First-Time Sex: How I Lost My Virginity
I have already written about two of my personal sex experiences on this blog, My First Anal Sex Experience and My First (Surprise) MFM Threesome, but not about a major milestone in every girl’s life, losing my virginity. It seems a long time ago now, but it’s not something you ever forget.
After Christmas break of my freshman year of high school, a senior boy asked me out. I’ll call him “Jason.” Jason was good-looking and popular, and being asked out by him was a major boost to my self-esteem. I was embarrassed by my Russian accent and still felt socially awkward and out of place. I even went by Lana back then, to seem more American.
Being asked out by a popular senior boy was also a boost in my status among my friends. They tried to get even by warning me that older boys expected sex from girls they dated.That did give me pause. I was no stranger to fooling around with boys, but my sexual boundaries didn’t extend that far. I had gone as far sexually as being felt up by a hand inside my panties, but up till then, only my bra had come off, never my panties. That would change soon.
Going out with Jason was everything I imagined it would be and everything my friends warned me about. He took me to a party at a senior cheerleader’s house. A lot of older boys and girls whom I’d seen around campus, but didn’t know, were there. Jason introduced me to all his friends and almost never left my side. Everyone, except for a few of the girls, was really nice to me. It was one of the most fun nights of my life.
That night also began Jason’s assault on my virginity. It started at the party when we kissed and he slid his hand inside my top, and continued at his house after the party. When we got there, the house was empty. It wasn’t long before Jason was pushing past all my previous sexual boundaries. Not only was my bra off, but so were my panties, and not only was there a hand between my legs, but Jason had stuck a finger inside me, too!
That kind of snapped me out of my sexual trance. I said I had to go home. Jason laughed and asked if it was past my bedtime. His insinuation stung, but I insisted my mother would kill me if I didn’t get home right away. “I thought you were cool,” he said. I promised that I’d make it up to him, but that my mother would ground me if I got home too late.
“At least jack me off,” he replied. “All girls do that.” I never had, but I thought I knew how. It turned out I was wrong. He kept telling me to do it harder and faster. Finally, he came – all over my hand. It was the first time I’d made a boy ejaculate (that I knew of). He took me home after that.
Jason didn’t call me the rest of the weekend. When I saw him at school, he was friendly, but a little distant, it seemed to me. I worried that he was going to dump me after one date! That wouldn’t do anything for my new-found status – or my self-esteem. Plus, I liked Jason and liked being with him. When he wasn’t trying to have sex with me, he was really fun to be with. Actually, his trying to have sex with me wasn’t bad, either. It was just such a big step to take that it scared me.
I decided that I needed to grow up. If Jason wanted to have sex with me, that was sort of a compliment really. He was the best boyfriend I’d had up to then, for looks and popularity. I was going to have sex eventually anyway. If Jason still wanted my virginity, he could have it.
I demonstrated my new maturity by hanging around Jason like a puppy dog as much as I could. I even went to his basketball game and cheered wildly for him every time he touched the ball. That must have given him the idea that I’d had a change of heart. He asked me after the game if I wanted to come over to his house and hang out. I said sure.
Jason hadn’t said that his parents weren’t home, but I wasn’t surprised to find that they weren’t when we got to his house. I had crossed the Rubicon. I wasn’t leaving there a virgin.
Just like after the party, it didn’t take long for us to be in his bedroom making out. I was soon completely naked with Jason down to his tighty whities, and just like before he had a finger inside me. This time it excited me instead of scaring me, though. I saw the bulge straining the front of his briefs and decided it was time.
I lay back on the bed and let my legs fall open. That was all the hint Jason needed that I was ready. He pulled off his briefs, got a condom out of his nightstand drawer, and put it on. That made me feel a lot better. I had thought about condoms, but where was I going to get a condom? It was a huge relief that Jason had one. Now I was really ready.
Jason climbed between my legs. “It’s my first time,” I said. “Don’t worry. I won’t hurt you,” he answered. That turned out to be a lie.
Jason positioned the head of his penis at my opening. I was practically shaking from fear and excitement. Then he pushed in. At first it wasn’t so bad, but when he pushed further inside, it started to hurt. It really hurt. It felt like he was pushing against something solid, like something was ripping inside of me. I must have winced or cried out, because he stopped and asked if I was all right. “It hurts a little,” I lied.. “I’ll go slow,” he promised.
I can still remember when it started feeling good. For what seemed like the longest time, I just lay there wanting it to be over, then it started feeling good, then it started feeling really good – and then it was over. Just as I was beginning to enjoy this amazing feeling, Jason thrust hard into me several times, lay still for a few moments, and then pulled out. It was definitely over, and so was my life as a virgin.
I went to school the next day, and I must have been wearing my I’m-not-a-virgin-anymore smile. My friends surrounded me and pumped me for all the details. Jason didn’t dump me after “popping my cherry,” either. We went out for the rest of the school year and all through the summer until he went away to college.
I experienced a lot of sexual firsts with Jason. Besides giving him my first hand job and my virginity, I also gave him my first blow jobs. Sex got better, too. I began having orgasms. Jason even went down on me. Losing my virginity to Jason really jump started my sexual life. I have a lot of sweet memories of our time together.
What was first-time sex like for you? Was it everything you expected it to be or a disappointment? Tell me about it the comments.
Similar Posts:
- My First Anal Sex Experience
- Strap-On Sex: The Politics of Penetration
- At What Age Celebrities Lost Their Virginity
- 4 Tips for Negotiating a One-Night Stand
- Virgin Swingers: Should We Have Sex with Our Friends?
Tags: first-time sex, losing virginity, personal sex experiences, virgin girls
I came to the U.S. at age of 12 with my mother. We settled in sunny Florida, which was quite a contrast to Minsk. I have always been fascinated by sex and relationships. My sexual history and preferences are detailed in my post 
January 7th, 2011 at 6:16 am
Several years ago I wrote a piece of erotica, which, though in the third person, describes exactly my own first time. I’m the “he” in the story.
“Will you come home with me this evening?” she asked. “After class?”
“Why?” Though he had wanted to be alone with her since the first time they had met, the offer had taken him by surprise. “Can I help you with something?”
“With my homework,” she said. “Of course not, you nut. I just want to have a drink with you.”
After the class was over (and he honestly did not hear a thing the teacher said all evening) he, accordingly, did not try and make his way to the bus stop. Instead, he walked over to the car park, as she said, not too close to her. No one seemed to notice. She was the most sought after girl in the class, but no one seemed to be after her this evening. Maybe it was just too windy and cold.
The Maruti was warm inside. Perhaps it was just the absence of the wind. She was already behind the wheel. Not knowing what to do, he sat as far away from her as possible.
“Come on,” she said. “Come sit a bit closer, not pressed against the door like that.” He moved towards her, gingerly. She had already driven out of the parking lot and in a minute they were driving down a road he had never been on before. Traffic was light and houses few.
“I live quite a way off,” she said conversationally. “It’s not that easy to find transport, so I do need this car.” After a pause, she added, “I bought a bottle of rum and cola. I need you to help me finish it.”
“Your parents won’t object?’
“They’re out of town for this week,” she said. “And they do give me my space.”
Her house was single storeyed, in its own small walled compound, with a tiny grassy lawn in front. The garage was next to the gate and she manoeuvred her car in while he opened the gate and the garage door. She entered the house directly from the garage, came to the front door, and let him in.
“It feels a bit odd to bring you in through the garage.” There was a smile in her voice. “It would be as though I were smuggling you in.”
She sat him down in the sitting room, with its slightly overstuffed chairs and its reproduction paintings on the walls. She disappeared for a moment and returned in a grey T shirt and old blue jeans. She still wore the ugly sandals she had worn all evening. “We won’t drink here,” she told him. “I’m just expecting a visitor. As soon as she’s gone we’ll go off to my room and drink there.”
The visitors – there were three of them, two girls and a long haired young man – turned up almost on cue. They were loud and giggly and spoke of people he did not know doing things he did not understand. It was almost like a code language. They did try to involve him in the conversation but obviously realised it meant nothing to him, and soon left.
“Sorry about that,” she said, locking the door firmly behind them. “I hope it wasn’t too boring for you. Let’s go over to my room.”
Her room had a poster on the door, “Abandon All Hope, Ye Who Enter.” It was large and roomy, with a double bed, wall wardrobe, a dressing table with a mirror and a large music system. At the back was a door opening to a bathroom.
“I’m sorry,” she said again, “but there’s no food in the house, just a couple of packets of chips.” She produced them, and the bottle of rum and cola, expertly opening the latter and pouring measures into two glasses.
“It doesn’t matter, really it doesn’t.” He was sitting where she had indicated, on the bed near the dressing table. She put a CD into the music system. Amplifiers, set on low volume, brought in the song from all sides. Roxette, Crash Boom Bang.
“Let’s sit on the floor,” she said, suiting herself to the purpose and patting the floor next to her. It was easy to slide himself down. Ample leg room to stretch his long legs in the available space.
The rum and cola mix was surprisingly good. He tried to go slowly, but suddenly found his glass empty. She was already on her second, and poured him another.
“I don’t normally invite boys home,” she said, putting her hand on his shoulder and her chin on the hand. “I don’t want you to think I’m doing something wrong.” It all suddenly seemed absurdly solemn, and he fought down a desire to laugh. The rum was all gone now, and so were the chips. Roxette was singing The First Girl On The Moon.
“I guess I should be going,” he said.
She did not move her hand or chin. “If you really want to,” she said.
“I don’t want to,” he said. “But I’ve got to.”
“Stay a little longer.” She wiggled her hand on his shoulder. He looked at her. She had folded her legs up to her, and her pretty feet lay demurely side by side in their awful clunky leather sandals. “Take off those,” he told her, and she readily complied. He reached out and fondled her toes. She sighed.
“I really must be going,” he said again, but his resolution was weaker.
“No,” she said. “Stay here with me tonight. What will you do in your hostel?”
“All right,” he said. “I’ll stay.” He turned his face to see how she would react, and her mouth was already reaching for his. The kiss, as much accidental as intended, sent an electric shock through to the pit of his stomach. They kissed again, closed lipped at first, then open mouthed, tongues slipping into each others’ mouths and twining round each other’s tongues. He could faintly hear his heart hammering.
At last they broke off kissing and she stood up, reaching down to him with both hands. “Let’s dance.”
Pausing only to remove his shoes in order to protect her bare feet, he got up. The music had changed now, it was a deep, slow tune, and they danced to it, arms round each other, pausing in their rhythm only to kiss again. His hands, at the back of her neck, found a hairpin and she bent her neck forward to let her hair fall loose. Her hands too were busy, and he felt them slide up the back of his shirt and caress his bare back. His involuntary movement brought his chest to her breasts, and she rubbed them against him. Turning round, she pressed her back to him, pushing her buttocks into his crotch. His hands went to her breasts. For the first time, feeling them directly, he realised that she was not wearing a bra. As he fondled her breasts through the thin cloth, he wondered if she would pull away. Instead, she thrust her breasts further into his hands and sighed.
Dancing forgotten, and greatly daring, he slid his hands under her T-shirt, and slid them up her taut belly till they encountered her bare breasts. They were small and filled his hands easily and naturally. The nipples were firm, pointed, almost hard, and it was natural to twirl them gently between his fingertips. She gasped, and, alarmed, he almost stepped back.
“No,” she said, “please don’t stop. You don’t know how good that feels.”
He never noticed the particular point when her T shirt came off. Suddenly, she was naked above the waist, facing him, and her bare toes were pressing down on his as her breasts pressed on his chest. Her face was touching his and her arms thrown round his neck, pulling him, irresistibly, towards the large, inviting bed.
When he regained a clear sense of himself he was on his back on the bed and she was straddling him. With surprise he noted that he was bare torsoed – at some point she had removed his shirt. Her breasts hung down and the large brown nipples, very large for such small breasts, touched his chest as she bent to kiss him. His hands tangled in her hair.
“Take off your pants,” she whispered, then moved off him and fumbled at the zipper with her own hands. Before he could move she had his trousers open, had pushed his underwear down, and taken his rigid erection in her hand. Her grip was wildly exciting, more so than anything he had felt before. He felt her, as if in a dream, pulling the trousers and underwear off him with her other hand, the clothes falling off his feet, till he was completely naked but for a wristwatch. She bent over his pelvis and he felt a tiny wet touch flick over the tip of his penis. It took a moment to realise it was her tongue.
His hands were on her shoulders, urging her wordlessly from his penis and down on top of him. She came to him willingly, his hands at the tight brass buttons securing her jeans, till she undid hem herself and he pushed them gently off her buttocks and legs , leaving her in pink panties. His hands slipped under the panties and cupped the twin globes of her buttocks. She moaned and raised her hips so that he could pull the panties away. Instinctively, he tried to remove them as slowly as possible, drawing them down her legs and over her feet, running his hands down her limbs so that she felt their touch all the way from her hips down to her toes. She reached for him again.
In a moment they were lying side by side, their hands, and mouths exploring. She fluttered her eyelashes on his, and then over his cheeks, while his fingers traced her belly with the dimple of her navel. Below, they encountered the wiry pubic hair and might have hesitated, but she humped up her pelvis and opened her thighs. He found her already slippery with moisture and it was easy to slide his finger into her. It was the first time he had ever felt a vagina and he was amazed at how naturally his finger fell into a thrusting rhythm. She sighed and ground her self against his hand. He bent his head and took one of her nipples into his mouth. She moaned, so he did it with the other nipple, still thrusting his finger in and out, and licked the crease at the underside of her breast. His finger encountered a little swelling on the front wall of her vagina, and he began pressing on it with the ball of his finger. She moaned again and began thrusting against his hand frantically. He licked her breast and pressed with his finger until her orgasm finally wound down.
He looked at her as she lay, momentarily spent, her hair and body damp with sweat. The sight inflamed him. She seemed infinitely more desirable now than the made-up young lady who was his classmate, with her legs thrown open and her breasts rising and falling. He slid down until her vulva lay flowering open to his hands when he used them to spread her labia. The smell was earthy, intensely exciting, and the taste, when he licked her, salty and stimulating. He used his tongue in little vertical licks, as he had read in sex manuals, and she responded by pushing up to meet him. He located the clit, a little hard nubbin the touch of his tongue on which made her squirm and push up again. He flicked his tongue across it, and then away, and back again. She orgasmed amazingly quickly, her pubic hair grinding against his lips as she bucked. She lay still again for a moment, then reached down to pull him up to her. When the moment came at last, he found that he was as hard as ever.
He had been afraid he would not be able to find her vagina, and contented himself with rubbing himself over her, belly to belly, chest to breasts, his penis feeling the tug of her pubic hair as it rubbed back and forth through them. Then she did something, changed her position, and he felt the nudging sensation of his glans entering between her wet labia, sliding in her moistness, and then suddenly it was astonishingly easy, her vagina was warm and wet and clasping his penis, the internal ridges rubbing back and forth across the corona of his penis in a rhythm infinitely delicious. The act of losing his virginity was so easy and so beautiful that he lay still for a long moment, just savouring the sensations, before beginning to move back and forth. She moved with him, bucking as he thrust so that their hips met off the bed as he held himself off her chest with his arms. He moved, and she moved, and her vagina clasped his penis in its intense feminine warmth.
He could feel the tension building in his genitals, in the entire pelvis, along the sides of his testes. He tried to slow the rhythm, trying to hold back for her, but she bucked her hips against him, urging him on, and then she was sighing and he too could feel his orgasm coming, passing the point of no return, and he was exploding inside her, shuddering while his pelvic region pulsed and pleasure spread like flames burning his body from the genitals in spreading waves outward, outward. He cried out and slumped onto her, as their orgasms reached a crescendo and ebbed slowly.
Afterwards they lay side by side and touched and kissed, rubbing their feet against each others’ legs, their arms twining round each other. It was nothing like he had ever thought before, this warm, breathing, passionate woman in his arms. After some time she reached for him again.
They never did get to sleep that night.
January 7th, 2011 at 7:50 am
You wrote about your first time in a far more erotic manner than I did, Bill. I especially like the line “her vagina clasped his penis in its intense feminine warmth.” That sensation is probably the male equivalent to women feeling completely filled up.
January 8th, 2011 at 12:53 pm
Great post svetlana! It’s great reading about sex from the girls perspective. For the record, my first time i came literally within seconds of putting my penis in. LMAO that was so embarassing.
January 8th, 2011 at 1:03 pm
I love first time experience descriptions. I wish some of your other readers would contribute their own accounts of the time they lost their virginity.
Maybe you could start a thread specifically for that…
January 8th, 2011 at 2:05 pm
Thanks, William. I think it’s natural to wonder what the sex experience is like for the opposite gender. Too bad that you didn’t get to enjoy the sensation of “her vagina gripping your penis in its intense feminine warmth” the way Bill did for very long. At least you put it in and weren’t a virgin anymore :).
January 8th, 2011 at 2:08 pm
That’s not a bad idea, Bill. I’ll have to think about the best way to do it, whether in a post or a page.
January 9th, 2011 at 11:51 pm
You know, I was lucky in that my first time of actually having sex was such a good experience. Before that I’d had a very similar experience with another woman, but this one, after getting us both naked and then rubbing herself off to two orgasms on me, suddenly decided she didn’t want sex. That was extremely humiliating and put me off trying for several years, so the girl who actually took my virginity from me was doing me a much greater favour than just that. She pretty much rescued me from sexual trauma.
I have sex relatively rarely these days – it’s been over a month as I write this – but usually it’s pretty good, and for that I have to thank that long-ago classmate of mine.
January 10th, 2011 at 5:59 am
Sigh, I’m a Jason, but sadly not that Jason. :)
Nicely told Svetlana.
January 10th, 2011 at 6:44 am
Thanks, Jason.
January 10th, 2011 at 6:49 am
In defense of the first woman, after rubbing herself off to two orgasm, she probably didn’t need sex – but she should have given you a hand job, at least, as a courtesy.
January 17th, 2011 at 9:55 am
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March 27th, 2012 at 10:40 am
My first time was with a friend. She was a pretty girl but I had not feelings of love for her. She had a few boyfriends before me and when I entered her I came with in a minute. Was it great? For the first time it was ok but being so inexperienced I knew it would take a lot more for it to become better. Well it did.