He’d walked me home at the end of the date and we’d kissed on my doorstep. Every fibre of my being had longed to take it further but I hadn’t wanted to seem easy, so I’d gently pushed him away. I’d expected him to attempt a second kiss, or ask for a second date, but instead he’d looked hurt and rejected and hurried off. I hadn’t had any contact details and had never seen him in the intervening five years. But now I had a second chance . . .
I walked over, hips swaying in what I hoped wasn’t a hurt-myself-at-the-gym kind of a way, and gave him my best smile.
“Hi, Jason.”
“Sarah!”
That was a good sign: at least he remembered me.
“So you’re the guy I come to when I fall off my high heels?”
He grinned back. “Only if you trip over a loose paving stone.” Then his smile faltered. “Can’t believe my business degree only led to this.”
“Hey, mine only got me a job in the bank. Blame the recession.”
I wondered if he’d thought about male modelling or making porn.
“Oh, I had a better job but I lost it after my marriage failed because I was so depressed.”
“You married after college?”
“Uh-huh, but it only lasted three years.”
Let me console you against my ample bosom, I was about to say when one of the aforementioned white-collar psychopaths approached.
“Mate,” he said, “the hot water in the Gents scalded me hands.”
Jason got out his notepad and I reluctantly exited stage left and went to work.
As luck would have it, I saw him the following Tuesday, lurking in the city square. It was market day so everyone was rushing past him with bulging carrier bags.
“I’m popping into Debenhams for a coffee,” I said casually. “Fancy one?”
He did and we had a lively half hour. We had a similar sexless session the next time that we met and all I got out of it was way too much caffeine. I hinted broadly that I’d love to go clubbing or meet up for an evening drink but he didn’t take the bait.
Then, one day we were chatting outside the museum when Lucy, who I’d known at college, walked over.
“Meet my former better half,” Jason said.
Lucky bitch, I thought but merely asked, “You two were married?”
“And still friends!” Lucy kissed him on the cheek then turned to me. “Sarah, let’s have a girly night out.”
We sank a few black ’n’ tans the next evening and she told me that, despite his looks, Jason wasn’t the most confident of men.
“It’s not true that good-looking guys get lots of sex. In fact, women assume that they’ll be one of a long line of casual lovers so tend to give them the brush-off.”
“So, when I played hard to get he thought I didn’t like him,” I said slowly. “And he doesn’t want to get rejected again.”
“He’s throwing himself into other things now,” Lucy added. “Everything from the gym to this injury lawyers lark; all that he can get in the current market. He mainly works on commission so really puts in the hours.”
On the way home, I saw several road workers doing a late shift, drilling into the floodlit concrete. And suddenly I knew how I could seduce Jason and give him the best sexual experience of his life.
The next day I wandered around his usual sites and found him outside the library. I’d dressed with care, didn’t look at all bookish.
“I want to pursue a claim for compensation,” I said.
He got out his notebook with a flourish. “Then I’m your man.”
I smiled shyly and tried to look as innocent as a baby rabbit. “The problem has been a lack of men and I’ve been using a vibrator most nights. I think I’ve got Vibration White Finger, you know, the condition which mostly affects road drillers,” I said.
Jason’s eyes opened wide and I swear that his pupils dilated. For a moment he seemed lost for words and then he donned a professional air. “Tell me more, madam. Perhaps I should get my pencil out?”
“I think that’s essential, sir. Come home with me now and see the evidence for yourself.”
Back at my terraced house, I led him upstairs, sat on the bed next to him and reached into the adjacent cabinet, bringing out my favourite oscillating dildo. Like most women I mainly use my vibrator by resting it on my pubis, near my clit, but I knew that Jason would get more turned on if he saw me sliding it inside. I’d have to get really, really wet first, of course.
“Feel how powerful it is,” I murmured, switching it on and pressing it into his hand. “Can you imagine how strongly these vibrations have throbbed through my fingers and pussy lips?”
Jason cleared his throat. “For your claim to be validated you’ll have to demonstrate,” he said.
“Certainly, sir.”
I undid my skirt and slid it off, revealing light-grey holdups. They’re uncomfortable as hell but I’d put them on a couple of hours ago knowing that, if Jason wanted me half as much as I wanted him, I wouldn’t be wearing them for long. Black was a bit too obviously vamp-like, hence the grey.
I took off my panties – no, not grey, a newly bought white – and lay back on the duvet, spreading my legs wide apart. I looked up at Jason and he was staring intently at my lightly trimmed pubes.
“Where exactly do you hold the dildo?” he asked, obviously striving for professionalism.
“Here to start off with.” I ran the vibrating sex toy over my mound and began to feel really horny. “But you can feel how strongly it vibrates through my palm.”
I took his hand and placed it over the plastic shaft and he shifted so that he was lying on his side facing me, one of his legs over mine.
“I can certainly see that Vibration White Finger or even Vibration White Vagina could occur in these circumstances, madam,” he said. He started to move the dildo over my pussy and I began to make the odd little noises that I always make when I play with myself. It was great to have someone else doing it for me as it had been a while. Most of the other women I worked with at the bank were married so there weren’t many nights out, few opportunities to bag a bloke. I’d had a brief trial of match.com but no one had had Jason’s looks or personality.
“This machine is so strong that it may even be making your nipples vibrate,” he continued. “I have to make a full inventory of the situation so can you take off your blouse and bra?”
I couldn’t quite meet his gaze as I undid the buttons, removed the silky garment and unclasped the bra (new, white, with a lace trim) which held my 34Ds in place. Now I was naked except for my hold-ups yet Jason was still dressed in his business suit. It made me feel really vulnerable yet horny at the same time.
“Hold this close to your clit while I examine your breasts,” he ordered, taking my fingers and bending them around the dildo.
“I shall do my best to comply with your instructions, sir,” I replied breathlessly.
By now I could tell that I was lubricating nicely, a situation which intensified when Jason began to caress my best feature. I was slightly premenstrual so they were at their fullest and perkiest.
He stared down at me. “I should really nibble on them for a while to make sure that they aren’t too tender, madam.”
“I should think it’s vital for your report,” I said.
I felt his warm tongue on my left nipple, his lips gently encompassing the hardening bud. He repeated the gesture with my right while I kept one hand on the vibrating sex toy and the other on his head.
“I should really conduct an internal probe,” he said throatily when he finally lifted his head from my appreciative bosom.
“I’m glad that you’re prepared to be so thorough,” I replied. By now I was desperate to see him naked so added, “But it would be dreadful if the injury lawyers’ rep got overheated while conducting an investigation. You’ll have to take off all your clothes.”
“You’re right, of course.” He removed his jacket and tie and I began to unbutton his shirt. He had a wonderfully hi
rsute chest and I stroked it eagerly. I’ve always loved lots of body hair, appreciate the caveman look.
Soon he was down to his socks (midnight blue) and almost-matching boxer shorts. He stripped off his socks himself and I chivalrously helped with his underwear. Well, a several-thousand-pound claim might depend on his not being overheated – yeah, right – so I was ostensibly in business mode. I naturally wanted him to feel that he’d put in a good morning’s work as Lucy had said that he was giving his all to this job until something more suitable came along.
When he’d finished undressing he lay on top of me and I could feel his manhood pressing into my stomach. I smiled to myself: it was of no use to me there. I couldn’t wait to feel him inside me, especially love the moment of penetration where I feel myself being opened up.
I took hold of his cock. It wasn’t particularly long but was beautifully thick, just the way I like it. It wouldn’t bang uncomfortably against my cervix but would fill me right up.
“Sir, if you’re ready to check inside?”
“It’s my sworn duty.”
I parted my thighs and took hold of his shaft, positioning it at the entrance. I was wet, wet, wet so he slid in easily. I cried out at the sweetness of the sensation and he smiled knowingly down at me.
“I’ll check all the way up by thrusting like this.” He pushed in and out forcefully for a moment. “Then check the outer walls by circling my cock again and again.”
“I can feel the sensitivity previously caused by the vibrations,” I murmured. “If you keep going it’ll help me to give you a fuller report.”
“Shall I keep going until you reach orgasm, madam?”
“Oh, yes! I appreciate your dedication to your work, sir,” I gasped.
I lifted my lips to his and he kissed me with increasing fervour, gently exploring my mouth with his tongue. He kept thrusting, a beautiful rhythm that I could rely on. I cupped his hard oval buttocks and pulled him even further in. This wouldn’t take long as I was already halfway there from using the vibrator. But he felt – and looked – so much nicer than any sex toy ever could.
In, out, in, out. I ran my fingers down the crack in his arse and heard his breathing quicken. In, out, in, out. I kissed his neck and was gratified when he nuzzled into mine. He thrust on and on and on and I felt the almost signal. Seconds later I climaxed strongly, half aware of my guttural cries echoing around the room. We have small rooms in Salisbury – often on several levels as there’s little space to build outwards in such a small city – and my groans seemed to echo eerily around.
Obviously undaunted by the sound show, Jason kept thrusting. By now I felt almost too sensitive to be touched down there.
“Too much,” I whispered and he must have stopped thinking about the football results, or whatever he was concentrating on to delay his orgasm, let himself appreciate the full arousal of the moment, and promptly came. He was quieter than me (most men are) but managed an appreciative grunt as he strained forward, his face hidden in the pillow as I stroked his hair.
We lay there for a few minutes, utterly content, then I felt his shaft shrinking inside me, felt the deluge trickling out. I hate that bit. It means changing the undersheet (black Egyptian cotton) and having to make toast and tea.
We chatted, sometimes half-dozing, for a while then I looked more searchingly into his dark eyes and felt my excitement start to build again. He was the most perfect specimen of manhood that I had ever had in my bed. It was a cold winter’s day so I was pale and hopefully interesting but he had the kind of olive skin that always looks tanned.
“So, am I entitled to injury compensation?” I asked softly, running my right palm down his endearingly flat stomach.
I felt his penis twitch and begin to lengthen.
“I’m just wondering if the vibrations could have worked their way back to the anus,” he answered. “If so, it would double the likelihood of a successful claim.”
I felt a stirring of doubt. “Jase – no! I don’t do anal.”
“Me neither, madam. I’m simply suggesting that we switch on the sex toy in the vicinity of your bottom, see how it feels.”
“You really think that’s necessary?”
I’d had one boyfriend who wanted to try it up the chocolate freeway and, suffice to say, after he’d got it in an inch I’d had enough of biting the pillow. I’d pushed him off so violently that he almost landed on the floor. Now I was worried that the beautiful Jason was going to push his luck – and his admittedly compelling manhood – and try to penetrate me there.
“A professional investigator explores every avenue,” Jason said.
Alive with nervous anticipation, I rolled onto my tummy, felt the vibrating toy being played over my vulnerable buttocks. Within moments he was concentrating the oscillations on my anus, the waves of pleasure rushing through me all the way to my clit. I’d never used the vibrator on that area, or even while lying on my stomach, was amazed at just how good it felt.
“Again, I have to check all the way inside,” my new lover murmured. I tensed, fearing that he was about to push the sex toy where the sun doesn’t shine then relaxed when I felt his cock nudging at my vagina. Aha, so he was going to take me from behind.
I carefully got onto my hands and knees, knowing that doggy style always allows for the deepest penetration, then reached back and guided him into my wetness. He must have switched off the vibrator as I could no longer hear its telltale buzz. Not that I needed it anymore: being shafted by Jason provided more than enough stimulation, especially as he was able to reach forward and play with my breasts.
The second orgasm – for a woman – is always more intense than the first, so I made enough noise to bring down the rafters.
“God, I love that sound,” Jason whispered and climaxed, grinding his stomach against my upturned arse.
It was well after lunchtime when we took a lingering shower together.
That was three months ago and he’s still investigating my condition as he apparently has to check out my vagina in different kinds of weather and at various times of the day. He also has to make sure that my fingers are working when I’m doing everything from watching television to peeling potatoes at the kitchen sink. He’s had me over the aforementioned sink, on the table and under a large tree in the forest. He even sneaked me into his work after hours and we did it in the lift.
He had an interview as a team leader with a software firm the other day and it looks likely that he’ll be successful so I doubt if I’ll ever get to put in a formal claim with the injury lawyers though I’ll bet it would send a few of them rushing to the Gents to enjoy a swift hand shandy. God knows, it would be a lot more interesting than people claiming that they’d slipped, with cartoon-like drama, on a wet supermarket floor.
A guy like Jason tires of missionary pretty quickly so I’ll keep him enthralled by ordering new sex toys from the internet, pleasuring him with everything from a vibrating sheath for men to a non-doctor that I can tease around the entrance to his arse. We also have lots of role play to look forward to and I will enjoy being everything from an adult schoolgirl to a naughty nurse.
Schoolgirl Dreams
Cotton, Chicago
Rick and I had talked about it for weeks, and we finally decided that we wanted to give it a try on Friday night, when the kids were at my mom’s for the evening. That was why I was standing outside of our bedroom dressed in a short plaid skirt, a white button-down and nothing else.
We’ve definitely role-played before. This wasn’t even the first time I had worn the plaid skirt, but it was nothing like this. This was a lot rougher and a lot darker than anything we had ever done before, and Rick asked lots of questions before he would even venture a “maybe”.
“I’m not going to call you Daddy,” I said, shaking my head. “Not . . . this time, anyway.”
“OK, then who am I?” he asked practically. “Am I a babysitter? Am I your big brother?”
The moment he said “big brother” the t
erm leaped out at me. I was an only child, and the idea was intriguing to me. We roughed out what we wanted to happen, left some room for surprises. Now it was Friday night, and it looked like I was all alone in the house.
I stepped into our bedroom, closing the door behind me. Some of my old stuffed animals were tossed on the bed, and they helped set the scene a little.
Sighing, I pulled my hair out of my ponytail and let it swing free before unbuttoning my skirt. No lacy numbers tonight, just plain white cotton.
I stretched dramatically before flopping down on the bed. I remembered doing just this when I was a teenager, feeling that delicious lazy, almost sleepy feeling drifting over me. Without thinking about anything in particular, I rolled on my back and slid my skirt up my thighs. I pushed the cotton underwear out of the way and ran a finger up my slit gently. I had shaved first thing that morning, and I was silky smooth. There was nothing between my fingers and how slick I was getting. To be perfectly honest, I’d been damp for a while, thinking about this.
I could have drifted off, fingering my fresh, clean pussy, but then the door opened, and Rick stepped in.
“What the hell do you think you’re doing, Cotton?” he asked, but the grin on his face told me that he knew exactly what he was looking at.
I shoved my skirt down over my sopping pussy, but there was nothing I could do about the wet on my hand.
“Rick!” I wailed, my voice far higher than it usually was. “Get out! Get out right now!”
Instead of doing what I told him, he crawled on the bed with me and snatched up my wet hand before I could pull it away. He’s not heavy, but he’s built big, and his hand clamped around my narrow wrist tightly.
“Be quiet, Cotton, or I’m going to tell Mom and Dad what you were doing. You think they’ll like to hear that; that perfect Princess Cotton was diddling herself like a girl at a peep show?”
My face burned red with humiliation, and I could feel myself get wetter just from hearing him talk.
The Mammoth Book of Urban Erotic Confessions Page 51
