The Old Man and the Hooker Sierra

I turned 60 and wanted to treat myself. Don't get me wrong, I'm not an unhappily married man, but after a quarter of a century of marriage, a guy gets restless. My wife had planned on being away on business for a week, so I decided to take advantage of this little window of opportunity and indulge myself for one special night.

I started by looking into escort agencies and found myself browsing online ads for "elite companions" and women who offered "the girlfriend experience." I wasn't a complete stranger to the world of prostitutes. I had partaken of their services while on the road for work, had received a few hand jobs in massage parlors and even got head from a stripper once, but I wanted this time to be different. I wanted someone unlike anyone I'd ever been with before.

I had a decent savings account and made some excuse to withdraw a relatively large sum. I wanted this to be right and I didn't mind paying. After hours and hours of searching lots of undesirable looking tramps and over-the-hill social rejects, I found this one lady who appeared perfect. No tattoos, no ugly piercings, no apparent drug use. She was young, pretty, with a kind smile and a twinkle in her eye, though naturally her face was largely obscured in the pictures.

Although she had quicker, cheaper options, her deluxe package consisted of an evening date, "companionship", a sleepover and then a repeat performance in the morning. All this would cost me a large chunk of change. It was more than I had initially wanted to pay, but after reading several detailed reviews from satisfied customers, I decided this was my girl.

I bought a disposable phone so that the calls wouldn't be traced to me or seen by my wife. I called this girl and when she answered, was very sweet and well-spoken. I told her I wanted to book a night with a stay over and we set up a date, a long way in advance. We agreed that I would call a week ahead to confirm, and then on the day.

On the appointed day, I would call again and we would agree on a location. I still wasn't completely sure if I wanted to rent a room somewhere or host at my house, but I figured I could finalize details later. I knew there might be risks if she came to my place, but I also liked that idea a lot. I wanted an intimate experience, not the usual anonymous transaction I had had while paying for sex and I felt bringing her back to my home might be the answer.

So, as arranged, I called this young lady a week prior to our date. She went by the name "Sierra," a classic prostitute name if ever there was one. In fact, I think that may have been the name of the stripper who sucked my dick that time. I couldn't quite recall. Anyway, Sierra was very sweet, possessing a delightfully youthful, girlish voice and won me over by calling me "baby" and "honey."

This only made me more excited to meet her. The next week was pure torture. I had butterflies in my stomach the entire time, and couldn't stop going online to view her ads, glimpse her pictures and read her reviews.

Three days before, my wife left town as planned, and I kissed her goodbye at the airport. Time dragged on, but eventually the day came. I called Sierra in the morning, but frustratingly I got her answering machine and left a message. Three painful hours went by. Finally, my phone rang and I quickly answered, knowing it had to be her. I loved hearing her voice on the other end.

"Hi baby. Are you ready for our date tonight?" she purred.

Oh yes, I was. I wanted to take her out to dinner first and I gave her the address of a place that I had picked out. I had driven around the last few days looking for the perfect place; intimate, out of the way, secluded.

Somewhere where we wouldn't be spotted and where I could reserve a romantic booth with low lighting. We set up the time for 7 o'clock and she sounded excited to meet me. Of course I arrived far too early.

I told her I would be seated at the bar and I just sat there, my stomach in knots, watching the door. I didn't order a drink yet. I had told my wife that I would be at a movie that evening and then would get an early night, so would be out of touch. I didn't turn my phone off, but just prayed she didn't call with some kind of emergency. The minutes slowly ticked by and I started to feel sick with nerves. It was 7:05 and she wasn't there. The door would open, my heart would leap but it would be someone else.

At 7:15, she walked in. She looked incredible. She was everything I could ever have dreamed of and more, physically anyway. She was in a long black dress with enough leg and chest revealed to be perfectly alluring without being slutty. She looked over at me and I gave her a nod and a tiny wave. She walked over and said "Dave?" softly. She was exquisite. I couldn't really speak and just nodded, feeling totally self-conscious.

I felt myself go bright red, imagining that I looked like an old, pathetic fool. But I wasn't bad looking, I was dressed nicely, I still had my hair and a decent body, so didn't think she would be disgusted by me. She leaned over and gave me a kiss on the cheek and then whispered in my ear "Hi Dave."

My heart skipped a beat. I looked at her. She had long black hair and pale, gorgeous skin. She had flashing eyes and petite features. Her hair was up and I marveled at her long, slender neck.

"Do you have a table for us, honey?"

I composed myself and told her it was waiting for us. I signaled the waiter and he showed us to our booth, nicely out of the way and intimate.

"This is charming Dave, thank you."

After we ordered drinks, I put an envelope of cash on the seat next to her, as she had instructed me to. She put it in her purse without looking at it. She sat for a minute and engaged me in delightful conversation; light, fun with wonderful eye contact and sweet, unforced laughter. She was a gifted conversationalist and I immediately felt at ease.

After a few minutes, she told me she needed to powder her nose and excused herself. I suspected she was going to count the cash. After a few minutes, she came back to the booth, only this time sat next to me.

"Is that too close, darling?" she whispered, curling a finger in my hair. "If it's too much, I can sit opposite again, sugar." She was an extraordinary seductress, but never tawdry or cheap. I told her it would be nice if she sat by me. Her thighs brushed up against mine and she giggled.

"You're a sweet man, Dave."

She was great at making me feel as if she truly liked me and that I was handsome, in fact she made me believe it. I felt wonderful and the knot in my stomach loosened up. The waiter returned. He was young and good looking, but Sierra ordered her food without paying him any attention. Her focus was on me completely, her client.

After he was gone, she turned towards me and kissed me, softly and lovingly. She put her hand on my chest and then asked me if that was OK. I nodded. She kissed me again and her hand wondered down to find the lump in my pants. Her lips lingered close to mine and our hot breath mixed.

"Oh, David. You're a big boy." We both giggled. "I can't wait for you to take me" she whispered in my ear. I couldn't believe it. No girlfriend of mine had ever treated me like this way, in all my years. We kissed a little more and talked softly.

"You can touch me a little if you like, honey. Just be discreet please, lover."

My hands gently wandered over her body as she gazed in my eyes. I didn't want to grope her, but respectfully explored between her legs a little and caressed her breast. She closed her eyes and let out a soft moan as I did.

"Oh, Dave. I love your hands on me. This is going to be a wonderful night."

She made it sound so believable, I actually wondered if she wasn't acting. She was great at her job, but she made me believe that she was enjoying our time together. We had a wonderful meal, full of lively conversation, flirting, giggling and secretive touching and this was turning out to be the intimate experience I had hoped it would be.

As the meal went on, Sierra would feed me the odd mouthful of food and I did the same for her. During desert, I fed her a strawberry and she said "Dave baby, I need that to be your cock. Can we go soon?" I nodded and asked for the bill. I paid cash as I didn't need annoying questions from my wife, who was now completely out of my mind.

Sierra stood up, and she took my hand as I escorted her to my car. She allowed me to open the car door for her and I enjoyed treating her like a lady. When we sat down in the car, she leaned over and kissed me again, more passionately but just as tenderly as before. She let her tongue explore my lips in a way no woman had had done before and it was exhilarating

"Touch me," she said and I did, getting a real handful of her tits for the first time. She was perfectly petite. I looked at her as she smiled at me and I wondered how old she was. Early 20s, I guessed, and certainly about a third of my advancing age.

My heart was beating fast and I realized that this was a girl I could fall in love with, but who I would simply get to fuck a few times. I wasn't complaining, but did feel a stab of nostalgia for my romantic past. I drove her to my home and pulled straight in to the garage and closed the door before we got out. She didn't say anything, I knew she understood that I didn't need prying eyes on us.

We went inside and I opened a bottle of wine that I had bought specifically for the occasion, though I wouldn't be drinking much for obvious reasons. We continued talking, and she had a wonderful way of asking me questions without getting too personal or making me feel uncomfortable. I asked her a little about her background, but not enough to make me sound as if I was judging her profession. She asked if I minded her looking around my place a little, and watched her as she inspected my book and record collection.

"Good stuff, Dave. Do you want to put a record on? I love jazz." I agreed and went through the collection for the perfect item. "While you do that, why don't I change, honey?" I nodded excitedly and went back to picking out an LP that would enhance the mood.

She came back into the room in a little piece of lingerie that took my breath away. It was sexy but still stylish, revealing her tummy in the most gorgeous way. She was so beautiful and so sexy, I thought to myself that she was lovelier than any of the actual girlfriends from my past. When the music came on, she sat on the couch and patted the space next to her. I joined her and we made out with perfect body touches, caresses and explorations. As I nibbled on her earlobe and caressed her pert breasts, she would whisper little nothings for me to feast on.

"Would you like to go to bed now, baby, or stay here for a while?"

"We can stay here, Sierra, if that's OK."

"I wanted to hear this record anyways, honey. I'm sure you could teach me all kinds of things about music."

I felt a tinge of sadness then, knowing this would never happen, but I appreciated the respect she showed me. This sad thought was forgotten as she moved a leg across mine and then sat astride me as our kisses grew deeper and more passionate. She started rubbing her crotch against my large erection as I massaged her breasts and kissed her neck. I was in heaven. She started moaning, which only inspired me further.

"Baby, I can't wait forever for you to have me. When this record is over, can we go to bed, please?"

She grabbed my dick and of course I agreed. By now, she had me convinced that she really wanted to fuck me, and would have done it without being paid. As the music ended, and the needle sat in the run-out groove, I slapped her ass and she jumped off me, giggling. I took off the LP and she ran over to me and took my hand.

"Upstairs, honey?" she said with a twinkle in her eye.

"Lead on."

She jogged up the stairs, leading me by the hand. We entered the bedroom that my wife and I had shared for 25 years, and she pushed me down on the bed, sitting astride me. She unbuttoned my shirt and kissed my chest and stomach as she did. Then, she undid my belt, the button on my pants, unzipped my fly and pulled them down to the floor.

I had made sure I was clean and groomed for her, and I thought that I looked pretty good for a man my age. She looked up at me with my cock in her hand.

"Baby. Is it alright if I suck this? I mean, I'm not sure I can get this thing all the way down my throat, but..."

She didn't wait for me answer, and took me in her mouth. I could have come instantly. I didn't want to, though I remember reading that she allowed "msog" in her adverts which was a term I had to look up. It meant that I could come as many times as I liked during our session, which relieved some pressure. Sierra gave me incredible deep throat head, and mostly kept her eye on me as he did.

It was sensational to watch and even better to feel. My wife had always been pretty good at blowjobs, but this was better. I couldn't believe how beautiful this girl was, and that she was sucking my cock. I stroked her hair and fiddled with her ear, and floated away on a cloud. She stopped for a second.

"Baby, if you want to come now, you can. You can come in my mouth and then relax for a bit and then go again. Whatever you want to do is fine."

I didn't know how to respond. "Not yet, sweetie." I said and wagged my finger beckoning for her to approach me. She sat astride me again and wriggled around on my dick.

"Want to pull on my little bows, baby?" she said cutely. She leaned forward and I gently tugged at the bow at the back of her neck. She held her top up with her hands and then did a slow reveal of her titties for me. She looked perfect.

I cupped her breasts and then she leaned forward and fed them to me. She then sat up and asked me to pull the rest of her bows. I tugged on them and as they fell away so did her outfit. She pulled up her body so that her tenderest lady parts were in my face, and then slowly peeled her garment.

She wasn't wearing any panties and her perfectly groomed pussy was revealed to me. She had lovely little lips and a sweet line of pubic hair which I found highly erotic. My wife would never shave herself that way, even though I had timidly suggested it one night.

Sierra slowly and expertly removed her clothing and then pulled off my shirt so that we were both naked. Her flesh felt amazing next to mine. "Want a taste, baby?" she said and I could only nod. I had told myself I wouldn't indulge in any pussy eating with a hooker, but this girl was so young and clean, I couldn't resist.

She adjusted her body so that she was sitting on my chest, facing away, towards my toes. She then positioned herself over me so her pussy was close to my face. "Go on, baby," she said sweetly, and I lapped at her little pink flower.

Her reaction was immediate, and she writhed and moaned as I stimulated her clit with my tongue. Her juices started flowing and I thought to myself "you can't fake that."

She leaned forward and started toying with my swollen dick with her tongue. She sat down a little more on my face and made little squeaking noises as my tonguing grew more intense. Her sounds of pleasure increased, her body started shaking and as she appeared to reach an orgasmic climax, her thighs clamped around my head. It was a magical sensation.

"Baby, baby...I'm...uh...uh...gonna come," she said breathlessly. "Baby, you come too...come in my mouth...do it...do it."

She expertly brought me to orgasm as she wriggled her ass around on my face, moaning and groaning. I exploded in her mouth, and days of pent up spunk filled her sweet little mouth. I looked down and saw that I her eyes had gone wide. "Oh, yummy, Dave. Thank you baby," she said and hopped off my face. She continued kissing and licking my cock to make sure I was spent. She gave me a sweet little smile and then lay down beside me. "Baby, you made me feel great, " she said softly and of course I told her she did the same for me as well.

I looked over at the clock and saw that it was a little before 11pm. "Don't go to sleep, Dave. You still need to fuck me, OK?" she said, and fiddled with my limp dick. I thought I'd kill some time while I recharged with some more pussy and asked her if it was alright it I kissed her there again.

"Of course, baby. Oh, what a treat!" she said and spread her legs for me. I went down on her and started working my magic on her clit. I couldn't be sure that she had come just now and so I needed to make sure of it, as best I could. As I played with her young rosebud and fingered her, she started moaning loudly, saying my name, and "Yes! Yes!" over and over. She grabbed my hair and wrapped her legs around my neck as her orgasm hit. Her juices flowed and she was wild with ecstasy and I slowed down as she lay there panting.

"Dave, baby. I didn't fake it. You made me come. That was great. Thank you." I chose to believe her. "But now, I need you to fuck me. Are you ready?" I wasn't sure. She sat up and then started sucking me off again. All the desire came back as I went hard again. "Oh, yes, you're ready, lover. Hand me my purse."

I did as she asked and she produced a condom. She opened the packet and fed it over my shaft with her mouth. I couldn't help but smile at her professionalism. When she was done, she looked at me mischievously and asked "OK, how do you want me?"

We both laughed and I suggested we start missionary. She lay back, spread her legs deliciously and I just shook my head at her youthful perfection. I wanted to eat her out again, but didn't want her to get impatient with me, so I got down to business. I was nice and hard so positioned myself on top of her and slowly slipped inside. I liked to tease a girl, so gave her an inch at a time, pulling out a little, before giving her my full length.

She felt like heaven. She was much tighter than the pussy I had grown accustomed to over the years, and because I'd only ever received head from prostitutes during my married life, this was the first tight pussy I'd fucked in a long time.

"Oh baby, you're so big. Do it to me," she said and I went deep inside her. Iut didn't fuck her hard at first, preferring to savor the moment and not get carried away. We kissed and as our hands intertwined, this felt more like lovemaking that just sex.

"You're beautiful, Sierra," I couldn't help but tell her as we made love.

"Thank you, sugar. You're a very handsome man," she whispered back.

She smiled and her eyes sparkled as I tucked a strand of her hair behind her ear. I was feeling rather romantic, but the spell was broken when Sierra moved so that my dick pulled out of her.

"Fuck me from behind, babe," she said, positioned herself on all fours and I got up behind her. She looked so good and I stroked her breasts before entering her again. "Come on babe, I need it," she said, so I put my cock inside her without the customary teasing.

It felt even better than before. "Oh yeah, baby...uh...uh...yeah...fuck me...do it," she yelped as I gave it to her. I started fucking her harder than before and she continued encouraging me with dirty talk and beautiful little sounds. "Don't come yet honey. I want to ride you first," she ordered. She was truly great at her job. After a few minutes I pulled out and lay down.

"OK, sweetie, your turn to drive," I said and she jumped on me excitedly.

"This is my favorite part," she said and lowered herself on me. She started grinding on me and I touched her all over. "Oh yeah, that's deep, big boy," she said to me as she started riding me faster and harder. She sounded as if she was gonna come again. "Babe...you wanna come in me or pull out and come on my tits? Shooter's choice," she said breathlessly.

I laughed and marveled at the wonder of this girl. All I could say was "tits," as she slowed and sat still on me, slowly grinding her pussy on my cock. She just let out a long moan and then jumped off.