Tara had been having money issues for the better part of a year now. Struggling to keep a job while raising a son on her own was really taking it's toll on her. She had just received a letter from her building manager informing her that rent was increasing again (second time in two years), and that if she couldn't pay off what she owed, she would be out on her ass in a few months.
She took to facebook to air her problems, hoping a friend would come through with some part-time work she could pick up to make ends meet. As the weeks went by and Tara got more desperate, She began to consider applying at strip-clubs as a server, dropping resumes off at hooters and other local sports bars in the hopes of finding something. A month and a half had passed, and she was still searching for work. She posted again about needing $500 dollars by the end of the month or she would be homeless. A real sob story by any account, but I knew the time was right. She was desperate enough.
I sent her a text, asking if she wanted to go out for dinner to unwind. My treat, of course. She jumped at the opportunity to have something other than macaroni and cheese for dinner. She came over to my condo, I ordered in pizza and salad from a local restaurant she loves. The conversation was just small-talk at first, how's the family, etc. After a while I asked about work, knowing she would tell me about her money woes.
I said to her "You know, I've got some extra cash kicking around, and I'd love to help you out. We've known each other for years, It's the least I could do." Her eyes lit up as she sat up straight. "Really? You would do that? I don't even know what to say…" She trailed off, excitement in her voice.
"Well, see, I'm not just going to give you the money.. I need something from you, Tara." The blood was pumping through my veins, I could feel my cock growing in my pants. "You see, I've wanted you for a long, long time." I stood up, the outline of my erection clearly visible.
The look on her face changed from excitement to shock, as she noticed my bulging dick. "Whoa, Sam, you're a nice guy and all.. But I'm not some slut you can just pay to blow you.." Her breath had quickened, She seemed tense, worried. "You need to relax, Tara. You've told me before you enjoy giving head, so what's the big deal? You'll get to keep your apartment, Your son will have somewhere to sleep.."
She sagged visibly when I mentioned her son. She took a deep breath, wiped the tear from her cheek and said "Fine. What do I have to do?" I unzipped my pants, revealing the now fully erect cock stuffed inside briefs. I told her to take my pants down, and she did so with trembling hands. my dick leaned towards her, she seemed startled by it's full size. She placed one hand on the base, gripping the shaft and inspecting the shave-job. I groped her tits with one hand, and placed the other on the back of her head. I grabbed her hair, bent over and positioned her to look me in the eyes. "Use your teeth and you'll regret it…" She nodded in understanding, still too stunned to say anything.
I slapped the head of my dick against her tongue a few times, and then began penetrating her mouth. I went slowly at first, gauging how deep I could go before she gagged. As i felt her relaxing, I started fucking her throat deeper and deeper with each thrust. After a few minutes, I had 7" of rock-hard dick in the back of her mouth.
The mix of pre-cum and drool dripped off her chin, and between her big tits. I could feel her struggling to catch her breath between each thrust, and her face was turning red. I held her head with both hands, and retracted my dick from her mouth completely. She gasped for air as her spit slid off my dick, making a further mess of her top. Tears were still streaming from her eyes as I grabbed her hair and made her face the ceiling. I didn't have to say anything, and she started licking and sucking my balls.
I took my free hand and started masturbating. The sensation of having my balls sucked while rubbing my head was enough to get tons of pre-cum out, so much so that I was over-lubed with it. I looked at my hand, small white ropes between my fingers, and wiped it on the side of her face.
My god she was mad. She pulled herself away and gave me this look of utter disgust. "Did you just wipe cum on my face? I can't believe you did that. I thought you were gonna cum in my mouth, you never said ANYTHING about my face!!". At this point, a big grin crossed my face.
"Tara, I haven't cum yet… that's just a preview. Now, about this facial business.. You'd look great wearing my cum, how much extra is it gonna take? $50? $100?"
"You don't get it, I've never had someone cum on me. Not my ex-husband, no one."
"Oh, you'll love this. A hot, sticky mess all over your glasses, forehead and cheeks!"
I could tell she didn't want it, but I didn't care. Tonight, she was my slut. I put my dick back in her mouth, and began thrusting away, really going balls deep. I face-fucked her harder than I've ever in my life, with anyone. I tried to time my orgasm with her need for air, and it was damn close. I could feel my head swelling, the pressure in my balls rising. "this is it" i thought to myself. She pushed herself off my legs with her hands, her eyes bloodshot and tearful, and gasped for air. I grabbed her hair, positioned her face, and within five strokes…
Oh god. OH GOD. cum everywhere. The first shot runs up her cheek, over her left lens, up her forehead and into her hair. the second runs across her nose, on the right lens, into her hair and onto the floor. the last few spurts hit her lips and chin, running down into the fine mess that was her cleavage. I sat back into a chair, totally content. Before I could say anything she had ran to the bathroom to clean up.
She came out about 10 minutes later, still looking really unhappy. Shellshocked, almost. I handed her the envelope with the money, grabbed her coat, and thanked her for her service. I told her if she ever needed more money… just ask ;)
Source: reddit.com/r/sexystories/comments/2ok0a9/desperate_times_call_for_desperate_measures
Awesome story, hope to see more of her! :D
Pretty good but for some of us a bit more buildup is like foreplay And makes it that much more enjoyable