Money Well Spent

Info GWinterbourne
07 Aug. '18

“Hi, I’m Sean,” he said as he stepped out of the car. He had pulled around to the back of the house, as I had requested, and I was meeting him at the garage door, out of the sight lines of any nosy neighbors. “You must be...”

“Maggie,” I said quickly. “Just call me Maggie.” Maggie was the pseudonym I had chosen for this encounter. Not my real name, but close enough. I assumed “Sean” wasn’t really a Sean either.

I tried to decide what his real name probably was. Mark, maybe. Possibly Dan. Something monosyllabic and masculine. He was tall, with dark brown hair, hazel eyes, and an athletic build. He was also incredibly handsome, with a smile that lit up his face. The clincher for me—his shirt sleeves were rolled up to reveal strong forearms and a watch around his left wrist. I had weakness for men in dress shirts with turned-up sleeves. To me, it represented the best of both worlds. Here was an educated man who wasn’t afraid to get his hands dirty when needed. 

“I guess you should come in,” I said, rather stupidly, after staring at him for a tick too long. I quickly ushered Sean through the garage and into the house, where we found ourselves in the kitchen. “Um, how does this work? Do we just get started? The lady on the phone said to give you half upfront, and half when you leave.” I reached for my purse, which was lying on the kitchen table. 

“Slow down, Maggie,” Sean chuckled, as he set down his messenger bag next to my purse. “I like to take my time and get to know you before we start. The clock doesn’t start until you’re sure you’re ready. Is there somewhere where we can sit and talk?”

I nodded toward the living room. “Sit wherever you’d like. Can I get you anything?” 

“A glass of water would be great. Thanks.”

As I grabbed a glass from the cupboard, I took a moment to try and compose myself. I had spent all morning carefully choosing my clothes, applying my makeup, and attempting to style my unruly hair. My heart was pounding with anxiety over whether I had achieved my goal—appearing sexy, not slutty—when the reality of how ridiculous I was dawned on me. “What man would get himself gussied up for a prostitute?” I thought to myself. Because that was what Sean was. The agency who sent him had called him a “companion,” but I might as well have gone trolling for him on a street corner. I wasn’t seducing anyone this afternoon. It was a foregone conclusion that Sean and were going to have sex—and that I was going to pay him. 

Thoroughly dispirited by the trajectory my life had taken, I filled the glass with ice and water, carried it to the living room, and handed it to Sean. He was sitting on the couch, and he patted the cushion beside him. “Come and sit next to me.”

I sat down as far as I possibly could from him and still occupy the same piece of furniture. “Come closer,” he said, “I don’t bite—unless you’re into that.”

I must have blanched, because he quickly said, “Hey...just a joke. Relax. Thanks for the water, by the way. It really hit the spot. You look like you could use something stiffer, though.”

“Yeah, a good stiff dick,” I thought to myself. “I thought that’s why you were here.”

Sean reached down the couch and took one of my hands in his. “Come closer,” he said again, “and tell me why I’m here this afternoon.”

I scooted down the couch, nearer to him, but still not touching. “I don’t know why you’re here,” I said. “I guess I’m just frustrated.”

“Frustrated with what?” he asked gently.

“Everything.” Once I had admitted it, it all just came pouring out. “I’m frustrated that I’m a writer, and I work from home and don’t see another living soul all day. I’m frustrated that I’m in my forties and have never had an orgasm I haven’t given myself. I’m frustrated that my husband doesn’t seem to care. I’m frustrated that when he comes home at night, he’d rather eat and drink and eat himself into an early grave rather than touch me in any meaningful way. And I’m frustrated that when he does decide to touch me, he can’t get it hard enough to even complete the act anymore. I haven’t had a good, hard prick in years.” The weight of what I just said hit me suddenly, and I began to cry.

“Hey, hey. Don’t cry, love. That’s why I’m here. You are a beautiful woman, and you deserve to treated as such. We’ll do what you want, at the pace you want. By the time I leave, I guarantee I will have given you an orgasm or you don’t need to give me the second half of the payment.” He stroked my cheek, and brushed away a tear. “What do you say? Do you want to give this a go?”

I nodded. I got up from the couch and went to the kitchen to retrieve my purse. I took $250 in cash from my wallet, and silently handed it to Sean. “Let’s get started.”

“Perfect. I was hoping you’d say that,” he said, stuffing the money into his wallet and rising from the couch. “Where are we going?”

“Upstairs, I guess.” 

As we passed back through the kitchen on the way to the staircase, Sean paused to pick up his messenger bag. “Never know what might come in handy,” he said with a wink.

I led him up the stairs and down the hallway toward the bedroom. Along the way, I closed the door to my daughter’s room as if to shield her sanctuary from my transgressions. 

When we reached my bedroom, I led Sean inside and closed the door even though we were the only people in the house. I started to remove my blouse so we could get down to business before he quickly stopped me. “Easy. We have plenty of time. Plus, I’d like to be the one who undresses you, if that’s alright.” I nodded my assent.

“But first,” he said, “I’d really like to kiss you. Would you like that?”

I knew he was just playing the role I had paid him to play, but something in his voice made me weak in the knees. It had been so long since a man had been interested in my body that I had almost forgotten what it felt like. “Yes,” I whispered. “I would like you to kiss me.”

Sean bent down and took my face in his hands. “You’re really beautiful, you know.” His voice was breathy as he leaned in for the kiss. 

As soon as his kiss landed on my lips, it cascaded through my body, pooling in the spot where all good kisses eventually land. My lips opened to his, and his tongue began exploring my mouth, as his hands began their own journey around my body. One hand cradled the back of my head, while he used the other to trace down my body, from the hollow of my neck to my breast, where it lingered, teasing my nipple through my bra, and giving me sensations between my legs I hadn’t felt in a very long time.

Once Sean was done with my mouth, he moved on to my neck, alternating between kissing my collarbone and whispering in my ear, “God, you’re sexy. I want to fuck you so bad.”

I responded by turning his mouth back to mine and kissing him hard. “And I want you to fuck me.”

He unbuttoned my blouse, and slid it off my shoulders. He opened the clasp on my bra with ease, and I leaned forward to let my small breasts fall into his waiting hands. “Sorry there’s not more there to work with,” I said. 

“Nonsense. You know what they say—more than a handful...” He used his thumbs to massage my nipples before lowering his head and taking one in his mouth. His sucking opened a floodgate in my pussy, and I could feel my panties and jeans become wet with my desire for him.

As if he knew the effect he was having, he unfastened my belt and unzipped my jeans. He pulled them down, and I stepped out of them, so I was standing almost naked, wearing just my underwear. He slipped one hand down the front and felt between my thighs. “I don’t think we’ll be needing the lube I brought.”

“I’m sorry. I’m not usually so...” I paused, trying to think of an appropriate word, then settled for the obvious, “...wet.”

“Are you kidding me? I love it,” Sean said. “If I ask how I’m doing, 99 times out of 100, you’ll just say ‘fine’ whether or not it’s the truth. But your body doesn’t lie, Maggie. I can feel what I’m doing is working. Come on now, and help me out of my clothes.”

I slowly unbuttoned his shirt, and couldn’t keep myself from running my hands gently over his well-defined pecs and washboard stomach. “It’s so nice not to have a beer gut staring back at me,” I said.

“Take off my pants, baby. I have a present for you.” 

As I unfastened his belt, I felt his cock surge. I have to admit that I was curious about what I had paid for. I hurriedly undid the button and unzipped him, easing his pants down his hips so he could kick them away. Left with just his boxer briefs between me and my prize, he said, “Go ahead. Take a peek.”

I pulled the waistband of his briefs down and was rewarded with a glimpse of the most massive dick I had ever seen, and he wasn’t even fully erect. “I hope you don’t mind that I’m uncut. My family emigrated from Ireland when I was a kid, so I never got circumcised.” 

Having never seen an intact penis in the wild, I was mesmerized. “Go ahead and touch it,” Sean said. “It just has an extra layer of enjoyment for you.”

I reached down with both my hands and slid them up along his shaft, and then back down, pulling back the foreskin, and exposing the swollen head. Sean drew in his breath, and I was rewarded with the emergence of the first drop of pre-cum. “See,” he said, “nothing to be afraid of.”

“I don’t know about that. I assume it’s only going to get bigger,” I said, cautiously. “I don’t know where we’re going to put all that.”

“Don’t you worry. I have a feeling you can take much more than you think you can. But that comes later.”

He sat down on the bed, and beckoned for me to join him. He pulled me over, and eased my panties down my hips. Then he turned me around so I was sitting in his lap, and somehow shifted both of us onto the bed, where I found myself lying between his legs. 

“Show me how you touch yourself,” he whispered. 

“Wait a minute,” I thought. “I’m not paying you to watch me do something I can do myself for free.”

“Show me,” he said again. “I want to see what feels good to you.”

Feeling terribly self-conscious, I nevertheless followed his instruction and reached between my legs to begin stroking my clit in a slow, clockwise pattern. As I stroked, Sean began to kiss my neck and caress my breasts with his hands. “Oh, Maggie, you’re making me so hot,” he moaned.

I continued to fondle myself, and soon, I felt his hand engulf mine as he followed my motions. He used his left hand to pull mine out from under his right, allowing him to take over for me, matching the speed and intensity of my strokes exactly.

The weight and warmth of his much larger hand intensified my pleasure immensely. Several times, he brought me to the brink, then eased me back again, only to build to the inevitable. I could feel that Sean now had a respectable erection pressing against the small of my back, and the knowledge I was turning him on sent me over the edge toward the most intense climax I had ever experienced, and the only one I hadn’t administered myself. As I lay there, pressing my pussy against his hand to extend my orgasm as long as I could, all I could think of to say was, “Well, I guess you get the rest of your payment.”

“Shh, Maggie. Let’s not think about that now. We still have a lot of time left, and I want to see what else I can do for you.” He pulled himself out from under me, and leaned over to give me a kiss. “Do you like to have your pussy licked?”

I nodded. It had been forever, but I thought maybe, just maybe, I remembered.

“Then let’s get you down to the end of the bed so I can work my magic.” He shifted me to the edge of the bed, then positioned himself on the floor between my legs. Running a hand down the inside of each thigh, he spread me open, and began to lap at my pussy, alternating between pushing his tongue into me as deeply as he could and licking and sucking my clit. I felt myself begin to flow again, and evidently so did Sean, because he moved his mouth down to stem the tide. “You taste so good.”

I was getting so close to my second orgasm of the afternoon that I could have killed him when he stopped suddenly. “Maggie, do you know where your g-spot is?”

“I wasn’t aware I possessed one. At least no one has ever gone looking for it.”

“That’s a shame. Every woman has one. It just takes more effort to find it on some women than it does for others. We’re going to find yours. Can I put my finger inside you?”

“Sure, but I wish you’d go back to eating me out.”

“All in good time, love. All in good time.”

Sean inserted his finger into me and began stroking the top wall of my vagina. Although he also kept his thumb on my clit and was gently stimulating me, I was about to ask him to give up when suddenly he found what he was looking for. I jumped, then pressed my pussy against his hand. He smiled. “Got it.”

He withdrew his finger, and I was about to protest when he pushed three fingers into me and rubbed them against my newly discovered g-spot. Then he lowered his head, and resumed sucking on my clit. With both internal and external stimulation, I couldn’t help but climax quickly, and hard. I held his head against my pussy until I was done shuddering, savoring every last bit of my orgasm.

“I’ll take it that was good,” he said, when I had freed his head from between my legs.

“I’m sorry. It was just so intense, I couldn’t help myself.”

“No need to apologize. That’s what I’m here for.”

Any fantasy I had concocted about this hot guy wanting me for me evaporated completely. This was, as Sean had just reminded me, a business arrangement. “I guess you’ll be going now,” I said.

“Oh, Maggie, please don’t rush me out the door. Besides, I can’t leave until you help me with this.” With effort, he rose from his knees to reveal that his already massive cock had become fully engorged. I was stunned by, and a little frightened of, the organ bobbing in front of him. The foreskin had retracted to reveal a huge purple knob on the end of a dick pulsing with thick, ropy veins. “I need you, Maggie. I need you like I’ve never needed a woman before.”

I know his words were part of the act, but there was no denying the urgency of his erection. I sat up and reached for him. He was so thick, I wasn’t quite able to get my hand completely around him, so I put my lips on the tip of his prick, rolling my tongue around the head as he moaned. “Oh God, Maggie, that’s so good, but I need to be inside you.”

I’m not sure how, but he bent over and took a condom out of his messenger bag. “Do you want to help me put it on?” he asked.

He tore open the package, and somehow he managed to coax the condom over the head of his enormous member. He pinched the reservoir while I used both hands to ease it down the length of his cock. “Are you ready for me?” he asked.

“I don’t think I’ll ever be ready for that,” I said honestly.

“We’ll take it slow. If it gets too much for you, let me know, but I’m sure you can handle it.” Sean was leaning over me now, his penis grazing my stomach as he spoke. “It helps if you lean back into the pillows and spread your legs as wide as you can.”

I did as I was told, and Sean soon had the tip of his prick positioned to penetrate me. “You’re good and slick, so this should be easy,” he tried to reassure me.

The next instant, he rammed the head of his cock into my pussy. I had never had anything even half as large inside of me before, but I was surprised to find that I liked it. With his next thrust, he had submerged more than half of his dick, and with one more, he was balls-deep inside of me. I could feel how stretched my pussy was, but there was more than enough lubrication left over from our previous adventures to help him move inside of me. As he got into his rhythm, I moved my hips in time with his thrusts.

He supported himself on the forearms I had admired so much earlier. As he stroked, he looked deep into my eyes and said, “Maggie, you are magnificent. Your body is amazing, and I’m lucky I get to have you. Don’t ever think you have to settle for a man who doesn’t appreciate you.” He increased the speed of his thrusts, and with them, the pressure on my already stimulated g-spot. I grabbed his ass, and pulled him even deeper into me, surprised by my ability to not only take his huge cock, but enjoy it, and crave more of it. I felt myself on the brink of yet another orgasm, and I managed to squeeze my hand in between us so I could finger my clit while Sean kept at it. At about the same time I started to come, I felt his balls tense, and knew he was delivering load after load of cum deep inside of me. I could only hope the condom was holding as my own climax washed over me, and Sean collapsed, completely spent.

We remained there together, sweat-drenched and muscles quivering, for quite a while. Sean stroked the side of my face and smiled before seeming to finally remember where he was. Moving quickly, he grabbed the base of his dick and slid his rapidly deflating member out of me. I was astonished to see the condom had survived, but the reservoir had been no match for the volume of cum Sean had deposited. It was already leaking down the sides of the condom and out the base as he pulled away.

“Sorry about that,” he said. “I guess I got a little carried away.”

“Never apologize for what just happened between us,” I said dreamily. I’m not going to be able to walk for a week, but it was worth it.”

“Yes, it was,” Sean agreed. “It was incredible how into that you were.” He glanced at the watch still on his wrist. “Damn. I’m afraid I’m going to have to leave you now,” he said with real regret in his voice.

I understood. I could have cuddled with him until morning, I was in such a blissful state, but my family would be home soon enough, and I was sure Sean had to get to his next client. He had, after all, accomplished what I had paid him to do. As he was dressing, I managed to hobble out of bed and into my robe. I followed him downstairs, and handed him the remaining $250 I owed him.

“You know, Maggie, I’d be happy to come back should you ever need me again.” He leaned down and gave me a long, deep kiss.

“I think my itch has been scratched for the time being,” I said. “Besides, I don’t know if that’s such a good idea. Once we get started, it might be hard to break the habit.”

“You’re probably right. You were amazing though. I’ll think about this afternoon a lot.”

With that, he let himself out through the garage and was gone. I know he was just saying what he thought I wanted to hear, but his words meant a lot to me. And he was the best $500 I ever spent.


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I never do this, but I felt I had to comment. I peruse the stories here to get ideas—what turns women on, how to spice up things in the bedroom—but I think some things in this story could use some clarification.

First of all, “Maggie” is gorgeous. Not in that, “Ooh, look at me” way, but in that enchanting, and oh-so-sexy, “I have no idea how beautiful I really am” way.  I don’t know why Maggie felt she needed to pay for sex. If she walked into any bar in America, she’d have guys lined up out the door waiting to hit on her. But maybe that’s it. She doesn’t want the physical act so much as she wants the emotion that comes with it, and there’s no guarantee that some rando at the bar wouldn’t just use her and walk away. If she pays for the illusion of intimacy, she gets the illusion of intimacy.

But, here’s the thing, her “companion” wasn’t just pretending. Everything she did, from the way she first looked at him, to the way she she touched him, to the way she pulled him inside of her made him fall for her just a little bit more. It may have started out as fucking, but it came to be about making love by the end. Maggie is that most dangerous client—the one that gives you money, but takes your heart.

Maggie, if you’re reading this, your husband is a fool. To miss out on you is criminal. I hope our afternoon together helps you find the confidence to go get a man who treats you the way you deserve to be treated, and who knows just what to do with your body.