Awakening a Shy Friend's Sexuality

"So...you're sure about this? This is what you want?"

She looks at me with her sultry eyes, slightly hidden by her raven black hair. Her eyes drop away as I make eye contact, before finding courage to re-connect our gaze.

"Yes." She says, though there is a slight tremble in her voice. "I'm sure. It's what I really want. But I worry I'll get nervous when we get there, and I'll be too embarrassed, and then you'll be angry, and I'll...."

"...I won't be angry" I interrupt her. I take another sip of my cappuccino before continuing talking.

"We go as fast or slow as you want. You say stop, we stop. And if you're really too nervous we just sit on the bed together, fully clothed, and watch a movie on my laptop. OK?"

"OK." She replies. A smile goes across her face, but she is smiling to herself, not to me. She takes a sip from her tea with two hands, her thin wrists shaking slightly. "Next Saturday".

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The girl is called Samantha, or Sam for short. I met her online almost 2 years ago. She was 20 then. She's 22 now. Her sweet but sultry face attracted me firstly, but her bio really got me interested. She's the most confusing person I've ever met. It's been 2 years, and I've only managed 3 dates.

Sam writes erotic fiction. Mainly male/male, but sometimes straight and lesbian. She sells the books online, and is popular enough in her genre to do that full time. However, she is also the world's most shy woman, and...a virgin. All day she writes about cocks, but has never seen or touched one in real life.

We built up a strong friendship online, even though we are both sure we are not 'the one' for each other. I've dated other girls in the 2 years, but still kept my friendship with Sam. Now I'm single, and so is she.

At her request, 3 weeks ago, we had her first kiss. We had planned it, talked about it, and then we kissed. Her soft lips were gorgeous, and I instantly wanted more. But I didn't press things. She's very nervous about men. And that's very fair -- I am 30.

We kept talking online, and she felt braver after the kiss. She said it helped her writing. "How do you write about cocks and sex all day, if you've never had sex? Never held a man's cock, or felt what it's like to have a dick inside you? Isn't it almost impossible to write porn as a virgin?" I asked her on our first real date, over a year ago. "I've got the world's dirtiest imagination," she said, with a slightly out of place confidence. "And porn. Porn shows me how it looks like. Then I put that into words."

"It's not the same." I tell her. "Porn is acting. It's not real sex. And anyway, you don't know what a cock tastes like, or what it smells like in a room after sex. Or how it feels all over your entire body when you orgasm."

"I have toys. I know that one" she says playfully. Her eyes meet mine, and I realize she has the most sexy, seductive eyes I've ever seen on a woman. But she's never used them on a man. I think to myself that she could have any man she wanted, just by using those eyes. But her shyness is a barrier to her.

"Well," I told her, at our first date. "If you ever want someone you can trust, to help you explore your sexuality, you can talk to me. Maybe we can make that happen."

I said that over a year ago.

Last week she messaged me, asking if that offer was still there. I'm single, so I suggested we talk in a coffee shop about it. I think that fills you in on the details.

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Next Saturday, and I meet her near the underground station, and start walking her to the hotel room I've booked for the evening. I'd already checked in as soon as I could, so we would have lots of time in the afternoon together. That way if she gets nervous, it's easier for her to leave.

"You're family OK?" I ask, making small talk as we go.

"Yeah. Mum knows what I'm meeting you for. She's super supportive. Dad and my little brother just think I'm staying over at a friend's tonight."

"That's not a lie" I reply back, smiling. I notice the beautiful dress she's wearing, even though it's a cold day.

We go through the lobby and up to my room. It's on the 3rd floor. It's nothing super expensive, but it's not a cheap travel hotel either. It's still quite a small room though, with just the bed and bathroom with shower cubicle.

As we go inside, I immediately see her body posture become uneasy. I realize she's seen the double bed. I take her coat and her bags, and then walk over and sit on the bed, fully clothed.

"It's OK. Let's relax. No pressure for anything." I pull my pre-prepared laptop up, and set it on my knees. "Let's watch a TV show together. Maybe Big Bang Theory, or True Blood?"

She moves over, and carefully sits next to me on the bed. She still has her arms folded defensively. We sit and watch an episode of Big Bang theory, and over the episode, she begins to relax. As it ends I see her beginning to panic, so instantly put on the next episode without asking or making a big deal. Soon she is laughing at Sheldon and relaxing into herself. I hold her hand through most of the episode.

When it finishes, I fold up the laptop, and kiss her lips. She doesn't seem nervous, and our kiss becomes more and more passionate. I feel her hands start to move over my body as our tongues begin to dance within our mouths. Already the passion is building in me, and I feel my cock beginning to rise.

I pull away gently from our kiss. She resists, clearly enjoying our moment, before returning to her seated position. I stand, leaving her still on the bed. "I'm going to get naked now. So you can see what a naked man looks like. OK?"

She nods. I watch for signs of discomfort in her body language, but she seems fine. Slowly, I undress before her, first taking off my jumper and shirt, before moving down and removing my socks and trousers. Finally, I remove my underwear. My rock hard cock is staring straight at her.

A smile creeps over her face, and I know this is what she wants.

I lay back down, next to her on the bed. Her hands move tentatively over to my cock. "It's OK" I tell her. "You can touch. You can feel. You can even taste it if you want."

She wraps her hand around it. "I can feel your blood" she says surprised.

I just smile and nod.

She starts moving her hand up and down over the cock. First it's slow and gentle, but suddenly she speeds up, gripping too tightly as she does.

"Wow! Slow down. Be gentle." I reply. She recoils backwards, releasing me.

I take her hand, and place it back onto my cock. I wrap my own hand over hers, and help her find a good rhythm. Her soft hand, now going at the perfect speed, feels so wonderful over my cock. I fear I'm going to cum already, so I move to kiss her, and move her hand away at the same time. We kiss passionately, and I begin moving my own hand towards her breasts, but she instantly becomes uncomfortable again, and breaks the kiss away.

"Sorry," she says meekly. "I'm not ready for that yet. But I want to spend more time with your cock. Can I taste it?"

"Sure," I reply, and stand up, walking over to her side of the bed. "But I'm already very close to cumming. You're hand felt really good. I'll tell you when I'm close."

Without saying anything, she puts her whole mouth over the cock. The warmth of her mouth feels so wonderful. I feel her lips at the base of my cock, and her tongue playing with the shaft. At first I feel her teeth touching me, but then she opens her mouth wider, and starts sucking me up and down. She doesn't take the cock out, she just focuses on the sucking, going up and down. It feels so wonderful, and I close my eyes to focus on the feeling. After a minute I open my eyes again to see that one of her own hands is now between her legs, playing with herself through her panties. The sight is so sexy, and so wonderful to me. I feel so pleased that she's doing this, opening her sexual side up in front of me.

I feel myself beginning to shudder inside, preparing to shoot my load. "I'm going to cum" I warn her, but she doesn't stop sucking. "I'm about to cum" I warn her again, but all she does it look up into my eyes with her sulty, dark eyes and makes long eye contact as she keeps sucking. My cock explodes within her mouth, shooting load after load inside her warm cheeks. She doesn't flinch, and takes it all inside. When I've finished, she finally moves her head away, and spits my cum into a nearby glass.

"You felt wonderful" I say to her as she finishes spitting my juices away. My cock is already flaccid.

"It tasted different to what I imagined" she replied. "I think I'm going to have to re-write some of my books."

"Maybe just edit." I say, as I sit next to her on the bed. I can't help but look down at her crotch. Her panties are soaked from where she was fingering herself.

"Sorry" she says, when she sees I've noticed.

I move over and kiss her neck sensually. "Don't be sorry. It was beautiful for me. You looked so sexy. It's what made me cum. I wanted you so much right then."

She kisses my neck in return, and I move my hand up slowly from her knee, to her thigh, to her wet panties. I start to massage her through the cloth, and I feel her stop kissing me as she focuses on the pleasure. I look at her face, and see she's closed her eyes, focused on the feeling of my fingers as they make small circles across the cloth. She arches her back as I go faster, putting gentle pressure on her as I continue my massage. "Oh gosh" she whispers.

I move to kiss her neck again as I continue my massage. She puts her hand over mine, and guides my hand, showing me exactly how she likes it. My other hand moves to her breast, cupping it over the dress. Suddenly I feel her shudder, and she pulls my hand away as she brings herself to orgasm.

She collapses backwards, laying down onto the bed. I put my head down too, looking at her. She turns round, so we are face to face. I can see a drop of my own cum still on her lips, so I don't go to kiss her. Instead, I just enjoy seeing the post-orgasm smile on her face.

"Thank you for letting me share that with you" I say. "Are you ready for me to see you naked?"

She hesitates. "I think so, but I don't want to undress in front of you. Maybe you could turn around?"

I think for a second before replying. "How about this. Why don't you go into the bathroom, and have a shower. That way you've be naked, without having to strip in front of me?"

She agrees, and walked away, into the bathroom. The room is not very soundproof, and I hear a splash of urine in the toilet, before hearing the shower being turned on.

I go to one of the bedside draws, and pull out supplies for the next part. A couple of condoms, some lube and my own, small sex toy. A cock ring with a little, detachable vibrator. I place them on top of the bedside cabinet, along with a bottle of water.

I open the door slowly to the bathroom. There is plenty of steam already. She clearly enjoys a hot shower. "May I join you?" I call out softly. I hear a gentle 'uh huh' noise coming from within.

I open the shower cubicle, and see Sam, gorgeous in her nakedness. Her boobs are slightly larger than I expected, and realized she always keeps them bound and hidden. I also see her pussy for the first time. It's small and beautiful, shaven around the inside lips, but still with a little hair nearer the top. She moves to cover herself as I walk inside the cramped shower, but I kiss her, and move her arms away gently. "You're beautiful." I sensually whisper in her ear, before moving my lips onto hers again.

As we kiss in the falling water, I feel my cock rising again. She moves her hands gently over it, lathering it with shampoo. I move my own hands over her breasts and round her back, learning her body and curves. I pull her closer to me, and kiss her again, as I move my hand round to hold her ass. My cock presses into her stomach as we kiss in the shower, and I move my hand right round, to tickle her pussy from the back. She feels me, and kisses me harder for it.

The pressure in the shower suddenly falls, the water change breaking our moment. We finish washing ourselves in a more practical, less sexual way.

"You have a really nice cock." She tells me as we dry ourselves off. The bathroom mirror is steamed up, and I draw a smiley face on it as she finishes drying her hair.

"Thank you." I reply. "Are you ready for the next stage?"

She looks at me with those beautiful eyes, and it feels like she can see my soul as she does. They look at me with a confidence I've never seen in her before.

"Yes. I'm ready. You can stop asking me now. I've decided. I'm ready. I want this."

That's the moment I've been waiting for, and I take her hand in mine and lead her out of the bathroom, into the bedroom again. I guide her to lay on the bed. I kiss her lips again, before walking away, to the foot of the double bed.

Slowly, like a tiger, I creep up the bed, moving my head between her feet. I kiss both gently, before moving my head and body further up. Now I kiss her thighs. First the left, then the right. Her legs start raising up in anticipation. I move forward again, planting kisses on her inner thighs, before fully moving my body onto the bed, crouching before her. I kiss the small mound of hair about her pussy. I can smell her already, and it excites me so much. I move my lips down, and start slowly teasing her labia with my tongue. I glance up to her face. Her eyes are shut and she is biting her lip. I take it as a very good sign, and continue playing with her pussy. I move my tongue around her clitoris, making a slow circle. Then I bring the flat of my tongue down, then up her whole pussy, trying to touch as much of it with my tongue as I can. I can taste her juices. The heady musk fills my tastebuds, but I also pick up a citrusy taste, like oranges on a sunny day. She tastes wonderful, and I dive my nose straight down, and my tongue probes to find her entrance. It doesn't take long, she is dripping wet, and I feel it begin to drip down my chin as I lap and lick and gently suck on her lips and clit. Her moanings are soft but continuous. After a couple of minutes I move my mouth exclusively to her clit, and slowly insert one, then two fingers inside her. A sudden loud moan as I hit the perfect spot in her pussy. She tightens around my fingers, and I know she is ready for my cock. I pull away from her as her whole body shakes in orgasm. I walk to the bedside table, and roll a condom down my penis.

She's calming down now, and looking at me with a contented smile on her face, her legs still akimbo. I pull her towards me, to the edge of the bed. We make eye contact, and there is a wanting deep inside her eyes. I put my cock to the entrance to her tight but wet pussy, and slowly push it inside her.

I push myself as far as I can, then let it sit there for a second, allowing her to get used to the feeling. There was no blood, or any sign of discomfort from her. Slowly I begin rocking back and forth, building a gentle rhythm. Her body starts matching and grinding with me.

"Oh.." she says quietly, unsure if she should speak during sex or not. "...It's so natural. My body knows exactly what to do"

"Yeah," I reply, looking down at her smiling face as I keep sliding in and out of her. "It's primal." At that, I begin to speed up. "It's wild." Again, the speed of my strokes increases. "I'm an animal"

At that, I push her body backwards, back onto the main bed. Her head on the pillows again, I lay on top of her and kiss her passionately, while pushing myself into her again. She almost bites my tongue during the kiss as I push my cock deep into her pussy. She wraps her army and her legs round me as I push into her. I move my face away from hers, and down to the neck. I mean to bite gently, but can't help putting force into it. I hear her yelp in pain, and stop suddenly. But she just whispers... "Don't stop" and in return starts biting my own neck.

We're animals, biting and clawing at each other's backs as we fuck. I can feel my orgasm building, but I'm not ready to end our session yet.

I climb off her, and lay next to her. "Do you want to try on top?" I ask, smiling at her. Her neck is red from my bite marks.

She slowly climbs on top of me. I get the most beautiful view of her sultry eyes and firm breasts as she lowers herself carefully down onto me. She leans back as she starts building her own rhythm. It's much slower then I had been going, and I see from her face she is focused on every feeling, trying to put into future books the feeling of my cock filling her moist pussy. I look over my shoulder at the bedside table, holding the lube and cock-ring. No need for them right now.

Her slow, steady beat feels great, and though calming at first, again I can feel my orgasm building. It won't be long now.

"I'm almost there" I tell her. She says nothing, but looks deep into my eyes, nodding her head softly.

I lean my body up to her, grab her body, and role her over, my cock still inside. I'm on top of her again. However this time, I fuck her gently...tenderly. The moment has come, and I look deep into her eyes as I feel my cock squirt inside the condom. I shudder all over and my weight falls on her as I give in to my orgasm. I say nothing for a minute, laying on her, until finally I feel my cock beginning to relax and start contracting. "Thank you," we both whisper to each other.

I roll off her, and fling the condom away. I move to hold her in my arms. We spoon, naked above the covers.

A few more minutes, and she gets up to go to the bathroom. She looks out the window as she leaves my embrace. "It's dark outside."

I glance at my phone. 1.34AM. "It's late. Or early. Are you still happy to stay the night?"

She nods, as she walks into the bathroom. She showers herself, but I'm too tired. I pull myself under the covers. Already my eyes are drooping. She rejoins me, this time under the covers. She kisses my neck, pulling her body around mine.

"That was wonderful. You made it so special for me. Thank you."

"I enjoyed it too you know," I reply sleepily.

"Good." She replies as she snuggles up to me. I can feel her breathing, and her chest as it rises and falls. "Because I want more in the morning."

"I can do that." I answer, as my eyes close and sleep finally takes me.