily. “That was fun” she says. Hannah crawls to the computer. “Hope you guys enjoyed that! Thanks for all the support, see you guys later.” She tells these strangers as she closes the account. “David get over here, look.”. I also crawl over and see the number. 137 people paid to watch us fuck. At $50 a head that’s almost $7,000! “Are you serious Hannah! That’s amazing!” I eagerly say. “Just from one session.”
I watch Hannah stand up and walk to the bathroom. Nude, beautiful and freshly fucked she looks flawless. That is what a woman is supposed to be. She was incredible tonight. I want to go shower and clean her, but I’m not sure how that would go. I roll on the floor to my back and see my penis is limp, but wet from lube and cum. I think I’ll just lay here a few moments more, I’m exhausted from sex but that was the easiest day of work I’ve ever had.
Source: reddit.com/r/gonewildstories/comments/gv7ko5/hannah_my_roommate_and_boss_part_2_mf
Thanks for sharing!
Is she okay with taking my $40?
Wow that was a great story. Any other encounters from this?
she sounds gorgeous.