Helping a Family

Well it was a Tuesday, a new day and my phone pinged that was on the dresser next to the bed, but I couldn’t look at it as I was on all fours getting pounded from behind from my current client, this was an overnighter and he wanted one last use of me, which is fine as he’s paying for my time. He had hold of my hips and was thrusting deep into me, his balls slapping my pussy with each thrust. It wasn’t long before he was groaning and filling up the condom, I could feel the warmth from his jizz in the condom in my pussy. He was not getting the bareback treatment as he was a new client and had not been checked out. Only well known clients are allowed bareback.

He finished unloading his nuts and pulled out and lay on the bed, I lay next to him and kissed him, which he liked.

“Mmm, I needed that, thank you for a wonderful evening”, he said, he leaned over kissed me and kissed each tit in turn, got up and went to the bathroom and got cleaned up. I jumped in the shower to freshen up for the day, my client joined me and we smiled at each other and washed each other. We finished up, I packed all my things and dried my hair and said to my client.

“Thank you, you were lovely, a gentlemen” , he came over and hugged me and said “Thank you again for last night, I really did need the unwinding, I’ll sort out payment shortly”, we said our goodbye’s and I left, got in my car and headed home. As I arrived home I checked my phone and indeed the client had paid in full $5000 for an overnighter, not bad for a nights work. I also had another booking it was for another overnighter starting tomorrow at a local hotel for a guy called Dale, age 51, I accepted the booking and checked out his photo, he looked quite handsome for an older guy.

I went in and dropped my bag by the door and went into the kitchen and fixed some breakfast, pancakes are my favourite, just as I was cooking , there was knock at the door and I could see it was my bestie neighbour Carmen, I waved my hand to say come in and she did.

“Morning, girlfriend”, she came over and gave me a hug and a kiss on the cheek.

“Morning gorgeous, want some breakfast?”, I asked her, to which she nodded her head, so I put out 2 plates each loaded with a couple of pancakes, fresh coffee and sauces, we sat and ate and had a catch-up, Carmen had just finished a weekender and was chilling today, she’s been a professional whore like me now for about 6 months now since I introduced her to the life and she loves it, she’s cleared all her debts and her bank balance and wardrobe are looking pretty good now. We chatted about what we had been upto and what we had planned, my day was basically going over my finances and property. We chatted for a little longer over some more coffee and she slurped her last drop of coffee and gave me a hug and left.

I cleaned up from breakfast and switched on my laptop and started checking my finances, my last property had just sold and all the money had come through, not bad profit from it to, bought it from the bank, but needed modernising for $250k , spent another $70k on doing it up including labour , new everything, Bill and his team as always do a fabulous job and I sold it for $400k, a nice profit of $80k, I paid Bill his 10% bonus as agreed, so I walked away with a nice $72k in profit. I already had put in a bid on my next house another fixer upper and that had been accepted, which was great. I texted Bill and gave him the address for our next job and he would go over and see what he thinks on what needs doing. I trust Bill implicitly as he’s never let me down and he knew I’d keep him in business.

Now that all my finances had been sorted and everything attended too, I thought I’d just chill today as no other appointment to fulfil. Just then my phone pinged it was Philip, my very first client and we had become good friends since then, his text said that my appointment for tomorrow was a good friend of his and could I give him special treatment as he’s going through some tough times and it was his recommendation that he see’s me. I replied back and said it would be my pleasure, with a few kisses on the end.

The next day came and I got ready for my appointment, packed my usual gear, I put on some stocking and suspenders, no panties, love being commando, a cup less bra with supports, shortish black skirt and a button up jacket, showing my cleavage off a little and red slutty lipstick. I set off to the hotel and soon arrived, made my way upstairs to the room no on the booking details and knocked on the door. After a few moments an older grey haired guy answered the door, it was Dale, quite handsome, swept back hair, clean shaven.

“Please come in, you must be Cheryl, pleased to meet you, can I take your bag for you” he said in a welcoming tone.

“Pleased to meet you Dale, why thank you” and I offered him my bag, I went in and the room which was fabulous , very spacious, big bed in one room and a lounge in the other. He gestured for me to sit on the couch and offered me a drink , he had a selection of drinks and I asked for a bourbon, and he quickly handed me a glass, I could see he was a little nervous and he poured himself a drink and sat next to me and we chatted for a while.

“I’ll be honest with you, I’ve only used Escorts a couple of times, but Phillip highly recommends you” he said with a nervous smile.

“You don’t have to be ashamed of this at all, we’re just 2 adults going to enjoy each others company” I said to him. He smiled.

I drank my bourbon and got up and went over to my bag and leaned right over to expose my pussy to Dale, pretending I needed to check something in my bag, I could tell he was looking and he was shuffling in his seat, no doubt getting a stiffy looking at my pussy and adjusting his trousers. I turned around and walked over to him and stopped in front of him and took off my top to expose my tits, he was looking at them each in turn, then off came my skirt and it dropped to floor, I was pretty much naked at this point. I straddled Dale and began to kiss him, his hands went round my waist and onto my ass, a cheek in each hand, his fingers began to probe my ass and slit, his fingers running up between my cheeks.

I unbuttoned his shirt and removed it, he was fairly smooth with a little hair, just the way I like it, I really don’t like guys with gorilla type hair, quite off putting. I took off my bra and he began to gently suck each tit, sucking and licking the nipples, he certainly was hard at this point judging by the bulge in his trousers. I stopped him sucking my tits and knelt between his legs and began to unbutton his trousers and pull down his zipper, Dale watched knowing what might be coming, he seemed a little less nervous now, which was good, I pulled off his trousers and he certainly was large in the cock department, he had a huge bulge in his briefs, then off came the briefs and out popped a huge thick cock, he must have been 8” and quite thick.

I grabbed hold of his cock, looked at him and told him to put his head back, closed his eyes and enjoy what I’m about to do, to which he complied. I stroked his cock slowly, gazing at this very nice cock I had in my hand, clean shaven all over, even his ball sack. I began by kissing his rod, working my way up from his nuts to his tip and back down, then running my tongue up his shaft, back down to his balls, I then sucked his nuts, gently but firmly. He was groaning heavily at this point. I opened my mouth, wrapped my lips round this thick shaft and slowly swallowed as much as I could, I had a good 6.5” in my mouth. Good job I can control my gag reflex. Dale let out a loud groan as I swallowed his meat.

I began working his rod, giving him a slow wet blowjob, all the while Dale was groaning and his body twitching. He was close to shooting his wad down my throat a few times, but I stopped, then carried on, by edging him I’d get a large load from him later. After about 30 minutes, I gave him a big passionate kiss, whilst slowly wanking him off, I stood up, cock still in hand and proceeded to walk to the bed, pulling on his cock, Dale soon got up and followed me, he had **** really. I lay on the bed on my back and spread my legs so he could see my wet pussy.

He got on the bed and began to kiss my inner thighs and worked his way to my pussy, his tongue began lapping up my juices, probing my hole deeply , his hands grabbed hold of my tits and began to pinch them softly, rubbing them between his fingers, he began to kiss my stomach, then each tit and nipple, then kissed me, I guided his cock to my snatch and he pushed his tip in, and I groaned as I was about to be impaled by this gorgeous cock, with one slow thrust he sank into me up to his balls. I groaned loudly and I felt very full. I wrapped my legs around his bum and my arms around his head. He began to slowly fuck me, kissing me all the time, he was a very tender, loving and passionate lover.

He fucked me for ages, he was loving that it was a tight hole, he certainly was enjoying it from the kissing and groaning he was doing, I began to talk dirty in his ear.

“You like that tight hole don’t you, is it nice and tight, come on dirty bastard fill me up with your hot cum, I want you to fuck my pussy, feel it gripping your hard cock” with lots of other filthy talk. It didn’t take long and he began to twitch and he groaned loudly as he began to flood my pussy with hot nut juice, I felt each hard spurt, filling my pussy. He pushed deep into me as he came, he just kept cumming and cumming, I wasn’t sure how much more I would get before it began to seep out of me. It wasn’t long before he stopped and lay on top of me, panting heavily, he kissed me and pulled out, as he lay on his back, I got up and began to lick his cock clean, working on the tip first as this is always sensitive after cumming, he body twitched with each flick of my tongue.

“Christ, you’re filthy” he said I licked his shaft, lapping up the cum and juices, once I finished I lay next to him and we snuggled.

“I thought you’d like that” I said to him, we snuggled for a bit and I got up as cum was flooding out of my pussy, I went into the bathroom and cleaned up, when i walked back into the room, Dale had put on the TV and was watching a movie that was on. I lay next to him and we chatted.

“I rarely use Escort services, I’ve had a few affairs/girlfriends, but they all turn out to be very needy, I am married as you know, but my wife to be honest is a fucking bitch, we haven’t had sex for years now, hence why I’ve gone elsewhere. I can’t leave the bitch as she would suck me dry for everything I have. I’ve not spent all this time building myself up for her to come and just take it all, as she has had no interest in my business”

“Since we had our son, she went cold, and she absolutely smothers him, he can barely do anything without her interfering and meddling, he has little friends and he’s never had a girlfriend as the bitch scares them off and is nasty to them, the amount of arguments we’ve had over him is unreal”.

“She doesn’t sound pleasant at all” I said, I could see that he was not happy about his wife and he certainly felt trapped, a story I’ve heard from many clients, hence why they use our services. We lay in bed naked, his cock was semi stiff again, so I caressed his cock as we watched, we touched each other , just fumbling about, as we would have plenty of time to empty his balls again and maybe a third time. It was getting late in the afternoon and Dale said, what would you like to eat as I’ll order some room service. I asked for my favourite, Steak, medium rare with lots of veggies, Dale picked up the phone, dialled room service and ordered 2 steaks with veggies.

“Would you like a drink, while we wait for our food” he asked.

“Oh yes, Bourbon again please”, he handed me a large glass full of the lovely stuff and i began to sip it. After a while, there was a knock at the door, , Dale put on a bathrobe and closed the bedroom door as I was lay naked on it, didn’t want to the water to see me in the buff. I heard Dale thank the waiter and I heard the door close and I peeked round the door, the coast was clear, I took off my robe as I think Dale liked me being naked and sat at the table and we ate our food and drank. Dale kept looking me over and had a smile on his face. We made chit chat, he began to explain a little more about his son and I had an idea, which I would discuss with him later on.

Once our food had gone down, I got up and walked round to Dale and leaned over, my boobs in his face, i reached down and grabbed his semi hard cock and began to wank him off in short fast bursts, he groaned as he was getting a fast hand job.

“Don’t you dare cum, Dale”, I said to him and he nodded as he barely able to speak with the fast wanking spurts he was getting. I kissed him as i did this and his hand cupped my ass cheek and a finger began to probe my asshole.

“Oh you want that hole don’t you”, I said to him and he again nodded, I pulled his finger from between my ass cheeks as they had not slipped up my ass yet and sucked his finger, making it wet with saliva, I stopped sucking his finger, and spat a little on my finger and rubbed my asshole.

“OK, you can finger my ass now”, he slipped in his finger up to his knuckle and began to finger fuck my back passage. I groaned like a good whore, his cock was very hard now and his balls were again swollen, full of tasty, juicy cum. I stopped wanking his cock, walked over to the bed, lay on my front and stuck my ass in the air and pulled my cheeks apart, Dale got up and came behind me, me could see my wet pussy, still oozing cum from before and my butthole, slightly gaped.

He touched and squeezed my ass cheeks, rubbing my pussy, fingering me, one finger, then two, I was moaning at the attention. I then felt his tip rubbing my clit up and down, my pussy was soaked at this point, then then rubbed my asshole with his tip, lubing it up , I felt more spit go on my asshole and he then slowly began to push his rod up my ass, I let out a big groan as this was one of the biggest cocks I’ve had up my ass. Dale was careful not to push to quickly as he knew it would hurt me, so he gently pushed in and out, easing more cock up with each thrust.

It wasn’t long before he was balls deep , his balls resting on my ass cheeks, he lay on top of me and I turned my head and we kissed, lots of tongue, he was horny, he mentioned earlier he had not had anal for years, so I was giving him a treat. He began to thrust his cock , slowly fucking me. I gasped with each thrust, his balls slapping my cheeks. Dale fucked me like for a while, and then turned me over while still impaling me, so I was now on top, I positioned myself and began to slide my ass up and down his cock, one hand cupped my tit and the other, he stuck two fingers up my pussy, both of us groaning and panting. I began to ride his cock hard and fast as my ass was accustomed to it now, Dale grabbed my hips and I rode him and he began to jerk and I felt hot spurts of creamy goodness hit the inside of my ass, I grabbed his balls and squeezed them as he came, I wanted to make sure he gave me a big load.

Dale certainly gave me a big load, coating the inside of my rectum with his creamy nut juice, once he stopped , I lay back on him, both his hands cupping my breasts, pinching the nipples, i turned my head and we kissed. He was panting, out of breath, i lifted my ass of his still erect cock and immediately wrapped my mouth round his rod and licked all the juices off his shaft, he groaned as I swallowed his manhood, I squeezed the last drops of cum out of him, his cock was not for going down, so I began to wank him slow and fast, Dale began to groan loudly, his body twitching with each thrust of my hand, I flicked my tongue on his tip, precum coated the tip, it tasted very sweet.

I stroked his cock for about 5-10 minutes and he began to groan and tense , he was going to cum again, so I wrapped my mouth round his cock and began sucking hard and deep and within seconds I got what I wanted, spurts of hot man juice, as he came, he put his hand on my head , thrusting his cock deeper into my mouth and I groaned as I got another load, not big, but enough. I didn’t let one drop come out of my mouth, once he stopped I swallowed every drop and carried on sucking. I wanted every drop as I was very horny now, he had given me a load in each hole, which is what turns me on the most. Once I had every drop, I lay next to him.

“Fucking hell, I haven’t done that since I was at college , you are one dirty girl”, Dale said with a huge grin on his face. I kissed him.

“I aim to please, you were fantastic, you have a gorgeous cock, If I was your wife, I’d be riding that rod every night, you certainly know how to use it, you’re wife is certainly missing out” I said to him, he smiled and we hugged.

“Well, she’s fucking someone else anyway, so fuck her, she’s a horrible person, can I trust you, Philip vouched for you” He asked.

“Of course, anything you tell me is private and stays private” I responded.

“Well, Philip is helping me divorce that leech of a wife of mine, and ensuring she doesn’t get a penny. I was a wealthy man before we met and all she has done is spend my money, she made sure we had a kid, I really didn’t want one, but after Tim was born, I actually liked being a Dad, but she is an interfering bitch, she controls everything with him. The amount of fights we’ve had over him is unreal.

I try and make sure he has a good life, but she won’t even let him have girlfriends, she chases them away, I’m sure he’s still a virgin and he’s 21 for fucks sake, he’s a good kid and quite good looking, but has very little social life, spends most of his time on his computer because of that bitch.”

“That’s so sad, poor kid, stuck between two very opposite parents, you, the loving Dad and the uncaring Mother”, I said and gave him another hug, I could see he was very torn and troubled, he was a nice guy stuck in a bad place right now.

“Yea, well that bitch is apparently going on holiday with the ‘Girls’, more like with her fuck buddy, good, got two weeks of peace and she’ll be out of the country, I’m sending Tim to our Villa for a week which he loves, he’s never been alone as she always goes with him and it will do him good.”, he said and just then he got this light bulb expression on his face and then he asked me this.

“How would you like a Holiday, all expenses paid and of course your usual fee for a weekend, I could rent the villa next to ours and you have fun with my son, would you be up for that, could you bring him out of his shell as he’s very shy, i know it’s a bit of an odd request, but I think would boost his confidence immensely, what do you say”. He said with a huge grin on his face.

I thought about it for a minute and said “Fuck it, why not, I’d be glad to help”, I wanted to help Dale out as he was a really nice guy, hell I’d love to have a guy like him, but who knows, especially with a big cock like his. I’m sure I’ll find my prince charming one day as long as he didn’t mind me being a slut for hire in my past.

“Great, I’ll set it up” and we discussed the dates and he requested my booking through the agency, to which I confirmed straight away. I do like helping people and I love sex, so a win for both sides i thought. It was getting late and we just snuggled up in bed totally naked and we watched a trashy action movie, once it finished we fell asleep, Dale spooned me, one hand on my tit and his cock resting between my ass cheeks, which felt quite nice, he had given me three loads now, so I was going to let him sleep and gather his strength for the morning, he’ll need it.

I woke reasonably early and heard Dale speaking to someone, I grabbed a robe and went to see what was going on, Dale was closing the door and I saw that it was actually our breakfast being delivered, I could smell the coffee which is always nice first thing in a morning. Dale turned round and saw me standing there.

“Morning, sleepy head, I wasn’t sure what you like for breakfast so I ordered a full English breakfast with some continental goodies too”, He said and came over and gave me a hug and a kiss. I sat down and he asked what I like, Full English I thought for a change, and he dished that up for me and poured me some hot coffee. We sat and ate, I stretched my foot out to his crotch and rubbed his cock through his robe, he was already semi hard.

“Someone’s in a good mood I see”, I said with a dirty grin on my face.

“Of course, hard not too when you look like you and you’re so filthy in the sack, what’s not to like” He said smiling like a big kid. We ate our breakfast, and chatted about the plans for his son, it felt a bit off talking to a Dad arranging a fuck session for his kid, but i was helping this kid out. We chatted for ages, letting our breakfast go down with a few cups of coffee. I rubbed his cock with my foot and he was certainly hard now and I used my foot to expose his cock, I liked looking at his cock, it was a magnificent specimen, 8”long, wide girth, shaved shaft and balls, his balls were nice and full again.

“OK, start wanking yourself”, I said to him and I opened my legs and showed him my wet pussy and I began to stroke my clit. He grabbed hold of his cock and began to slowly wank in front of me, I watched his cock, and it didn’t take long for his tip to be covered in precum, which I love the taste of. I told him to stand up, which he did and I came over and kneeled in front of him, still wanking his cock and watching this juicy fat cock in front of my face, the tip glistening with precum, I flicked my tongue on his tip and he groaned. I cupped his balls with my hand and wrapped my lips round his cock and he let go and used my other hand to grid his shaft firmly and I began to blow him deep and hard.

He put both hands on my head and started to mouth fuck me slightly, groaning as this hot slut was gorging herself on his cock, it wasn’t long before he began to tense, as he was about to cum, I pulled away from his cock, opened my mouth and wanked him fast and I got hot spurts of cum all over my face, cheeks, nose and some in my mouth. Dale was groaning, his body twitching with each spurt, once he stopped I sucked his cock some more. I wasn’t finished there, I began to wank him hard and fast again, I grabbed his balls tightly with one hand. I looked at him, my face covered in his cum and licked my lips.

“Oh, you fucking dirty slut, god you’re great, want some more do you??”, he said and I nodded with my mouth open, tongue out to hopefully receive another load. He grabbed hold of his cock and began to wank himself off, it didn’t take long for more spurts of hit cum to splash across my face, Dale aimed everywhere but my mouth, he wanted me coated in his nut juice, his warm cum was running down my face onto my tits now, I was absolutely drenched, but I didn’t mind, Dale thoroughly enjoyed it, don’t think he’s had a slut like me before. I do aim to please my clients though and I love a warm facial.

I leaned back and rubbed the cum into my nipples, Dale sat down and watched me pleasure myself, I scooped some cum onto my fingers and rubbed it into my clit and it didn’t take long for me to orgasm which was quite hard. Once I finished having my orgasm, i scooped all his cum off my face into my mouth and swallowed every drop I could get, i got off my knees and headed for the shower, Dale was right behind me. We washed each other’s bodies, I gave his cock and balls a good wash which he enjoyed and he washed all my boobs, ass and pussy, his hands were all over me really.

I stepped out of the shower, got dry and gathered my things, ready to leave. I walked over to Dale who was still in his bathrobe, put my arms around him and gave his a long lingering kiss. I had once last feel of his gorgeous cock and said.

“Thank you for a wonderful night, you were fantastic, your cock is gorgeous, could play with that for hours” I said with a lustful smile on my face.

“Thanks, you were amazing also, I needed everything we did, it took the stress out of me for a while at least.” Dale replied.

I picked up my bag and left the hotel and went home, I had no further appointments today, so I could catch up with paperwork and my house projects. A little later that morning, my phone pinged twice, once from agency app and the other from my bank, Dale had confirmed the appointment for last night, so the agency released the funds. Now I was just waiting for my next appointment. I was also going over n my head on what to do with Dale’s son, but that is another story.