Teaching Her How To Please Herself

I was 26, she was 20. We were coworkers in a busy restaurant kitchen. Being on the line and relying on each other to succeed builds a strong level of trust and friendship. You get close to your teammates. That sometimes leads to relationships.

Steph and I worked side by side and got close. It took for almost a year before I was brave enough to ask her out. She stood me up on our first date with a reasonable excuse ughhh lol. Second date I tripped on the step up from my sunken living room and broke my toe getting her something drink from the fridge.

 There were a few more dates after that were equally ridiculous. Showing each other that we could laugh together and not be petty about the things life throws at us led to romantic love and a physical relationship.

The first night we spent together neither of us knew what to say and just got lost in, mostly clothed, romantic kissing and cuddling. The second night was fun new lovers clumsy hands inside underwear sexy. I’m a big fan of foreplay but, she was rushing to intercourse. I didn’t have protection so we agreed to dial it down and wait until the next night. 

We picked up some condoms the next day and quietly verbally teased each other all night at work. By the time we got into bed we were both hungry for each other. It didn’t take long for us to get our clothes off and feel our naked flesh pressed together. I knew she was less experienced than me but as my hands cautiously explored between her legs I got reactions of surprise that made it seem like she wasn’t accustomed to being touched in a way that prioritized her personal pleasure. I loved being able to illicit those kind of responses from her and was excited to please her.

I spread her outer labia with my left hand and used my thumb and index finger of my right hand to slide all the down her hood on the sides of her clit until I could gently pinch her inner labia and slowly pull them down towards her vagina. The slow soft downward tugging of her inner lips stretched her clit downward and I could feel the increasing pressure I applied get her clit hard for real. Using her own flesh wrapped around her clit, I stroked back up with more pressure. Her back arched for a second and she let out a deep moan. At the top of the next stroke up, I pulled her hood back as far as possible and exposed the hard bud of her clit.I l put my middle finger in my mouth as lubricant and I used my left hand to spread her lips and pull her hood  farther back exposing as much of her erection as possible. I used my wet finger to trace a line from her vaginal opening till it brushed the cleft on underside of her bare clit. Her body spasms and the sound she made reminded me of the first time a girl wrapped her mouth around the tip of my cock. Something feeling so good that you feel like you should be in trouble for feeling like that, so overwhelming that you can’t take it while simultaneously wishing it would never stop. I could feel her clit tighten and try and retreat inside her as she uncontrollably pulled away.

A few deep breaths later she was hungrily groping me. Her hand went between my legs and I knew very quickly she had no idea what she was doing. Her touch was rough and her  effort caused more pain than pleasure. Thankfully she asked me to put on a condom and initiated intercourse.  

Even at that age I had great stamina and pacing. Eventually I had to ask her what she needed to cum because I was edging. She was very confused. She had been with 3 others before me but had never reached orgasm. She thought for women it just felt nice and only men cum. 

I decided we should stop and talk. 

I asked her if she’d ever masturbated to orgasm. She told me that she had touched herself in ways that were comforting and pleasurable but the best it had ever felt was what I had just done to her with my hands. She thought she was doing something wrong and was bad in bed because I hadn’t finished yet. 

I explained I was waiting for her to go first but, she had no idea she was capable of orgasms. 

She said when I was touching her was the first time someone’s touch made her feel a need she didn’t understand how to satisfy. 

I asked if we could relax and cuddle while I touched her and talked to her. I got an enthusiastic yes. I kissed her, my lips on hers, on her neck, her arms, I cupped her breasts as I kissed her belly. My tongue found her nipples as my hand was caressed her inner thigh. As her breathing became deeper and faster I let my finger between her lips to open her. I talked to her in a whisper about every part of her I was touching between her legs and how they are all connected. Where nerve endings are concentrated. How most women use their clitoral hood to indirectly stimulate the clitoral shaft, usually favoring one side of their clit. How the inner labia connect to the clitoral hood and why pulling on them feels so good. When she was soaking wet I put my fingers inside her and put gentle pressure on her g-spot and talked about a large unseen structures of the clitoris that can be stimulated from inside. 

I started talking about what it feels like for me as I masturbate from the first moments of desire starting with fantasy as a pleasant touch slowly grows into the increasingly wonderful sensations that I want to last.

Talking about my experiences with masturbation made her very wet.

 I slowly increased my pressure and speed against her g- spot until she was moaning. When I felt her first involuntary contraction squeezing me I took my fingers out and put my head between her legs. Her clit was long and thick, making her swollen glans peak out from under its hood. I teased the whole shaft with my tongue until both of our juices made her slippery. I moved back up to kiss her as I used one finger to stroke the left side of her clit up and down, occasionally letting the bud of her hard clit roll under my finger and brush her glans. 

Her noises and her body language let me know she was on the edge. I put her hand over mine so she could feel what I was doing, then l removed my hand like training wheels from a bicycle and let her hand and arousal do the work.

I told her she was probably going to feel like she had to pee but just to keep going with it. Soft kisses, sexy talk and encouragement had her hand  going faster and faster between her legs. She began to stiffen and was making sounds of need. I could see that she was feeling some embarrassment.  I reassured her there was nothing to be embarrassed about. I told her it meant a lot to me to have her trust and letting me guide her through the experience and that her pleasure was very sensual and arousing. I asked her to keep going and not stop, to shut everything out and get lost in it. 

She continued and her toes began to point and she started to press her legs together. I knew this was it. Before her legs could close I got my hand between them and slipped two fingers inside her. As her thighs pressed together, closing her clit between her puffy lips, I moved my fingers inside her going faster and faster until I matched the pace of how furiously she was rubbing her clit. 

The sounds she started to make were loud pleading whimpers. Her back arched, I think she tried to say OH GOD, what came out was more like UGGGGUDDUHH. I immediately pushed up again her g-spot with a lot of pressure.

Then it happened, her head turned left to right quickly a few times, her eyes  opened wide as her head tipped backwards. Her heels and her shoulders pushed her ass into the air, her mouth opening and closing in a silent scream. 

Her orgasm hit hard, her tight contractions pushed my fingers out of her and I could see her belly spasm with the rest of her contractions I could no longer feel. Both her hands went between her legs pressing against her vulva as she curled into a ball and shook for 20 more seconds of orgasmic bliss. 

I didn’t get to cum that day but being part of her first orgasm was better.

Like all of us, after that first orgasm she was hooked. The next night she told me how great it was but didn’t think she would have climaxed without my fingers inside her. I told her won’t always be the case but it doesn’t hurt to have a little push over the edge. I could tell by the way her body responded when my fingers were inside her that she was probably capable of g-spot orgasm without any direct clitoral stimulation. I asked if I could try and I got very quick YES answer. We made out, I talked about how hot our experience the night before was, how much I appreciated her sharing that with me.

Cuddling led to gentle touches between her legs. I teased my way in between her lips until they spread with arousal. I touched every part of her that could make her clit tingle without ever directly touching it or her hood. When she was starting to drip with her wetness I made small slow circles around her opening working my way inside. Every little bit I went in I would pull out and go deeper the next time. Her hips began to push against me and I let them take me deep. I worked my way out till I was at her g-spot and cautiously used two fingers to massage it until she reached the point of arousal where her inner and outer labia spread flat and her vagina opened wide with invitation. I pulled them out to tease her clit with feather light touches. When it began to steadily pulse I put my fingers back inside her. She was wide enough now to easily take 3 of my slender fingers. I used my middle finger directly against her g-spot  and by spreading my index and ring fingers I could stimulate the large internal structures of the clitoris hidden inside her that exist to the left and right of her visible clitoris. The moaning said I was definitely getting this right.

She tightened from stimulation, pressing my fingers back together. I asked told her to try and breathe only through her mouth so her diaphragm wouldn’t contract and stay as relaxed as possible.

I told her it was probably going to take a while but not to try and rush it. I told her to let me know about what pressure and pace felt best. 

Gradually I increased pressure and speed, she was getting tighter now and trying not to squirm. There were a lot of sighs, moans, oh yes and oh god yes until she asked for harder and faster. I put my left hand on her abdomen so I could feel any deep contractions of her cervix or uterus and so I could pull her vulva up and put some tension on her clit without touching it. 

I found a pace that was making her build and kept it, reassuring her that the orgasm would find her. When she started begging for more I told her I was fantasizing about her orgasm last night and how it reminded me of my first orgasms when I couldn’t stop my hand from moving even though the feelings were  overwhelming.

I told her I was going to get her there and fulfill her need.

 I pressed myself against her leg, the steady throbbing of my erection making it physically clear that I wasn’t just pretending how aroused I was with her pleasure.

 I mixed my pace to tease and edge her out. She started to try and press her legs together so I had her sit up a little so I could change my angle of insertion and straddle one of her legs so I could keep the other apart with my knee. I switched to two fingers and went faster and faster. 

The Yes! Yes! Yes, Oh God Yes’s were mixed with Please don’t stop’s. She started to tense and I told her I would stop if she didn’t relax and breathe. I reminded her that she knows what an orgasm feels like now and asked her to close her eyes and let me know when it’s very close. 

I kept the pace until she said she, “Baby!, I think I’m going to cummm!”  I stopped for just a couple seconds, long enough for her to quietly say, "Noooooo." 

Then with less pressure and a much slower and steadier speed I resumed. She said ohhhhh fuck and shivered. Her eyes were closed and her mouth was wide open as she tried to breathe around moans, gasps and the involuntary noises of ecstasy. 

I told her I could feel that she was almost there and to stay relaxed so it could overtake her. Shortly after she said, “ I think, I think, I think!”. Then, ohhhhhhhhhh.

 I knew this orgasm would be different than her touching her clit. 

She said, “ I’m, I’m, I’m …" .and then a huge sigh. Her body relaxed and I felt a warm gentle squeeze against my fingers.

 I asked her what she was feeling and she said felt like she was floating in space. 

She was moaning so soft and breathy. At least 10 more of those gentle squeezes hugged my fingers and then I could feel her tighten and the top wall of her vagina bloom and flatten out, she whimpered, “ I think it’s cummminnnnggg, oh god, I don’t……….?” 

I kept pace and she melted peacefully,  inarticulably moaning for about 15 seconds then with a sharp intake of breath and a loud Oh God !Fuck!  Her pussy convulsed and ballooned and convulsed over and over. 

Thick cream flowed all over my hand and out of her. Her clit bulged purple and throbbing out of its hood like it was going to explode then retracted and shrank under it still pounding. I started to slow down thinking it was over but she grabbed my wrist and said, “ PleaseDontStopp!”  She must have orgasmed for over a minute.

Breathless we cuddled and she wanted to please me but, I was enjoying the tease and so excited to be able to watch her first time pleasure. We had the next day off so I told her we could get to me later. All I could think about all night was the experience.

 We slept in the next day. Went out for lunch but we were both anxiously waiting to be back in bed. 

Later that afternoon we were. 

We talked about the night before and she told me at a certain point it was impossible to know where I was touching her or what my fingers were actually doing.

She still wanted to please me and help me feel something like she had the last two days. I told her I wanted to see her pleasure one more time first but this time her solo and let me try and guide her through it. She agreed on the condition that I would show her exactly how to give me a mind blowing orgasm after. I’ll write the story of how she fulfilled her commitment to making me cum and why there is a hand mirror beside my bed, later and in a different story.

I asked her to strip to her panties and find a comfortable position where she could be sitting up enough to watch the things I would be asking her hands to do between her legs. We began.

I asked her to take her hand and caress her mound over her underwear in different ways. Without parting her outer labia, using her fingertips in a slow back and forth motion starting from her perineum to her belly up to her mons Venus or having her cup her whole vulva in her hand, gently pressing against the opening of her vagina and using the heel of her hand to put different levels of pressure against the unexposed clitoris between her lips.

I asked her to mix in a tease the inside of her thighs and let her fingers slip under the elastic to touch her outer labia. 

While she experimented I talked about how I enjoy the changes my body goes through as my arousal grows with a slow building erection that lets me feel every pleasurable subtlety of its growth until I can coax an orgasm out of it, or the immediate rock hard erection that has every nerve ending tingling so much that only a few touches make me cum.

As I saw physical signs of her arousal beginning I asked her to slowly use 3 fingers to stroke her vulva up and down from mons to ass, using her middle fingers to trace the slit between her lips. It didn’t take long for her labia  to engorge.

I grabbed the hand mirror so she could watch with me as her outer labia began to flatten out and the slit between them grew visibly wider through her underwear. Her lips slowly filled the crotch of her panties trying to flatten all the way out against her thighs and her juices were  making a wet spot through her panties.

The shape of her hardening clit became clearly visible through her panties. I asked her to start at the top of her hood and press all the way down it with a gentle pressure until she reached the bud and start from the top again. 

It was obvious her body liked that. I could see it pulse with every touch. Her clit grew and in a stroke, as she tried to put pressure back down on the hood, her finger rolled off it and pushed it hard to the side. She moaned, I moaned and it was time for those panties to come off.

I showed her in the mirror how her inner labia connected to the hood of her clit and its glans. I had her grab them together and individually with gentle tugs to aggressively pulling, trying different directions and finding what feels good. She pinched them both between her fingers and pulled tightly downwards stretching her hood over her hard clit towards her vagina. I suggested she flex her pelvic floor muscles at the same time. I could see her clit rub under its hood as her flex made it try and stiffen.

I had her pull her labia all the way up so her clit was free of her hood and she could see it standing tall even without the mirror.

Her wetness had been steadily flowing out of her so I asked her to put her fingers inside her and use it’s moisture on her clit. We experimented with so many ways of clitoral stimulation. I could feel her need growing so I just told her to relax, use what we were learning to find what felt best to finish.

She settled in to a familiar female pattern of her middle finger shuffling left to right using her hood to indirectly stimulate her clit faster and faster. 

I let my hands pet her thighs, her belly and her breasts as she went to work. I could see her getting close and alternated soft flicks of my tongue across her hard nipples with warm breathy kisses on her neck.

 I was encouraging her to finish when she stopped and said she wanted to try use her fingers inside her to cum.

I showed her what motions I was using with my fingers and assured her it would be easier for her to find the right spots and chase them than it is for me. I showed her how I’d use faster and shorter movements with my fingers when her pussy was super tight and how I’d use harder and more pinpoint pressure to keep the spot or how when she would flatten out inside how I’d use much longer strokes from deeper inside her slowly increasing pressure towards her g spot. Basically just adapting to how her body was responding.

She slipped two hesitant fingers inside her. I showed her how to angle her wrist from her position so it felt more like the angle I used and could allow comfortable access for her other hand to stimulate her clit simultaneously. I showed how with one hand the heel of her hand could press against her clit while she was fingering. 

She really wanted to try and cum without direct clitoral stimulation. 

I suggested instead of trying to exactly replicate the technique I used to draw an orgasm out of her to play, tease and do whatever feels good.

I encouraged her to look for the Orgasm or chase it, but to have faith the her orgasm would find her. 

I showed her how I would circle around and tease her opening. How to let her fingers go in a little further every time and then suddenly going deep. That even if she didn’t want to focus on a clitoral orgasm, she could still let her fingers slide over its shaft on their way inside. That she could let her fingers push her inner labia inside her and pull on her clit. 

She closed her eyes and played. I watched her experiment until she found what worked. I could see her intensity as her pleasure increased.

 Eventually the oh Gods and Yesss’s started. 

She breathlessly said she was really trying but couldn’t stop touching her clit. I told her that it was ok but she actually wasn’t touching it at all. 

She opened her eyes and looked down and in disbelief saw, even though she could feel it, there was nothing touching her clit. She was still watching when she found a good place inside her that saw her clit rhythmically throb. That closed the deal. 

Her fingers moved with purpose inside her. When her back arched I put one hand under her ass and the other on her abdomen so she didn’t lose pace or pressure. I felt the orgasm in her belly before I could see the look of impending release show in her face right before her body spasmed and made her hips thrust upwards over and over. Watching her clit throb to the beat of her orgasmic pulses made my erection try to pulse in unison.

She shook until her shuddering turned into relaxed deep breathing in my arms.

When her afterglow subsided, I showed her how to appropriately touch me without lube and then with. I described the highlights of my arousal as I was watching her as she skillfully brought me to climax for the first time. That part of the experience to follow in the next story.

We had so many amazing sessions after that day. I’ll write about some of them later. We were both invested and fascinated with each other’s pleasure. To this day I’ve never had another lover that I could be that open and experimental with.  I’ve had a few comparable powerful orgasms with a couple other people but, nothing that has satisfied me mentally, emotionally and physically in the same way.

Eventually life moved us in different directions and our relationship ended. 26 years later we are still friends. We’ve only talked about that part of our relationship once but we were both clear that our past sexual relationship is irreplaceable and still plays a consistent role in both of our fantasies.