Sindhu Vee

Comedian

I lost my virginity late, in my early 20s. I was born and raised in India, which was very conservative, and I wasn’t going to do anything that my mother would kill me for. But maybe the bigger reason was that no boys liked me. By Indian standards I wasn’t attractive at all: I was too tall, dark skinned and very academic – a monster geek.

Sindhu Vee: ‘My entire aim on getting to university was to meet a boy and have sex.’

When I got a scholarship to study at Oxford University, aged 21, my entire aim was to meet a boy and have sex, which is crazy. Everyone kept telling me I wasn’t giving off the right signals, but I was literally asking boys: “Would you like to sleep with me?” People must have assumed I was on drugs.

Eventually I was introduced to someone wonderful and we began dating. There was a lot of romancing, and after a couple of months it finally happened in my dorm room. There had been such a buildup of sexual energy, and we really liked each other, so there was a lot of trust and no awkwardness. All the emotional groundwork was there for us to have a great time.

I woke up the next morning and said, “OK, so now we’re getting married,” which scared the shit out of him. Then I ran to the payphone in the hallway and called a cousin in India and one in Mauritius and shouted down the phone, “I did it! I did it and it was amazing!” Everyone could hear – he must have been mortified.

We were together for six months before I moved to Canada to continue my studies, and we couldn’t make it work long distance. I was heartbroken – but after a while it felt like I’d come back from the dead. I felt very empowered because I’d survived this tsunami of sadness, and now I was free. For so long I’d felt like an unattractive weirdo, but now I was like everybody else. I’d had sex!

Sindhu Vee’s Sandhog second leg UK tour runs from 5 September to 14 November. www.sindhuvee.com

Alix Fox

Broadcaster

I relinquished my virginity aged 16, atop a truly repulsive sofabed. It was a pull-out affair (the settee, not the sex), covered in an awful fluorescent fabric, which was more painful than the penetration itself. Mum happened to flog it not long afterwards, and I remember feeling a mix of amusement and nostalgia as a stranger hefted the satsuma-hued site of my deflowering away in a Ford Transit.

Alix Fox: ‘It was precious and gentle and sweet; I was on top – of him, and the world.’

I’d decided to sleep with my rugby captain boyfriend as the ultimate keepsake for him to take on tour. However, on the designated night, he arrived white-faced, straight from having witnessed a particularly gruesome scrotum injury on the pitch. Thankfully, the deed itself made up for what preceded it. It was precious and gentle and sweet; I was on top – of him, and the world.

Other aspects of my life at that stage were, to put it mildly, a rough ride. Many of the messages I was receiving at that time about men and relationships were steeped in fear, oppression and violation; against this backdrop, it seems an even greater blessing that my first formative foray into sex was so positive and pure.

I know how rare it is for “losing it” to be a winning experience. Every week on my radio show young people share stories of sexual misadventure with me, from the cartoonishly hilarious – like the girl who masturbated with a frozen sausage so cold it adhered to the walls of her vagina, and whose doctor father instructed her to melt it out in a warm bath, mere weeks after he’d retrieved a deodorant can lid from the same orifice – to the crushingly heartbreaking. I was so lucky. Losing my V was a victory in proving to me that sex can be a loving and lovely thing.

Alix Fox co-hosts BBC Radio 1’s Unexpected Fluids podcast, sharing “real life tales of sexual fails”, and presents the Guardian’s Close Encounters audio documentary series

Dan Savage

Author and advice columnist

My first time was a clarifying experience. I was 15 and it was a three-way with my older brother’s twentysomething ex-girlfriend and another guy.

Dan Savage: ‘I really wanted to sleep with him, not her, but couldn’t admit that.’

Strategically, it was a good move because I wasn’t ready to come out to my family, and this gave me a little bit of plausible deniability. I made sure everyone at home found out about it, including my brother, and it bought me some time.

The three of us were hanging out at a camping trip for cosplayers. They were both sexually adventurous, and I think she enjoyed the naughtiness of seducing her ex-boyfriend’s younger brother. I really wanted to sleep with him, not her, but couldn’t admit that – and I was really worried that if he caught me looking at him he’d realise I was gay and kill me, which was a little stressful. The other guy went first, and I was having a hard time finishing. Then he reached between my legs and cupped my balls to help me, and boy did it help!

I dated the girl for the summer, and we even had a pregnancy scare, which made me realise that imagining Shaun Cassidy wasn’t effective birth control. Looking back, I’m grateful to her, because she gave me a gift. I wanted to have sex with a woman to prove that I could, but in the end I realised that I couldn’t. What I was doing wasn’t kind to a person who was being kind to me. It was an experience that really helped me understand myself.

Dan Savage is the host of www.savagelovecast.com

Russell Kane

Comedian

The first person I kissed was the first person I slept with. Until I was 16 and a half, there was no indication that I’d ever touch a woman. Then I crashed another school’s prom, and was told that there was a blonde girl who liked me. At first I thought there’d been an administrative error, but then we snogged and I fell immediately in love.

Russell Kane: ‘I was told that there was a blonde girl who liked me. I thought there’d been an administrative error.’

About three weeks later, we started stumbling towards losing our virginities. I’d had years of practice of self-love, but she’d never given herself an orgasm. I couldn’t enjoy it unless she did, so – unusually for a teenage boy – I struggled to orgasm the first few times. We were both learning at the same time.

We dated until I was 19, and when she ended it I was absolutely crushed. I can still see my snot and tears on her shoes as I got down on my hands and knees, begging her to take me back.

That first relationship established a pattern of serial monogamy, where if someone touched my shoulder I’d fall in love with them for three years until they dumped me. Sex and love were completely joined for me, which wasn’t always that healthy. Once I had a profile and was getting female attention, I wished I’d had more one-night stands when I was younger, so I gave myself a year of being single and enjoying that sexual freedom. It only took five months for it to start feeling hollow, and then I met my wife. Now I’m happily married with a baby, so I’m glad I finally got it out of my system.

Russell Kane tours the UK with The Fast and the Curious until December 2019: www.russellkane.co.uk

Desiree Burch

Presenter and comedian

I was a virgin for a long time, until I was 22. I could blame it on my Christian upbringing, but it had more to do with my low self-confidence as a fat, nerdy kid. By a certain point, having my virginity no longer felt cute – I needed to get rid of that fucker!

Desiree Burch: ‘We’d gone out to see the movie Secretary, so we were both hot for it.’

In the end, I lost my virginity twice. The first time was easy; it was with a friend of a friend. We were at a party and she took the initiative. I was surprised by how into it she was, because I’d never thought of myself as the one who would be pursued. We had a good time and I got off – but I still thought I needed to do it with a boy for it to count, which is messed up. Internally, something had shifted and I was more of a sexually actualised being, who took more joy and pleasure in my body. But I still had this notion that I needed to do it with a man to make it “official”.

The first guy I slept with was a very nice comic book nerd who I met on OK Cupid a year later. We’d gone out to see the movie Secretary, so we were both hot for it. He knew I’d never been with a man before, but he’d been with women already, so at least one of us knew roughly what we were doing. It wasn’t the best sex ever, the first time never is, but I still skipped my whole “walk of shame” home.

I felt like I had crossed over a threshold into the grownup world. We didn’t see each other again, but I felt released from the burden of my virginity.

I’m glad I waited until my 20s, because I was emotionally all over the place in my teens. Maybe if I’d lost my virginity at university then I’d have saved myself a lot of time feeling anxious about it. Then again, I went to university with a lot of weirdos, so maybe it was better for it to happen in real life with normal people.

Desiree Burch presents Flinch with Lloyd Griffith and Seann Walsh, available now on Netflix.

Matthew Todd

Author and former editor of Attitude magazine

I was 17 and my first boyfriend, Sam, was six years older than me. It was 1991; the age of consent for gay men was 21. We were both in the closet and living at home, so even kissing in his car, terrified every time a police car went by, was planned like a military operation. It’s not like two young gay guys could sit necking at a bus stop then (or now).

Matthew Todd: ‘For my straight friends, the thought of sex was sanctioned and tacitly celebrated.’ Photograph: Linda Nylind/Guardian

For my straight friends, the thought of sex was sanctioned and tacitly celebrated. Sex education warned them they could create a new life and me that I could end mine. So when Sam and I did sleep together it was an intense moment.

We knew we’d have an opportunity when his parents went away. He told his sister I was a friend who was staying the night, in his room, on the floor. It was like trying to have sex next to an unexploded bomb. If his sister had come in then we’d have both been in serious trouble. I could recount to you tales of fireworks and shaking headboards but it wasn’t like that. There was just a relief of being able to be physically close with someone I cared about. I remember him grinning a lot the next day.

We dated for nine months and didn’t sleep together many times because we couldn’t, which contributed to the split. When we did, though, it was always more about the closeness. He was (and is) a decent man. I am grateful that first time was gentle, loving and something I don’t regret.

Matthew Todd is the author of Straight Jacket (Black Swan) and Pride: The Story of the LGBTQ Equality Movement, published now by Carlton Books