by Cynicole

chanced upon your webbie and it’s funny how i’ve wanted to know if my gf and i were the only ’strange’ ones in the world, and there i read these experiences by others.

ours is very similar but add another ‘taboo’ we broke: she was my student.

there’s a 21-year gap (18, 39)  between us and till date it’s never really been a problem because while i’ve never really grown up and acted my age, she has a very aunty-like demeanour which makes her seem so much older than her age.

we had to skirt around this of course, not because of the age but the fact that she’s still in the school i teach. but outside, we could pass off as any girl couple. we do the average things together, groceries, dinners, overseas trips. except that when she’s busy with her studies i’m with my teacherly duties. we share the same school hols so that helps the timing heaps.

we’ve been in this r/s for more than a year and so far it’s seen through many ups and downs, not because of the gap but usually because of the usual misunderstanding, pms-induced often. haha

we do have great plans ahead. i have 2 young kids (8 & 10) so it kinda makes the circumstances a little more challenging in time. to them she is like a big sister. to me, she is my significant other. she understands me despite our very different experiences and when we’re holding each other, it’s really just two souls connecting.

the age-gap only becomes an issue when we’re out and socially i have to introduce her, or tell peeps how we met. usually we have to censor because of people’s limited comfort level with this. but like the other stories here, she gives me a renewed sense of living with her infectious optimism while i ground her with my nurturing ways, e.g nagging her to complete her assignments.

anyway, i hope our story can inspire others who question the possibility of pairings. i know that having surpassed so many phases of self-doubt that things can work between two people when there is trust, love and communication, regardless of age, gender,status.

By Orlando 

I’m 30, and I am hot for and fond of my friend who’s twice my age. I can’t believe this. She’s 60, and I feel such a crush… I am so into her body, I could die. She looks really good, she’s strong  and assertive and yet she’s sweet and sensitive. We have a lot in common and we do not feel the age gap. We spend so much time together, we call each other for nothing and support each other. She’s been divorced for more than 10 years. I have no hints that she likes women.

It’s been 8 months now since we’ve become friends. It was quite intense from the very beginning because of the context. But then it didn’t go away, and we became closer because we have a lot in common. So it remained intense and now we’re so close I can just pop in or call without saying it’s me, and be very casual, like with a family member. It’s become more intimate. Also I can sense there’s a common attraction… But I can’t tell if it’s on the same level… Because as far as I am concerned, I could go to bed with her. But I could also be happy with just my arms around her, or the permission to kiss her. ANything, but a physical touch, something that could express the deep affection I have for her.

She’s asked me to come with her on trips… It turned out it wasn’t possible for me. But just thinking she’d have me come along was strange… Should I plan a week-end once and invite her to join me? See what would happen?

I slept at her house, but of course, she told me to sleep in the guest room… But the next morning, she woke me up and walked into the room to do so, and said she’d make coffee. When I came down, she was in a beautiful gown. It drove me crazy to sleep in a different room.

She’s always known I am a lesbian. We’re referred to me being a lesbian and it sounded like she was a bit excited by that. She never asks me about potential girlfriends or lovers I might have. I’ve tried to make her curious but she asks no question, which is weird because she asks me about everything else in my life and it would be quite natural.

We see each other once a week, we call eah other very often during the week, like once every two days. We also call for no reason. There was that one time when we called each other everyday of the week. I thought it was a bit too much but she welcomed it, and would hang up saying “well, talk to you tomorrow!” She asks me if she looks good. She is a gorgeous woman but I guess she feels older and wants to still be attractive. I compliment her. I was shy before. But now I’m less shy. The other day I said something twice and both times she blushed and looked down. And I added I never flatter anyone, I always tell the plain truth.

I even gave her a really cute t-shirts with a huge compliment on her printed on it. She had been joking about that thing, that was a surprise I was preparing for her. But when I gave it to her, and was silent, smiled, but weird. She kissed me to say thank you. But her reaction was strange and I was afraid she was embarassed now, and that it went to far for her. Then later on, we mentioned it, as I joked around. Anyway I thought I went too far. But yesterday, she told me she’d been wearng the t-shirt to work… and that she was proud. So, now I interpret her reaction differently. I think she was moved, and that’s why she looked at it in silence and looked away.

Many times I feel like the connection we have is almost like flirting. We tease each other, I joke around. I know why I do it, I do it (the jokes) because I’m dancing around her.We’ve spent a lot of time. She’s a very busy woman, but even if she’s busy, she asks me to just come along with her. So I’ve spent whole days with her, running errands and even going to her work place, helping her and laughing all day.People see us and don’t really understand who I am. Some of her friends her age, I noticed were surprised to see me the first time, then a second time and a third time again with her, and the age gap is the main reason I think.

We have spent whole days together, done the craziest things. and she amazes me because she has so much energy!!!

We have moments when we talk and I feel a gaze, or flirting. But I don’t know if I’m imagining it. The other day, she had a very nice tank top and I could see her beautiful round arms, her shoulders, and when she squat down, I could see her beautiful breasts in a beautiful sophisticated bra (she has them in every colors depending on the color of her shirt)… My eyes dived in her cliveage. I know she MUST have noticed. I she have because she was looking for something her bag, and my gaze was travelling from her eyes, the inside of her bag, and back to her breasts. And still, she kept looking and me, smiling.

I dream about kissing her, holding her in my arms. I dream about being in bed with her, sleep tight, hol her. I also dream often about being naked in bed with her, my body against hers, full contact. I dream about this and I get wet in two seconds.

But there’s also that deep, deep love and affection. And I know that it is reciprocal. The other day, we ate at a restaurant. Her eyes lingered on me, just like mine did. But is it jist admiration, deep friendship? Then we said godd bye. We’re both leaving this summer. We walked to the station and I know those wereour last minutes together and I felt sad and tense. How would we say good bye? I turned around and said “We’re going to say goddbye, uh?” and she was behind me, looking suddenly sad, in a cute way, and said “we’re not going to see each other for two months!” and I thought how cute. We stopped at the entrance where we had to split. She said good bye, leaned toward me, an arm forward, and I just fell in her arms and hugged her. Not to tight, I was too shy. We stayed like this for a few seconds, and I stroke her back. I could tell she was happy, like she was hoping this would happen. Since then, we talked on the phone several time to “say good bye”. And now she’s gone, so that had to stop for good.

I can’t help thinking there’s some special connection bewteen us. It doesn’t matter if it doesn’t lead to a real lesbian relationship. If it is a very intense friendship with some physical love somehow, that’ll do for me. I just hope to be able to really hold her tight in my arms once, and tell her I love her. 

After you’ve got green lights from your desired woman, it is time to move from subtle lesbian flirting to major lesbian flirting.

Subtle lesbian flirting was explored in Smooth Flirting Moves of a Lesbian Temptress (1).

Of course, it isn’t a fixed rule that one needs to move from being subtle to obvious when it comes to flirting. Subtlety, however, plants you like a seed into her mind. If she allows it to grow into a plant with flowers blooming of fantasies, she may even make her advances before you do!

Major Lesbian Flirting

Invite her to your place.

Give her a very valid reason why she must turn up for the invitation.

For e.g. “ I dreamt of you last night. If you want to know what happened during my dream, you have to come to my place for dinner on Saturday.”

If she agrees to your invitation, she is ready for your advances.

Pick her up from work.

Walk close to her. If you are standing on her left and her left arm is behind her back, gripping her bag that slings on her right, she is actually withholding the urge to either put her arm around your waist or hold your hand.

What do you do? Walk even closer to her.

When you are having dinner, pick up some food for her with your chopsticks. It is a simple act that carries a symbolic meaning, especially to Chinese. One only picks up food for someone he/she cares about.

Sit close to her. Lean closer.

Tell her that the first time you saw her, you had already wanted to kiss her.

If she kisses you and pulls back, tell her you both better get back to eating, if not you’re going to lose control. Anyhow you both know what is going to happen later, better to eat your fill first.

Get really close to her and gently brush her hair back a little. Whisper softly into her ear. It is going to turn her switch ON.

After all that the following is usually inevitable.

 Image Source: Butterfly / Hu Die  

You tempt her. 

Do it subtly first, gradually turning up the heat 

Compliment her positive traits:

E.g. tell her how gentle she is. Say it with your gentle voice and gentle eyes.

Where she is able to see it from her sitting position, give her full view of one side of your exposed neck by turning your head. You have plenty of chances to do this when you are in a restaurant trying to look out for the waiter/waitress.

A lot of people don’t realise this; but the neck is actually quite a tempting piece of skin to bare.

If she gawks at your neck like that, you can turn up the heat by a notch. 

    When eating with her always watch out for any food around her mouth.

This is an excellent opportunity to help her wipe it off with either your fingers or napkin.

I would recommend the napkin though because many girls are very particular about anybody’s fingers touching their faces.

Although it does feel very sexy to have the corner of one’s lips lightly traced by another girl’s fingers, its better not to run the risk of her spending the rest of the evening worrying about potential breakouts on her face.

Also, when wiping her mouth with the napkin, do it gently and perhaps slowly, if not its not going to seduce anyone.      

Every time she talks about something that she gets emotional about, whether it’s something exciting or tear jerking, grasp her hands. It will make her feel like you want to share her emotions.  

You get the green light on grasping her hands when you find her doing that in return and she holds your hands a little longer than usual. 

Touch her on her arm whenever you want to tell her something and always maintain eye contact when you do this. 

Give her an innocent goodbye kiss on the cheek. It has to be the light and lingering kind.

Make her skin tingle and make the kiss linger in her mind.

This would be considered just a little more suggestive in the Asian context as giving goodbye kisses are not commonly practised among Asian women. 

It is important to look out for green lights and red lights during your subtle albeit seductive interaction with her. If you spot many red lights and she looks like she is going through trauma, do respect her space. If you spot green lights, you can graduate from subtle to not-so-subtle.

Moving on to more  smooth lesbian flirting moves  

Image Source: Butterfly / Hu Die 

What happens when you like an older woman who is shy and doesn’t exactly give out strong enough lesbian flirting signs for you to detect?

Look out for subtle signs that she likes you:

She fondles with her fingers a lot when she sees you. Coupled with a coy expression like that, she really DOES like you.

She cares about how she appears in front of you.

She flicks her hair away from her face when she sees you,

and has a tendency to stroke her hair like how a girl would, when she gently washes her hair by the river. It’s a very feminine act.

 Another give-away sign is when she keeps stroking her knuckles upon your arrival.

 And of course, she looks really shy when you are close to her.

If you like a woman who is really that shy, and she shows signs of liking you, do make the first move. Because all the moves she makes are probably only contained in her fantasies.

 Image Source: Butterfly / Hu Die 

If you are wanting to flirt with an older lesbian but you are not sure how to do it, take some cues from Annabelle in Loving Annabelle. Make sure you’re not legally underage though.

You know you like her when you do all sorts of things with your lips when you see her or think of her. 

You bite your lips.

You also touch your lips a lot because you wonder how it feels like if she is touching your lips like that.

You find yourself checking her butt out when she walks past you. She probably knows it because women have invisible eyes on their back. They can feel your gaze even when you are looking at them on the spy.

How do you flirt with her without saying a word? Give her the sideway glance with your subtle smile. If you can do it well its quite a come-on.

Send her flowers when she least expects it. Accompanied with an anonymous message you both have a mutual connection on.

See if she instinctively guesses its you.

Appear at her doorstep uninvited, wearing your sweetest smile so its virtually impossible to turn you away.

Whenever there is an opportunity to sit with her, jump on it. 

Inch closer to her and watch how she reacts. 

If you find her:

 (1) fondling her necklace,  

 (2) looking into your eyes intensely even in such close range,

 (3) glancing at your chest,

she could be attracted to you. 

If at the same time, she has created an arm barrier between you and her, she is also feeling a little defensive and is protecting herself from you.

Ask to take a look at her necklace so that you have permission to enter her personal space and she can’t put up her arm barrier. However if she places her palms together, she is still feeling defensive and closing her body to you.

If you’re bold enough, take your chance to trace her chest area around her necklace.  

When she gives you mixed signals of attraction and defensiveness, it might not be a good time to attempt to kiss her as you face a rejection possibility.

If you do face a rejection, back off gracefully and give her space.

As long as she doesn’t push you away and/or jump off the couch, don’t be afraid to interact with her again.

When you see her again, don’t be afraid to look at her like how you used to. 

Ask her out to a place with a relaxed setting. Get to know her and get her to know you. Whenever there is a chance, smile at her and engage her with your eyes.

Inch closer to her whenever there is space between both of you, close enough for you to smell her hair.

Touch her on the wrist. 

And perhaps, like Annabelle’s love interest, after all that flirting, she can’t help herself but finally surrenders herself to you.

Image Source: Loving Annabelle 

Older-younger or Age gap relationships have always appealed to many. The appeal is almost timeless, from Mrs Robinson to Loving Annabelle. In fact, it is regardless of orientation, gender, race or any other factors you can think of.

But of course, over here the spotlight will be shining on older-younger lesbian relationships.

Something Sexy : The Older-Younger Combination

There is just something incredibly romantic and sexy about being in a older-younger lesbian relationship, especially if both of you are at different stages of your lives.

E.g. She is the successful career woman sought after by the industry, while you’re the young and upcoming newbie under her mentorship; you’re the charismatic female lecturer, while she is your intelligent, earnest student…you get the idea.

Its as if you come from 2 different worlds, and struck by a specially formulated arrow drawn from Cupid’s bow, two magically becomes one.

I have always been fascinated with women older than me.

When I was a teenager I tried dating women in their mid-twenties to early thirties. Now that I’m in my twenties, the range got extended to dating women from the mid-twenties to early forties.

I used to think that the chances of finding a good bed partner was higher in an attractive older woman than the hot girl sitting next to you in lecture hall.

I was mostly right about my pre-conceived beliefs for my own experiences.

If this were to be plotted on a graph, it would depict an upward trend to a certain extent:

The older the woman I slept with, the more fun we had in bed.

But of course, that’s not the only thing that makes them attractive. (Although its an undeniably big draw)

Given their archive of social experience, older women generally exude more confidence and carry themselves pretty well.

Dating them, to me, is a whole lot of fun and the emotional connection is often refreshing. 

I like the conversations we have; the places we go; the food we eat; our different perspectives on the same things.

Older-Younger Lesbian Seductions

I especially like the way they drop subtle seductive hints when they find themselves liking you, before they say out loud that they like you.

I find their hints juicier than their verbal declarations.

Like for example, there was this one time, I met up with this lady whom I got to know from a party.

She was 39 and I was 22.

We met up for some coffee in the afternoon at a place that had cosy couches.

It was all polite at first, but as minutes passed, we found ourselves opening up and inching towards each other.

She was attractive and well maintained for her age, and looked like she was only in her late twenties, so I couldn’t help looking at her face a little longer than I normally would.

It was electrifying how she reciprocated the ‘looks’ and periodically broke into seductive laughter.

I was hooked.

Sugar & Spice : All Things Nice

If you’re a girl wanting to date an older woman, you probably wonder what will you have to offer to the relationship?

If an older woman is sugar, then a younger woman is all spice.

Younger women, with their hunger for new experiences, youthful energy and spontaneity, are infectious.

Also, the sweet adoration one gets from her younger counterpart is priceless.

An additional ‘perk’ you get when you have a younger girlfriend is that she keeps you more current than your peers and ‘extends’ your prime.

Plus you get a combination of sugar and spice in bed

Age gap: Is it a relationship issue?

Some of you might have heard some lesbian horror stories of manipulation: younger girlfriend­­s being presented as ‘trophies’, older girlfriends being exploited as ’sugar mummies’; but there will always be ladies like that around

You can be of the same age as your girlfriend; be manipulated in the relationship, presented as a trophy and treated like a sugar mummy. At the end of the day you have to be selective about who you date.

Can a older-younger lesbian relationship go the distance? I think it can.

Although there can be many differences in this relationship (just like any other similar age relationship), once you can connect and find what makes both of you tick, the differences you have becomes like the faded background.

Afterall, we’ve seen so many of our straight counterparts in age gap relationships living their happily-ever-after stories. So, why not us?