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Nicki and Jen

Nicki's first time
This story takes place straight after "My Boy Nigel"

The next day was warm, so I put on a dress and a pair of strappy Roman sandals, and took a stroll down into town. An hour of window-shopping left me hot and thirsty, so I walked down to the seafront and found myself an ice cream. I sat on a bench and looked out across the beach and the sea. A few minutes later, as I was catching a dribble of melted ice cream with my tongue, a woman sat down on the bench: “There’s no one sitting here is there?”

“Not at all. I’m by myself today.”

“Lovely,” she continued, “I could do with a sit down.”

I glanced over at her; she was twenty years my senior, I reckoned, but in really great shape. She was wearing a black pencil skirt and a white sleeveless roll-neck top that showed off her shape to good effect. I couldn’t see her eyes behind her big tortoiseshell sunglasses.

“It is very hot, isn’t it?” I offered.

“Certainly is.” she replied. “I've been shopping all morning.” There was a pause. “Retail therapy.”


“Retail therapy.” she smiled. “You know—cheaper than therapy. Especially when I use my husband’s credit card.”

“Oh.” The penny dropped. “Sorry—just not heard the term before.”

“Well, I have been doing it for years—only just learned the word for it recently. And when I need the therapy because of my husband, it is ironic that I spend his money to make myself feel better.”

I gave a chuckle. “I hope he hasn’t done anything too horrendous.”

“Well… Not really I suppose. He just came home late last night, and went straight to bed. I normally get some on a Friday, but the poor lamb was too tired.”

“Oh I see.” I replied. “So feeling a little… frustrated?”

“No shit! Haven’t had any cock in over a week.”

I gave a little guffaw; a little shocked at this revelation.

She chucked at my reaction. “Mmm. I’ve always been a straight talker. Got me into trouble often enough. Don’t take offense.”

I recovered my composure. “No problem. Just slightly… unexpected.”

“Oh good.” She leant over and offered me her hand, “By the way, I’m Jennifer. Call me Jen.”

I shook her hand, “Nice to meet you, and I’m Nicki.”

“Nicki.” She repeated, with a nod.

I had been neglecting my ice cream and felt a trickle of vanilla on my fingers. I caught it with my tongue and licked around the base of the cone to try to get ahead of the game.

“An expert, I see.” Said Jennifer.

I smiled and took another lick. “Just trying to stay on top of it before the whole thing melts.” I liked Jen. She was straight-forward and relaxed; she had a good sense of herself. Someone I immediately felt comfortable with; I was sure she made friends easily.

“It does look good.”

“Tastes good too.” I held it out, “Want a lick?”

Jen took the cone from me, opened her mouth and put what remained of the ice cream in her mouth, sucking it in. When the cone came out, there was still a bit of ice cream, but only a bit. She handed it back. “Oops. I took a little more than I thought. Sorry.” She licked her lips, “It was good—thank you.”

“You’re welcome.” I loved the sensual way she had slowly licked her lips. Something in the pit of my stomach was all a flutter. But, I had changed over the past couple of months. Before Nigel, before Auntie Mary, or my other adventures I would probably have run a mile. Now, I could take that feeling in my stride; I could wonder what might come of it, what might come of this conversation. I could think about what I wanted, and where I wanted this conversation to go.

“So,” I said, “What are you going to do?”

“Do about what?” asked Jen.


It was her turn to start in surprise, my turn to smile.

“Oh. Oh that. I don’t know. It isn’t that long ‘til next Friday.”

“It’s another week…” I pointed out.


“And who is to say what your husband will do next Friday.”

She rolled her eyes. “Too true.” she looked at me and frowned a little. “Are you suggesting something?”

I grinned. “I don’t really know. Just… maybe that you don’t want to rely completely on your husband.”

Jen started, then leant closer to me, “You’re… you’re not a tranny are you?”

It was my turn to laugh, “No, no. I am 100% woman. No one’s ever asked me that before, either.”

“Sorry. No offense meant.”

“None taken.” I paused. “But I do wonder whether you need a man to be satisfied.”

“You’re a lesbian?”

“Heh. No. In fact I’ve never been with a woman. But I wouldn’t be averse to trying.”

“Wow.” Said Jen, “If I didn’t know any better, I’d think you just propositioned me.”

I smiled broadly at her, “I did.” There was silence between us. The world rushed around us: waves crashing on the beach; families ushering their children passed; dogs taking their people out for walks along the promenade, and silence hanging in the air between us.

I popped the last of my ice cream cone into my mouth, and finished it off. I stood up, swallowed and said just one word: “Come.”

Jen stood up and followed me; then, walking side by side, we went back up through town and to my flat. The silence between us an oasis of calm as the sunny afternoon bustle continued all around. I opened the door to my flat and let Jen in before me; she walked through to the living room, put down her shopping bags and handbag. She turned to face me. “This is nice.” she said, as she took off her sunglasses.

I stood close, seeing her eyes for the first time: a penetrating grey. I put my finger to my lips, then leaned forwards and kissed her. The first time I had ever kissed another woman; so soft, so sweet. I put my hands on her hips and kissed her again, my tongue flicking at her lips until her mouth opened. My tongue found hers and our mouths opened, kissing properly now. My hands moved to the small of her back and I pulled her towards me, feeling the swell of her breasts against mine. One hand on her back, the other cradling the back of her head, holding her mouth against mine, her hair entwined in my fingers, my tongue feasting on her mouth.

Finally, I released her, let her catch her breath, “Oh… my God.” She whispered.

I smiled. “I don’t think you’re going to need to wait ‘til next Friday, are you?”

“Oh fuck, I hope not.”

I took Jen’s hand and led her into the bedroom. I pointed at the bed and whispered, “Sit.” She sat on the bed and I smiled as I looked down at her. “I’d like to make you cum.” I whispered. “Would you like that?”

Jen just nodded in reply. I knelt down in front of her, my hands on her thighs, and smiled as I looked up into her face. I raked my fingernails slowly down her thighs, as she closed her eyes. The tips of my fingers slid up under her pencil skirt, and she groaned. I let my fingertips explore her legs, through her stockings. Sliding up and down, feeling her firm thighs under her skirt, watching her head fall back, open mouthed, eyes shut and moaning.

My fingertips found the top of her stockings and edged them down just a bit. Then I found the hem of her skirt and pushed it up. Hands on her knees, I edged her legs apart, which pushed her skirt further up her legs. Then I could see the gusset of her lacy black knickers. Fingers raked down her inner thighs, and pulling down her stockings, making her gasp. I leaned down and kissed her legs; one, then the other—just little pecks. I kissed her over and over again, slowly working my way up her legs, passt her stocking tops and onto bare skin.

The tip of my tongue traced tiny circles on her skin, and I could hear Jen moan. As my tongue slid down between her thighs, I knew she must be able to feel my hot breath on her pussy; my hands reached up and cupped her breasts. “Oh God.” She whispered. I wriggled between her legs, urging her to part her legs still further, as I licked and kissed at the bare skin of her upper thigh, feeling the heat from her pussy on my face. My hands slid down and pulled at her tight fitting top, pulling it upwards until I could slide my hands across the soft skin of her stomach and up towards her breasts.

I forced my hands under her bra and grabbed her tits, nipples between fingers and thumbs as she groaned. I gave her nipples a squeeze until I felt her tense, then I eased off. My nose brushed against her panties and Jen flinched. I could smell her sex, smell her eagerness. I leant back.

“Oh God,” She said, “Don’t stop.”

I leant back further, and closed her legs, “I have no intention of stopping,” I replied, before grabbing at her panties and pulling them down her legs and off over her black wedge heels.

I leaned forward again, my heart pounding in my chest, kissing along her thighs, past her stocking tops looking down at the forest of pubic hair I’d now revealed. My nose brushed through her pubes, and she gasped, “Oh Jesus.” I kissed her—over and over, I kissed her. I breathed her in. My lips against hers, kissing her, tasting her. Licking my own lips, tracing hers with the tip of my tongue. Hearing her ragged breathing, feeling her arch her back. “Oh fuck,” She rasped.

I slid the tip of my tongue along the length of her glistening slit, then puckered my lips to kiss her clit. This all felt so natural to me, even though I had never done anything like this before. I sucked on her clitoris, the sensitive nub surrounded by my lips, then brushed against it with the tip of my tongue. I could hear her intake of breath and felt her legs tighten around my head. I released her clit and slid my tongue between her velvet lips; my nose brushed against her clitoris as I started to fuck her with my tongue. “Oh sweet JESUS.”

My tongue slid further into her dripping pussy, and I lapped at her wetness, tasting her excitement, her legs now wrapped around my head. As I stabbed at her wet cunt with my tongue, my nose pressed against her clit, Jen arched her back again, lifting her arse off the bed as my tongue went deeper inside her. My fingernails raked down her thighs as I fucked her, my own temperature rising, my own pussy soaking wet. Suddenly, I felt every muscle in her body tense—as if I had given her an electric shock, she squealed and I felt her body spasm over and over, before she collapsed in a heap, whispering hoarsely, “Oh God, oh God, oh God.”

I knelt up to look at her: eyes closed, tits exposed (her top was around her shoulders and her bra askew), legs parted, and pussy glistening. She really hadn’t had to wait until Friday. I lay down on the bed next to her, spooning her, my hands wrapped around her body, cupping her breasts. “Jesus Nicki,” She said. “That was amazing. YOU were amazing.”

I put my mouth against her ear and whispered, “And I have never done that before. Imagine what that would be like when I have had some practice.”

I could feel Jen’s body laughing. My fingertips explored her body; tracing shapes across her breasts, her midriff, gently brushing her bush until she started to moan. Fingertips turned into fingernails, gently raking at her skin, her nipples, feeling her body flex in response to my touch, her moans growing louder.

I put my mouth to her ear and whispered, “I loved telling you what to do.”

“Oh yes. And I loved doing as I was told.” Pause. “Problem is, I normally have to do the telling.”

“Mmm. I see.” I replied. “So this was a change in more than one way?”

“Yes. A lovely change. A little scary, but lovely none the less.”

I leaned in closer and whispered, “So. Are you missing cock?”

Jen giggled. “No, not really. Well… not at all. You made me cum hard. Just what I needed.”

I grabbed her breast with one hand, and turned her face to mine with the other hand. I thrust my tongue into her willing mouth, feeling her groan as our tongues writhed in our mouths. Our lips parted with a smack. “But now, my dear,” I said, “You need to give me what I want.”

Jen’s eyes widened. “And what is that?”

Smiling, I replied, “Well, I still want your obedience.”

“Of course.”

“But this time, something a little different.” As I finished this last sentence, my hand was sliding back down Jen’s torso, my fingers entwined in her pubic hair. I gave a little tug, and whispered, “I’m going to shave you.”

“Oh God.”

I put my hand between her breasts, pressing against her chest, “Does that make you excited? Does that make your heart pound?”

“Yessss.” She exhaled.

“Do you wonder how you will explain your shaved snatch to your husband?”

“Mmm hmm.”

“Well, you can work that out later—can’t you?”


I stood up, took her hand and led her into the bathroom. I undressed her—leaving only her hold-up stockings on. Then I filled the bidet with warm water and had Jen sit down on it. In silence I took my nail scissors and slowly trimmed her hair down short; occasionally looking up at Jen who was watching me avidly. When her pubic hair was nice and short, I started splashing the warm water up over her pussy. Then I soaped my hands and applied the suds to her pubis. Gently I covered her with soap suds before getting a new razor. Slowly and carefully, working down and rinsing the razor often, I shaved away all of her pubic hair. When I was done I refilled the bidet with fresh hot water and rinsed her. I took some moisturizer in my hands and applied it, letting my fingers brush against her clit every so often. I knelt back to look at my handiwork; satisfied, I smiled at her.

“I wonder what he’ll make of that.” I said, “I think you look beautiful. What do you think?”

Jen looked down and bit her lip, “Oh God.”

Giggling, I said, “Well, there’ll be no hiding that from him.”

She looked at me, eyes twinkling, “I suppose not.”

Our eyes locked and we exchanged smiles. I didn’t feel like I had finished with Jen. She was on a journey of discovery with me—she was finding out about me and about herself at the same time. And I wanted to find out more about what turned her on. I also wanted to find out how far I could go—how far I could take her.

“Are you done?”

“Am I what?”

“Have you had enough? Are you ready to go home?”

She just shook her head. “Not yet.”

I smiled, “And you’ll do as I say?”

She nodded, “Yes: I have never been more excited. Or terrified.”

“Good. Then make yourself presentable. We’re going out.”

Jen went back into the bedroom, and put back on her pencil skirt, her shoes, and adjusted her bra and top so that she looked as she had done when we arrived. As she reached for her knickers, I grabbed them. “You won’t be needing these.” I said.

Five minutes later, we were walking down the street, and I took her towards the sex shop. I don’t think she really had any idea what I had in mind, let alone our destination. It was only a short walk, and when I stopped in front of the shop, she looked at me with a look of shock and disbelief.

“Are you ready?”

“No.” Jen smiled, “But let’s do it anyway.”

I followed her into the shop. It was just as sordid as I remembered it, and empty of everyone except the same bloke who had been behind the counter when I first went in months previously. I got a smile of recognition from him when he saw me, “Hello.” He said, “Long time, no see.”

“Hello.” I replied. “This is a friend of mine.” Pointing at Jen.

He looked Jen up and down, and smiled. “Hello to you too.”

Jen just smiled and nodded.

We started browsing the isles, looking through the magazines, the DVDs and working our way towards the toys. “Do these pictures turn you on?” I whispered.

“Very much.” Jen replied. “I am dripping wet, and my heart’s pounding. Especially,” she leaned forward and whispered even more quietly, “Because you wouldn’t let me wear my knickers.”

I grinned, and started looking at the dildos. Then, much louder, I said: “You know they do great deals on these dildos.” I picked out a lovely nine inch pink one and started examining it.

“Really?” Replied Jen. “What kind of deal?”

The shop assistant came towards us, grinning like a dog with a bone, “Shall I explain?”

“Yes please.” We both said, almost in unison.

“Well, we like to know that our toys are going to good homes. So we let them go very cheap if…” he couldn’t quite bring himself to say it. He glanced at me, saw me smiling. I gave him the tiniest of nods. “…If you show us how you’ll use it.”

Jen’s eyes widened. “Oh.” she said. “Oh wow.” She turned to me, staring. I couldn’t quite tell whether she was repulsed, or turned on, or just plain petrified.

She needed prompting. I held out the long pink cock to her, “It does look very nice, doesn’t it?”

She nodded, mute.

“I think you’d like it, wouldn’t you?”

She nodded again.

I turned to the shop assistant, “We wouldn’t want to be interrupted now, would we?”

He understood immediately, and went to lock the door. Meanwhile I walked Jen back to the counter. I patted the counter top twice; she knew what I wanted and lifted herself up to sit on it. I stood right in front of her, with the shop assistant looking on. Slowly I pushed her tight skirt up her thighs, my eyes locked on hers.

My fingers felt her stocking tops. It couldn’t be long before shop assistant would realize that Jen was sans knickers. Jen looked flushed, and mesmerized by my touch as I revealed her pussy. I had lifted her skirt as far as it would go. I raked at her inner thigh with my fingernails before letting my fingertips brush her exposed labia. Then she gasped and bit her lip. My fingertips pushed forward, and slipped between her lips—she was very, very wet.

I took the dildo from the counter top and slid its tip along Jen’s inner thigh. Now she really was groaning in anticipation. Then the tip of the plastic cock rubbed against her clit, “Oh God.” She whispered. I slid the dildo up and down her slit, testing it ever so slowly between her lips. Little by little, I edged the cock inside her. I sensed movement out of the corner of my eye—when I looked across, the shop assistant had taken out his cock and was wanking away furiously.

As I looked back at Jen, I saw that she too had realised what he was doing. Then she closed her eyes and her head flopped backwards, as I pushed the dildo deep inside her. I leaned in close and whispered, “No need to wait until Friday after all.” I slid it back out almost the whole way before ramming its full length back inside her. How she squealed! Slow thrusts, getting faster and faster, longer and deeper; Jen leaning back, arching her back, eyes closed, erect nipples making little bumps in her blouse. I knew she couldn’t last much longer. Soon she was panting in time with my thrusts; my free hand moved to her clit; first I rubbed it then pinched, pulled and twisted it until I could feel her body tense. All of a sudden she let out a scream, and her legs clamped around my hand, holding the pink cock deep in her dripping cunt. Moments later, her stockings were splattered with shop guy’s cum. As Jen came down from her high, I gently stroked her hair, caressed her cheek, leaving her impaled on the dildo.

I turned to the shop assistant, “I think she’s earned this, hasn’t she?”

He nodded in response and slipped his shrinking cock back into his grubby trousers.

I slowly slid the dildo out of Jen’s now gaping snatch and gently eased her legs back together, then pulled her skirt down. I took a tissue from a box behind the counter (can’t imagine why they had them there) and wiped the cum from Jen’s stockings—aside from the ecstatic expression on her face, you’d hardly know anything untoward had happened.

With the dildo tucked away in a carrier bag, we were soon walking back towards my flat.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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