When Kate Monro decided the moment had come to lose her virginity, everything seemed to fall into place perfectly. She was 15 and on holiday without her parents for the first time. Every night she and her friends would hit the dance floors of the Costa Brava. "We would spend all night in proper 1980s discos, drinking piña coladas and being chatted up by hairy Spaniards who looked like members of Wham!" she says.

One night Monro got lucky. In walked an exquisitely good-looking French boy – a whole year older than herself and so sophisticated he was holidaying alone. "I was enthralled," she says, "like a moth to a flame. I figured out pretty quickly this was my big opportunity to lose my virginity." The pair planned it carefully and on the last night of the holiday he took her up into the hills where they found just the right spot by a swimming pool overlooking the sea.

But in the event, Monro's French Adonis turned out to be a bit of a letdown. It was mechanical, boring and uncomfortable. "My absolute first thought was: Oh, this feels like three Tampax instead of one," she says. "Nothing more." Even so, when it was over, as it was in a flash, Monro skipped back down the hillside feeling euphoric. "Losing my virginity was absolutely top of my list of things to do," she says. "I felt stigmatised by it. I always thought I was such a maverick with my dyed hair and ripped jeans, but my friends had done it, therefore I wanted to do it, too."

Despite her own lacklustre experience, virginity loss is a subject Monro, now 42, has become deeply intrigued by. For the past five years she has scoured the world, collecting tales of first-time fumblings through her blog the Virginity Project. She has now amassed hundreds of stories which she plans to turn into a book.

Monro believes sharing your virginity loss story is one of the most exposing things you can do, and all her case studies remain anonymous. "It's one of the most vulnerable moments of your life," she says. "Nothing can ever prepare you for the reality of it. It is you at your most unknowing and innocent stepping into the sexual arena for the very first time."

One of Monro's subjects is Betty. She lost her virginity on her wedding night in 1940. "I never knew what a man even looked like until I got married," she told Monro. "Sex was a forbidden subject. I was frightened, and when I saw how he looked I laughed." And more recently there's the 16-year-old whose older brother treated him to a Mancunian prostitute. "Thoughts swirled in my head," said the boy. "Don't come too soon. Is £35 a fair price? What do they do in porn?"

Monro seems to have an ability to get people to open up to her and there are many who tell her things they can't even tell their own partner. One of the most candid stories on her blog is the tale of the stay-at-home father of four whose wife, a high-flying lawyer, decided one night to strap on a dildo and take his anal virginity. "I was, to put it mildly, petrified," he says. "The sight of that missile protruding from her, and meant for me, brought everything home."

She also has tales we wouldn't usually hear: of a thalidomide boy (lost his to the most popular girl in school, then moved on to her best friend); an autistic man (prostitute) and a 101-year-old woman (out of wedlock, scandalous, but a bit hazy). But the story, she says, that always shocks the most, is that of the man who has been married for 15 years yet is still a virgin. "He had the opportunity to do it but just had an intense feeling he would hurt the woman and couldn't do it," she says. "I think it has just turned into phobia."

In many ways Monro's work is a valuable snapshot of sexual mores from the past 60 years. Betty, for example, is a product of a time when virginity loss and marriage went hand in hand. For Monro, meanwhile – a child of the 1980s, in those heady days post-pill, pre-Aids – it's little wonder she behaved the way she did. And these days? According to the latest National Survey of Sexual Attitudes and Lifestyles (Natsal), which studied more than 11,000 people aged between 16 and 19, the median age of virginity loss is 16. Interestingly, ever since the mid-1990s the proportion of women who lost their virginity before the age of 16 suddenly stopped increasing and along with that use of contraception went right up, too. Could it be that some messages are filtering through and we, as a nation, are becoming more and more sensible?

On her blog Monro cites the work of Laura Carpenter, professor of sociology at Vanderbilt University in Nashville. Carpenter did a scientific study of 61 people and, in the resulting book Virginity Loss: an Intimate Portrait of our First Sexual Experiences, identifies three distinct categories. First there are the "gifters" – "People who see virginity as a precious thing and who want to find the perfect person to give it to," explains Carpenter. The second are the "stigmatised" – the group to which Monro clearly belongs – and finally there are the "processors" who see virginity loss as just one sexual experience in many, a category which, Carpenter found, many gay and lesbian people fell into.

"One of the things that struck me was that men and women were far more similar than we would expect," says Carpenter. "When you find women who talk about virginity as a stigma, the choices they make are really very similar to men – they don't care who they do it with, they just want it over with. While the men who saw virginity as a gift were very like women gifters – concerned about finding someone special to give it to."

American filmmaker Therese Shechter started out as a gifter. "I was waiting for that special person," she says. "I really felt I had this thing that I wanted to bestow on the right person." By the time she hit 23, however, she was the only virgin left in her peer group. "I eventually realised this special person was not coming, so I needed to do it with someone unspecial. When I did my first thought was: 'Great, it's done' – my second: 'And this was what I had been saving myself for?'"

Shechter, who directed the award-winning 2005 documentary I Was a Teenage Feminist, is now working on a follow-up called How to Lose Your Virginity, which is due to open in America in the autumn. She was inspired to make a film about virginity partly by her horror at the rise of the abstinence movement in America and partly by the experience of planning her own wedding. "I realised it was a similar ritual to a purity ball – the process of handing your virginity from your father to your new husband," she says. "For me that was something pretty ugly and ancient."

Like Monro's work, Shechter's film is a series of straightforward tales of real people's virginity loss. It's refreshing to hear such forthright voices in a world where any debate about virginity is often so conflicting or one-sided. Our current torchbearer seems to be Miley Cyrus who, just like Britney all those years ago, loudly proclaims her own virginity while behaving in a hyper-sexual way. In the media there are constant stories about women auctioning off their virginity to pay for their education and more troubling is recent news of one Justin Sisely, an Australian TV producer currently looking for young virgins to take part in a new reality show. "You see all this stuff and you think: 'So this is the extent of the debate we're having about virginity in the 21st century?'" says Shechter.

It's a sentiment Monro agrees with. "These days we see sex everywhere, but there's very little that's honest about it," she says. "I think ultimately what brings people to tell me their stories is that we all have an innate desire to want to compare our experiences with other people. We all just want some sort of affirmation to know that we are normal."

virginityproject.typepad.com

Donnie, 31, lost his virginity in 1998



I was in college, working at a bookstore. I had a key and often worked late at night and this meant that I and the girl I loved had a place where we could go and be away from our roommates. To say that I loved her would be a pale word. I savoured her. Every angle, every facet of her mind and her words and her eyes seemed to infuse me with an energy that I had never experienced before.

One night, late in the dark store, after talking about Joseph Conrad novels, we kissed more and more deeply, and everything began to spin around me; all the square angles of the books and shelves blurred like a cartoon as I removed the lace from the curves of her body. We were laying on the floor between shelves of old books. I remember how her heat surprised me. I remember how her legs felt when they moved up around my ribs. I remember something she whispered to me — a whisper I sometimes still hear at night. I remember playing with her hair afterwards, as we lay together panting and hot. And most of all I remember the feeling much later, as the sun was rising and we left the store. She was wearing my coat. And everything in the world was different. I noticed it instantly — as though everyone had been speaking in a foreign accent and now suddenly switched to my own.

Arthur Perks, 86, lost his virginity in 1943



I had no idea at all about sex. I never even saw my mum and dad kiss each other. I did think of going to a prostitute to show me how to do it, before I made a fool of myself, but I didn't have the courage.

In 1942, when I was 22, I joined the army so I never had time to go with women because I was a front line soldier. Then we went into Austria and annexed a couple of hotels on a lake. It was beautiful and I used to row round the lake and one night, there was this girl standing on the jetty.

She took a fancy to me and I began to get a stir if you know what I mean. One night we had a nice night of rumpity-pump and it happened. Just like that. And the unfortunate part of it was, there was nothing splendid about it at all. I got the erection and bob's your uncle. Away we went. Of course we weren't so adventurous in those days. You didn't try positions or anything like that, women are more forward today than they ever were back then.

Mathilde, 20, lost her virginity in 2009



When I was 17 I was desperate to lose my virginity. I met him at midnight after a party and we planned to do the deed in someone else's bed. I saw him as my golden ticket into the amazing world of sex. We started kissing. He was very heavy, we undressed and he pushed and it hurt like hell. He wanted to stop, but I told him to keep going. Eventually he got inside me and started thrusting. I remember that it felt crooked. Our friends called before he could finish and I don't think we ever really spoke again.

I was always afraid to have sex after that. I made out with guys naked on the kitchen table in the common kitchen. I gave blowjobs to more than I'd like to recall, but I couldn't do it. I couldn't have sex. I didn't get another boyfriend until I was 20. He was a virgin too and eager to do the deed. I told him I was a virgin, because in my mind I was.

Marcus, 32, lost his virginity in 2007



At 29, many years of falling confidence had taken their toll. I was at a nightclub with friends when a female friend who I had always thought was stunning but out of my league, drunkenly confessed that she really liked me. I was in total shock. Before I knew it, we were kissing and she made it clear that she was willing to have sex that night, but I felt wary of her being quite drunk that we left it at that. We met a few days later and hit it off right where we left off. Before I knew it we were on her bed, then becoming naked – a new first for me – and then we were doing all those things I was beginning to wonder if I was ever going to taste. And it all felt so natural. For a first time, I would guess it was pretty good. As we talked afterwards, I told her that that had been my first time, and she was shocked. She said she never would have guessed.

Paul Howden, 48, lost his virginity 1976



I was 15 and had been going out with this girl for a couple of months. I was going past her house in Edgware one day in the school holidays when suddenly a torrential rain storm came down.

I knocked on her door and my girlfriend's mum opened the door. She invited me in and told me to go into the living room and take my wet clothes off while she went off to get some towels. When she came back I was standing there in my underpants. She told me to take them off and then she started helping to dry me with the towels.

She started on my chest then did my back. She was kind of stroking me rather than drying me. Then she told me to turn round and she basically starting towelling me lower and lower until she was drying my bits and stroking them through the towel.

She got me aroused, which wasn't that difficult, and then told me to lie down on the carpet. She was wearing a lightweight summer dress which came off in seconds and she sat down on me. I remember feeling a combination of utter embarrassment, elation and fear that my girlfriend would walk through the door. I was also terrified of getting her pregnant. It was all over in a minute, if that. I vividly remember noticing lots of pictures of her daughter, my girlfriend, scattered round the room.

When it was over she got up and we sat there on opposite sofas waiting for my clothes to dry having tea and biscuits. I just wanted to get out of there. She told me to come back the next day to do it properly. At 15 you don't expect to be pounced on a by a woman in her 40s.

Juliette Robertson, 33, lost her virginity in 1994



I was 17 and a half and one of the last among my friends to lose my virginity. I'd been seeing this guy I'd met over the summer. He was three years older than me and had his own car and seemed a lot more grown up than me. From the off he wanted to have sex but I was totally nervous. In the end I made him wait four months as I wanted to feel like I had got to know him.

The night we planned to do it I told my mum that I was staying over at my friend's house. My boyfriend told me to dress up because he was taking me on a date. He arrived to pick me up in his car and revealed that he was taking me to the opera to see the Magic Flute. I was dressed up in a full length gown. I thought 'this is so grown up and romantic, it's going to be perfect, perfect.' It's hilarious when you think about it now.

I couldn't understand a word of the opera and all I could do was sit there thinking over and over again I'm going to lose my virginity tonight. Afterwards we went back to his. He had tried to create an atmosphere with candles, pink flowers and Pink Floyd playing on a loop. The whole thing must have been over in seconds. Weirdly, I don't really remember the details of the act itself, but I do remember having that classic feeling of is this really it? And brilliant, I've done it.

• This article was amended on 27 July 2010 to remove a first-person narrative.