I went on to Front Page one Monday morning and there is a new red head called Jessica. Her body looks good, but it’s her hair that makes me curious. I want to know what she looks like. The ad says “light” eyes. Which is weird. They’re probably hazel.
I haven’t seen her ads before, so today must be her first day. I load her name into the whore phone. She has Natalie’s old number.
There were three very good-looking women on the train this morning. One was a tall blonde with dark eyebrows. She looked at me and I blushed because her pupils were dilated and her cheeks were flushed and she looked so hot. Then the people in between us moved and she was in a school uniform. She looked to be in her late twenties. I was shocked. The way she looked at me.
I moved and later our eyes met again and she had that same intense direct gaze. Fuck!
There was a woman in tight slacks who looked like Natalie. She had a great figure and a hot little ass that was strangled by the pants.
Then there was a very cute Thai girl in a leather jacket with her hair dyed platinum. She was gorgeous.
I wasn’t really in the mood for anything this morning, but the women on the train changed that. I would like to book Jessica. Be her first customer. Eat her out and make her come. And then spurt all over her face. That would be so cool to induct her into the 140 Club like that.
It’s unlikely, but I’m going to give it a shot.
Unfortunately there is a crisis at work first up and I don’t get to text her until nearly 11 am. I had planned to book her for 11 to ensure I was the first.
I text her and we’re on for half an hour at noon at Katherine Place. I take half a Viagra and hydrate. I am delayed leaving the office.
On the way here, I try to get in the zone. If she is shy and lacking in confidence, she may not want to be eaten straight up. She might have her period. She might let me do it, but be too self-conscious to let herself go and come. I wonder what she looks like. If she is not pretty, I won’t want to waste $100 on her face. I only enjoy it when they are pretty to look at.
I rush and get there just in time at 11.59. I text her. This is not going to plan.
She buzzes me up to room 1507. Same as Alice on Friday. I catch my reflection in the mirror in the lift. “What are you doing?” I ask myself, out loud. This seems like such a folly.
When she opens the door she is good looking and tall and has the lovely long wavy red hair promised by the photos. She smiles. She has a gap between her two front teeth. She’s gorgeous.
“Hi. I’m Andy.”
“Come in, Andy.” She waves me in. She is wearing a silk happy coat. She beams and looks happy and excited.
She leads me through the living room to the back bedroom. There is a phone girl talking to an escort. Looks like the short Italian escort from last time. I check out Jessica’s legs as I follow her. Her skin is milky white and her legs are long and athletic. They are those strong Scottish legs. Shapely and lovely. Like Kitty, but longer. She is probably five ten. Her hair is lovely.
I give her $140 and she leaves me.
“I’ll give you 5 minutes to get ready.” That seems a bit long. I start to strip and use an antiseptic wipe to freshen up my bum. She comes back before I’m fully undressed. She knocks and comes in.
“That was quick. I’m not quite ready, but come in anyway.” I take of my shirt and I’m naked. She takes off her gown and climbs on the bed, on the towel. I climb on. She’s on the towel where I should be.
“Do you want to start with a massage or . . .?“ I’m a bit taken aback. She’s very pro-active for a girl on her first day. Maybe it’s not her first day. We only have half an hour and I’ve got a lot to do, so skipping the massage sounds like a good idea.
“We can skip the massage and get straight into it, if that’s OK with you.” I lie down on my back. She is sitting up on her knees, grinning and sweeping her mane of red hair back off her face.
“Sure.” She climbs on top of me with her crotch spread wide over mine. She has lovely long white thighs that straddle me easily. She puts her hands on either side of me. Her face is above mine and her hair trails down around me.
“I love your hair.”
“Thanks.” She beams.
“There aren’t many redheads around. I assume it’s your natural colour.” I caress her thighs and her waist. She has a trim waste and broad hips. Her proportions are lovely. She wears a bustier style bra that seems to cover small boobs. She is wearing panties that are high waisted like something from the 90’s. It is a sheer Lycra thong in midnight blue. She presses her crotch down hard against the chubby and starts grinding. She looks at me and smiles a sexy smile.
“Yeah, it’s natural.” She is staring into my eyes in a very direct way and smiling and giggling, like she can’t believe her luck. Like she’s having more fun than she expected.
“You’re gorgeous, Jessica.” She giggles again. She’s got a cute giggle.
“Thank you. So, what do you want to do?” She is very assertive. I love it.
“Do you kiss?”
“Sure.” Without further ado, she leans down and plants her lovely soft plump lips on mine. It is a lovely kiss. Her lips are so soft and ripe. There is a funny taste of her mouth. Like she has been eating pussy. I like it.
Her hair falls around my face and she sweeps it out of the way. She has a silver necklace with some dark blue gemstone in it and it dangles near my chin as we kiss.
She breaks away and sweeps her hair to her left and lets it hang down to the right of my face. I caress her waist and clutch her ass as she grinds her pussy on my erection. I groan and she giggles. She’s pleased with the reaction she’s getting.
“Sorry, my hands are cold.”
“So are mine,” she says.
“Never mind. We’ll warm up soon enough.” She giggles and attacks me again with her mouth and I grope her warm body with my cold hands. After a minute, she breaks free again. “I haven’t seen you before. Are you new?”
“Yeah, I’m new.” She keeps grinding on my erection and kissing me while I hold on to her gorgeous figure and groan.
“Wow. In at the deep end.” She giggles and kisses me.
“Yeah.” She stares into my eyes as she grinds hard on my cock. I gasp and she tosses her head back and giggles again. She seems amused by how easy it is for her to push my buttons.
“I’m impressed. You’re a lot of fun Jessica.” She smiles and we kiss hungrily. I feel like we’re on a runaway train. I grope her tits through the bra.
“Do you take this off?” She sits up and reaches behind with both hands.
“Yeah. You wanna see ‘em?”
“Yes please.” She unhooks the bustier at the back and throws it away. Her soft pale tits are marked with creases and red lines where the wire frames of the bustier have bitten into her soft skin. Her boobs are small, with small areola and soft pale nipples. I reach up and cup them. They have a surprising heaviness and warmth.
She leans down and kisses me and I put my arms around her bare back and shoulders and hug her. She kisses my neck and I kiss hers. She giggles with pleasure. I hug her close to me and kiss her tender skin. She is so soft and warm and gorgeous. She pulls away slightly and her boobs dangle near my face.
I kiss her right nipple and then suck it gently. There is nothing there to begin with. It is just soft stretchy skin. But as I suck and nibble, it fills and hardens. She gasps and I can tell she likes it. I’m surprised. Nipples that small and soft usually stay small and soft. But hers are suddenly rock hard. It’s an extraordinary transformation. I expect her to tell me to stop. Tell me that they are too sensitive. But I bite harder and she just gasps and groans and grinds her clit harder into my erection.
I reach down over her big, firm arse and trace over the thong that cleaves her cheeks. I rub over the smooth fabric that barely covers her anus as I suck hard on her nipple.
“Ah!” she gasps. For a fleeting moment it sounds like she is going to tell me off, but it is only a noise of surprise and she keeps grinding into me and gyrating her hips as I rub firmly back and forth over her anus.
I swap nipples and the left one is still as soft as the right one was to begin with. But it swells and hardens quickly in my lips and teeth and the right one stays hard as I pinch it with my left hand. My right-hand slides under the fabric of her thong to explore her hot anus and wet pussy underneath. She winces and gasps.
She hoists herself up on her long arms, pulling her nipple from my mouth and towering over me. She is an impressively tall woman in a dominant position. She grinds on my erection and stares into my eyes lustfully.
“Do you take these off too?” I ask, flicking the elastic of her panties against her skin. “Or is that too dangerous?”
“I can take them off,” she says. “You’re payin’. You decide.” But without waiting for me to decide, she tumbles off me and pulls them off with her knees bent up to her chest and her feet in the air. I get up on my knees. She is lying diagonally across the bed with her beautiful hair spread out on the pillow. I climb between her legs. I reach down and touch her pussy with my fingers. Her lips are a sloppy mess. She was worked herself into a lather with all that grinding.
“Oh my god, Jessica!” She grins sheepishly and puts her finger to her mouth and turns her head into the pillow with embarrassment.
“Can I eat your pussy?”
“Yessss . . .”
I drop down into position. She is so pale. Her skin is clear. No tattoos and no freckles. Her pussy lips are neat and raw pink. Her bush is shaved, except for a cute little triangle of red pubic hair.
“What a cute little red bush!” I run my fingers through it. I’ve never seen the genuine article before.
I start licking her and she lies back and enjoys it. She is from the quiet school and she gyrates her crotch gently in my face as I lick. She looks down at me a couple of times, but mostly keeps her eyes closed and her face looks up at the ceiling. I love holding her soft skin in my hands. Her soft hips. Her soft waist. I reach up and grope her soft boobs.
She writhes and tenses and we seem to get very close very quickly and she gasps and her pelvis shudders. It could be an orgasm, but it seems to pass too quickly and she relaxes and breaths out and lets me keep going and I assume we didn’t quite get there.
I dip my tongue down into her hole and taste her puffy wetness. She has no taste, but she feels wonderful.
The cycle repeats every 4 or 5 minutes for the next 15 minutes. If those were orgasms, she had 3. But I’m not sure and I’m still pressing for the bucking and screaming variety. But it never gets to that and I run out of stamina. My neck is sore and my tongue is tired.
“I’ve run out of steam.”
“I think we both have,” she sighs. I climb up on top of her, with my knees still between her legs. I lean in and kiss her with her own juices all over my face.
“Did you like that?”
“I loved that,” she sighs. She seems more content than I expected. I sort of thought I’d left her hanging.
“Did you come?”
“I did. I did,” she kisses me dreamily. “I did.”
I have her in the Alice position and my erection is pressing into her pussy lips. I prod her gently while I kiss her, testing for her reaction. She keeps her legs splayed and lets me have my way with her. She doesn’t want to move or stop me. She seems even more game than Alice.
I keep probing and kissing and she doesn’t object and I begin to wonder if she is up for it. My cock is not fully erect and I couldn’t slide it in, even if she would let me.
I kneel up and put the tip of my cock to her clit and rub it around. She just lies there, watching.
“So tempting,” I say. She giggles. “So tempting.” She lets me play and my cock is leaking and I pull back and rub the pre-cum all over the head and I throb harder. I reach down with my left hand and run my thumb through her swollen pussy lips and she is soaking wet.
“Oh, Jessica!” She giggles. She is still lying there, her legs splayed and her pussy open for me. Her hair is spread out on the pillow and her eyes are lazy with lust as she stares at my cock hanging over her mound.
“Let me just feel some of that wetness.” I am pushing my luck. Pushing her boundaries. I hold the head of my cock against her clit and rub it down through her lips into the wetness above her hole. She lets me do it. I can’t believe it. I rub the head of my cock up and down through the swollen lips above her hole. Up and down. Up and down. She is so wet and it feels so good on my cock and she just lies there and watches me, with her breath catching.
I can’t believe it. I can’t believe it. She is going to let me fuck her.
I put my cock all the way down to her hole. I press gently against her entrance and then I draw it back up to her clit. Then back down and engage with her entrance and press lightly. Will she let me go in? It feels so wet and wonderful.
But she puts her hand to my pubic bone to hold me back and she presses her ass down into the mattress so that my cock is back up near her clit.
I get the message and pull away and rub her wetness all over my head with my right hand and I rub her wet pussy with my left thumb. I dip down. She is so gorgeously wet. So soft and swollen. I want to finger her.
“Can I put my finger inside?”
“Not today,” she says. She smiles and writhes as I keep rubbing her with my thumb.
We keep playing with fire. I keep rubbing her with my thumb, keeping her clit hard and her juices flowing. And then I bury the tip of my cock in her wet lips, rubbing it up and down and spreading her wetness. Holding it at her entrance – engaged, but never penetrating her with that pop that would be so wonderful. We keep going for the next 5 minutes.
She is relaxed and horny and she wants me there and she’s happy to let me do it as long as I don’t penetrate her. My heart pounds and I am entranced. I can’t believe she is letting me do this.
“Do you do extras?”
“No,” she says uncertainly. She thinks I mean “full service”. “Not really. What kind of extras?”
“Can I come on your face?”
“Yeah. You can come on my face.”
“For a hundred?” She nods.
I start wanking my cock while I rub my thumb through her swollen wetness. The feel of her is such a turn on. She is still very wet.
It is so hot to watch her from this position. She is still splayed and open and a flushed heat seems to rise from her pussy and her face. My cock gets harder and my orgasm gets closer. She stares at my cock and compresses herself slightly, as if she expects me to hit her in the face from down here. That’s not likely today.
“Can we get on the floor?” I ask. I am so close.
She climbs across the bed to kneel near the door. I stand with my back to the door.
She looks beautiful and she spreads her feet out from under her ass and has her ass flat on the carpet, like Rachael. Her lovely face is under my cock and she smiles serenely. The sunlight is coming through the blinds and it lights up her hair and my orgasm rolls into place.
The first squirt is not a big one. The spider web never breaks free of my cock and the thread stops and swings down onto her lips like some failed trapeze swing. The next one fires further and lands on her forehead. Then one drops on her nose. The next squirt hits her in the right eye, which is closed. She flinches, but assumes it’s over and relaxes and then another one hits her below the right eye and the tail drapes over her cheek. Another one squirts on her nose and then the last few dribble on her lips and her tits and her lap. It didn’t fly very far, but there was a lot. None of it went in her lovely hair, but I painted her pretty face really well with that nine squirt load.
She sat there with her face screwed up and my cum oozing down her face for a few moments – not really sure if the unending orgasm was finished or not.
“Thanks Jessica. That was great.” I was too busy recovering from the orgasm and admiring my handywork to offer her a tissue. I grabbed the towel to wipe myself down and she must have spotted that out of her good eye because she grabbed the towel and started wiping her face. She wiped and she wiped and she wiped.
“Gee, that was a lot more than I expected.” I sat down on the bed beside her, while she stayed on the floor, now dabbing the cum off her tits and her thighs.
“That was your fault,” I laughed. I was panting to get my breath back and my body was still trembling from the orgasm. “That was more than I expected. Thanks, Jessica. That was sensational.” I stroked her upper arm affectionately.
“You’re welcome.” She was giggling again and I was chuckling. I still can’t believe she did that. Letting me rub my cock over her pussy. On her first day. I leaned over and gave her a kiss on the lips.
“Thank you. That was amazing.” I flopped back on the bed, chuckling in disbelief and panting with exhaustion. “You’re off to a flying start. I’ve never had an experience like that on a first date. I reach out and stroke her hair and her back as she stands up. She giggles at my reference to a first date.
I stand up and go to the corner to get dressed. I get her the extra money and she is surprised and delighted.
She decides to make chit chat as we get dressed. It’s funny to do that so late in the piece. She asks me what I do and if I’ve had a busy morning.
“No, not that busy. What about you? This is your first day, but I assume I’m not your first customer.”
“No. Number two.” She is packing up and grabs her phone.
“The alarm hasn’t even gone off,” I observe. “We packed a lot into less than 30 minutes. That was so intense.”
“Do you come here regularly?”
“Yeah. Every week or two. Why? Did they tell you about me?”
“No. I just wondered.”
“I was here last Friday with Alice. I think she’s here again today. Is she?”
“I don’t know. I don’t know everybody’s names yet.”
We finish getting dressed and she leads me out. The escort is still there with the phone girl.
I give Jessica a kiss on the lips and thank her.
“Lovely to meet you, Jessica . . .”
“Yes, likewise. See you next week.” She beams.
“See you next time.”
There are people in the hall waiting for the lift.
I am muttering to myself and groaning under my breath all the way back.
Fuck that was good. That was so good.
