[MF] Losing my ‘virginity’

Several people messaged me asking to share my first time. I hope this is what you were looking for. As I’ve stated in my other posts, I grew up pretty conservative and didn’t come out of my shell until college (like most people, I’d say). Although I fooled around quite a bit, I didn’t have sex until my senior year. Although I enjoyed fooling around, foreplay, oral, etc, I would never go the whole way…I still was a ‘save yourself for marriage’ type of lady.

I had been dating a guy for a few months early in the spring semester, senior year. He was part of a student group I was in and was also pretty conservative and Christian, so he understood the no sex thing and was okay with it. I was only the second girl he’d ever fooled around with…I told him he was my 3rd, but by that point, he was my 5th guy and I had hooked up with 8 girls. So, although he was patient, I was certainly becoming impatient about sex..but I also did want to save myself for marriage. I had been talking about sex with a group of girls from a church group I was in and although I could tell most were even less experienced than I, one of the girls had mentioned that her and her boyfriend have anal sex b/c it’s not considered ‘losing your virginity’, as he’s not putting his penis in your vagina…I was skeptical about all of that, but was definitely desperate to try something else. Ever since one of my first experiences in college that led to rimming and some fingering, I had begun exploring with my own fingers and some toys. A few girls and I had experimented as well, but I had never had a cock or a dildo in my ass. I definitely wanted to do it, though, but wasn’t sure how to approach it with my boyfriend.

Being immature and horny, I thought the best way to do this was to get drunk! The whole week, I worked myself up with playing and using my plugs to prepare for his above-average sized cock. So…the next weekend, we headed to a party with a group of friends. There was lots of drinking and dancing. At one point, late in the evening, I was dancing with my boyfriend and began rubbing his cock over his jeans. He instantly got hard. I whispered in his ear, “Let’s go..I have a surprise for you.” What he didn’t know is that under my jeans and sweater I had a sexy, black bodysuit on along with my biggest plug. Now, he had no idea I was into ass play. Since we were rather conservative, I was embarrassed about it and didn’t really discuss my solo play.

When we got back to my place, he could hardly get in the door and was taking off my clothes. He was kissing me very sloppily with lots of tongue…I knew he was pretty drunk…I was just hoping he could keep it hard. He got my sweater and jeans off, revealing my bodysuit. He stopped and oohed and aahed a bit. I smiled and told him to sit on the bed. I pulled off his sweater and t-shirt, then I went for his belt, and unzipped his jeans. As I got them down over his groin, his cock stood at attention through his boxer briefs. I got them off and slowly began teasing his cock with my tongue. Up and down his shaft I went…tickling the head of his cock with my swirling tongue. I continued this while slowly stroking him. The teasing got too much and he pulled me up on the bed. He unsnapped my bodysuit and pulled it over my head. He started on my nipples while sliding two fingers inside of me. After making me super wet from playing with my g-spot, I told him to suck on my clit. As he went down on me, he saw the plug sticking out of my ass. He asked me what it was. I played coy and laughed, “oohh I forgot it was in there. I play with it sometimes b/c it feels really good. Do you want me to take it out and play?” He agreed somewhat tentatively and I hopped up and took it out and made sure everything was clean down there. I grabbed some lube and came back into the bed.

I laid back and told him to suck on my clit and finger my ass. Having a man’s fingers in there..felt amazing. He was forceful but not rough and he really prepared me for what was next. The more forceful he became with his fingers, the harder he sucked and flicked my clit. He quickly brought me to orgasm. After I caught my breath, I said…’now fuck my ass!’ He stopped and said, “really?’

‘Yes..i want to feel your cock inside of me!’ I helped him lube his cock. He reached the tip of his penis into me. It was tight but not painful, as he inched deeper inside of me is when the stretching started to hurt a bit. I grimaced and he stopped. ‘Just a little slower’ I grabbed his hips as he slowly continued. When he got himself the whole way inside, I held on tight to him and said, ‘just hold there’ My ass was pulsating as he stretched me like I hadn’t ever been before. After a few seconds, the pain began to subside. I told him to continue slowly. For the next couple minutes he thrust his hips loosening me up with each movement. After a few minutes and the pain gone..it just began to feel amazing. I felt so full and all of the nerve endings were exploding with pleasure. He began pumping harder and faster. I started rubbing my clit furiously. By this point, he had really stretched me open and was pounding me really hard. Finally, he pulled himself into me and I could feel his cum explode inside of me. He got up and ran to the bathroom to clean himself off. I lay there and finished myself off. It was quite a way to lose my ‘virginity’!

After that, we had many more similar adventures, until we broke up right after graduation.

Hope you all enjoyed hearing about my first time and I’ve enjoyed answering your questions, so keep them coming!

Source: reddit.com/r/gonewildstories/comments/husp95/mf_losing_my_virginity