First Lesbian Experience
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First Lesbian Experience
DEAR DEIDRE Every night, I have to listen to my ex have sex with my housemate
DEIDRE'S STORIES Wes considers telling his best friend Amber how he really feels
I'M LONELY I feel so lost and aimless 15 years after affair led to divorce
AGAINST HIS WISHES Pal's daughter is selling off his possessions and putting him in care
DEAR DEIDRE: I’M having a lesbian affair with my mother-in-law, and I am terrified my husband will find out.
Last year, he and I moved in with his parents so we’d be in a bubble for lockdown and they could help with the kids.
Most people moan or joke about their mother-in-law but I’ve always got on really well with mine.
She has a great sense of humour, is kind and looks great for 53.
She had my husband very young — he’s 35 and I’m 40.
She and my father-in-law have had a rocky marriage for years, and just before Christmas they split up, and he moved out.
One night, my husband was at work and the kids were in bed when she suggested we have a drink together and watch a film.
I noticed she was really dolled up and looked beautiful.
In the middle of the film she started crying and confessed she’s a lesbian — that was why her marriage had ended. I comforted and cuddled her, and then she kissed me.
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It felt strange, but really nice, so I kissed her back. She led me up to her bedroom and I didn’t protest. I’ve never had sex with a woman before but it was amazing and so intense.
Since then, we’ve kept on doing it whenever we can. As soon as my husband leaves the room, we have a kiss, and sometimes I’ll sneak into her bed when he’s sleeping.
One night, I fell asleep in her arms. The only reason we didn’t get caught was because my husband had a lie-in.
My feelings for her are growing stronger and I’m sure my husband will notice the looks between us, or catch us in bed. I want to be with her but don’t want to hurt him.
My team and I are working safely from home but we are here to help you as always.
Every problem gets a personal reply, usually within 24 hours weekdays.
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DEIDRE SAYS: You know that if your husband finds out this will destroy not only your relationship with him, but his relationship with his mother – and your whole family.
He will be devastated that the two people he loves and trusts most in the world have let him down.
His mum may have turned to you for comfort, but encourage her to find support elsewhere and a relationship with somebody else.
Do you really think this relationship has a future? If not, maybe best stop now.
My support pack Can’t Be Faithful? may help to clarify things for you.
As for your marriage, are you still happy with your husband?
I’d advise you both to move back to your own home as soon as you can, and work on rebuilding your relationship.
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It was on a family trip to San Francisco , in my early tweens, that I saw what I recognized to be a real, true to life lesbian for the first time. Two, actually. I could tell because they held hands. After that, I started seeing lesbians everywhere. Well, not everywhere. But around. Whenever we left home, I saw women, often much older than me, loving other women: On the beach at the Mexican all-inclusive resorts my family vacationed at, walking down the same Main Street in a small Northeastern fishing town, at a second cousin’s wedding and reception in a midwestern town. Vacation, it seemed, was about lesbian-spotting. This was the early aughts, when absolutely no appropriate lesbian television shows or movies or really even books for girls my age existed.
My sixth sense continued as I grew up. I'd scout out lesbians, studying them as if looking for clues. My overactive imagination would wonder who these women were and where they lived and if their families still talked to them and if they had to lie at their jobs about their personal lives to afford a very nice vacation. I’d look at what books they’d leave on their pool chairs, what they ate and drank, and what they talked about, if I could hear. I was curious, totally unaware of why I was so staunchly fascinated by these strangers, like objects in a museum.
Years later, I found myself embodying my role as the lesbian at the resort with my now-wife, on a long weekend getaway to Sandals South Coast in Jamaica .
“Where’s Mr. Nice Guy?” our server asked us before we could decide if we wanted a lobster roll or fish sandwich and fries. I was confused, wondering if he meant the staff member who’d brought our bags to the room. “Where’s your man?” he asked again, insinuating that two very beautiful women couldn’t possibly be at a couple’s resort alone.
We hesitantly explained that we were together, and after a few seconds, the server fist bumped my wife, like I was an accomplishment, exclaiming something along the lines of “nice.” That became the familiar approval message once staff learned of our relationship status, though many seemed to completely misread why two women from New York were traveling together.
While our stay included a couples’ massage , staff insisted two women would prefer side-by-side facials instead. I don’t know if anyone suggesting this has ever had a facial, but having a stranger extract clogged goo from your pores anywhere near your partner is not my idea of romance.
Sandals resorts banned same-sex couples in 1981 , in efforts to maintain the chain’s exclusive image, allegedly prevent debauchery (still happens between straight couples on vacation, just FYI) and you know, to discriminate. In August 2004, following over a decade of criticism and pushback, the chain rolled back its restrictions, pushing for more inclusive marketing. It worked, swaying a proud, coupled lesbian like me to want to lay on the white beach and eat pasta chased by a frozen Bob Marley—three layers of slushie in the color of the Jamaican flag, thinned with a generous pour of rum.
A romantic setting at the Sandals South Coast
I generally don’t travel where I’m not wanted, preferring to support LGBTQ+ businesses in LGBTQ+ affirming destinations, but I’d actually been blissfully unaware of Sandals homophobic past. We’d stayed at one similar all-inclusive previously, an adults-only resort in Punta Cana we’d picked based off colorful pictures on a travel deal site. We didn’t really consider LGBTQ+ inclusion when picking that hotel. Sandals, whose marketing is targeted toward heterosexual couples eager for a luxe romantic getaway to a white sand beach, merely blended in with me to the majority of mass marketing in America. Perhaps it’s worth pointing out that there are zero lesbian resorts in the Caribbean, or anywhere, and the few gay properties cater to men.
The difference between the adults-only (party with friends) resort in Punta Cana and the couples’ (romance) resort in Jamaica wasn’t obvious to me until I experienced it: Everything was tailored for a man and a woman. Two women together were presumed to be friends, guests at one of the many weddings taking place on the property. This, of course, was nothing new: we generally don’t make our status as a couple obvious unless our surroundings seem safe. I was in Jamaica to relax, not to feel like I was being scrutinized or morally evaluated for holding hands with my partner.
Anywhere we go, including New York, our home , if we’re not obviously engaged in some type of PDA, my identity, as a femme lesbian, is often erased. When I’m out of my comfort zone, I’m not hiding—but I’m hyper-aware of my safety and surroundings: A taxi driver when I’m traveling solo doesn’t need to know my sexuality or relationship status; strangers at a couple’s resort, where we’re staying to unwind, relax, and hopefully, let our guard down, had to be clued in, and, as the hospitality industry is seemingly learning to do, be accepting, make us feel welcome, regardless of who we are.
On our last night in Jamaica, a folded piece of paper slipped under our door indicated that we’d been booked for a couple’s massage at the spa, just after sunset. It was unclear if the spa had ever accommodated a same-sex couple for a massage before (and I hadn’t thought to ask), but the masseuses walked us through a so-called love ritual involving the swapping of melting body oil candles and ostensibly enjoyed the same experience as any other couple staying on site.
As we slipped back into our oversize robes, a staff member encouraged us to relax out on the spa’s lawn chairs. Under the stars and illuminated by the light of the spa, several dozen towels lay rolled and styled across the grass. At a closer glance, they spelled out I <3 U, the arrangement adorned with kissing swans and sparkling red cocktails. We took a picture, laughed, and sipped our sugary drinks at the welcome cliche of it all. We were seen—and hearted—for who we were, if only in fluffy white hotel towels.
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No matter how much advice you received from friends, family and school, no one can ever really prepare you for that first break-up, how to go about your first kiss or what on earth to do when womanhood approaches you in the form of blood flowing from your nether regions. Our pubescent years are filled with tackling these ground-breaking life events in our very different ways, some of which we don’t always find comfortable to talk about. I sat down with a plethora of ladies and questioned them on just a few of the highs and lows of ‘femaleness’ and their experiences.
‘I did kiss someone when I was 3 but I don’t think that counts (it was magical). It happened again when I was 13 with a disgusting boy at a party, it was like a washing machine and then I was gone with the wind (again, magical).’
‘When I was 18, at a house party. He asked me if I’d like to go out for some air. At this point, I had no idea what going out for air meant. He just pushed his face into mine and frankly, it was awful. But he’s now gay so I feel like it’s all worked out for the best.’
‘He was my boyfriend in year 9. We’d been out in the park, he walked me home and we kissed on my front door step. Worst moment of my life, and I don’t think I kissed another boy for a year.’
‘I was 13 and it was on Wandsworth Common where everyone used to go and just get really drunk. Some creepy guy dragged me off and I swear, his tongue explored my face in its entirety. S C A R R E D.’
‘I was 12, nearly 13 and it just happened in John Lewis. Very middle class.’
‘We were on a family holiday in the summer after Year 8. One day, I had a massive argument with my mum because she didn’t like me buying boys’ clothes. That same day, I just started bleeding. Cried on the bathroom floor for hours. The sheer irony of that day still gets me.’
‘I was 11 and I didn’t know what a period was. I cried because I thought I was dying and then thought I was pregnant. Cried to my mum and told her what happened. She hugged me, congratulated me on being a woman and then promptly called all the females in my family. When I came home from school that day, my brother had found out and was discovered sat on the bathroom floor crying whilst looking at pictures of me as a small child.’
‘I got mine when I was 8 or 9 and told my mum who then slapped me across the face. Apparently it’s tradition.’
‘Mine was in year 7. I remember I was in History and needed to go to the toilet. When I got up, I accidentally flashed all my friends but didn’t really think anything of it. It was when I got to the toilet that I realised I had started my period. Half my class had seen my bloody knickers.’
First time you shaved or waxed your lady-garden?
‘I think I was going to a party when I was like 15 and some people were allowed to stay over. I’m not sure what I thought would happen but I wanted to be prepared at all costs, so I stole my mum’s blunt razor and got to work. It was a real hack job. I then stayed away from boys at all costs, no one needed to see that.’
‘Don’t remember when it actually happened but girls started talking about it so I went home and gave shaving a try. Probably for the best because I got fingered a week later.’
‘I actually went for the scissors first. I wasn’t really looking and cut myself a few times which fucking hurt. Then I found my dad’s razor and ended up with a terrible shaving rash and war wounds.’
‘I was 14 or 15. I had a free house, and this guy came round. We were getting drunk and getting off with one another. Things started getting hot and heavy so I told him that I needed the toilet and I locked myself in and shaved literally everything including my forearms.’
‘I remember my first time because I was in the bath and the shower head ended up between my legs and was feeling quite nice. Got quite into it and then the shower head came off.’
‘I was pretty young, between 10 and 12, and I didn’t know what I was doing. It involved a pillow. I was basically dry-humping a pillow. My mum walked in. It was under covers but she knew. She. Knew.’
‘I think I was 15 and this girl had sent a video of herself masturbating to a boy, who in turn ended up sharing it with everyone. Me and my group of friends were like, “well, gonna give this a go and see what all the fuss is it about”.’
‘It was a very long time ago and I thought it was the most incredible thing in the history of the world and thought no one else could do it, almost like a secret power. Used to do it all the time and then slowed it down, because it was getting weird.’
First time you did anything sexual with a boy
‘I was 16 with a long term boyfriend. He fingered me and that was it. It was pretty good, I can’t really remember it if I’m being honest, all I know is I didn’t want to touch his penis.’
‘Everything happened on the same night. It was so painful, we just went from one thing to another. Finger, penis, done, ouch. He got a condom from his parents’ room which I realise now is really weird. I was in so much pain afterwards and then ran to the toilet and cried. Then he bought me Ben and Jerry’s which we ate in bed. Cute.’
‘Kinda half gave someone a hand-job in an ICT lesson. Classic.’
‘It was on a beanbag in my mate’s house and it was weird because my hand was down his trousers, holding his penis but I didn’t know what to do with it. You know at primary school when you’d have to put your hand in a bag and try to figure out what was in your hand? It was like that. Like a blind man trying to peel a carrot.’
‘After 3 attempts of trying and failed miserably to have sex, we gave it another go. We were passionately kissing, clothes were off, he was on top and then next thing you know, he whispered in my ear that it was in. To which I responded ‘really?’ Afterwards, I sang ‘Like a Virgin’ by Madonna.’
‘It was actually not bad, it obviously hurt a bit. Bled a bit but not a lot because I dance. The next day when I was getting the train from his back to mine, I remember being at the train station and feeling really aware that everyone knew what I had done.’
‘I’d had sexual relations with a boy about 5 minutes beforehand, and being the horny hunni that I am, another guy who was interested started getting off with me and we were just canoodling in a dark room. Another friend entered the room and unsuspectedly started chatting to us about X Factor. It was simply not the time nor the place so we decided to move the party to the downstairs bathroom and my first real sexual position was standing up doggy style. When it was over, I went home and cried a bit because I was really hungover.’
‘It was with my boyfriend in year 11 who I’d been together with for 8 months. I invited him round thinking that it would be the day it finally happened. We had one condom. He got really nervous and ripped it. It was not the day.’
‘It was devastating. We had an intense summer romance over 4 months. One night at Crisis I got a text from him out of the blue saying ‘I don’t think this is going to work anymore’. I didn’t speak for 5 or 6 days afterwards. He told me I had to get over it and when I stalked him on Facebook, I discovered he had gotten a girlfriend. Since then, I’ve never actually fallen for someone else.’
‘It was primary school. He was actually quite a rebel and I was attracted to the bad boy in him. I think I thought I could change him, We’d double-date with another couple and all go to the playground. But then it just fizzled out.’
‘I went to a house party. I was just not feeling the relationship anymore and he kind of brought it up whilst we were sitting with his friends. We ended up breaking u
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