Losing (M)y virginity for the second time.. [M/F] | 2016

This experience was a first for me and is more of a prequel to my subsequent adventures but it’s a starting point for some pretty naughty adventures so I will share it.

It had been a long time since I had been with a woman. Over a year. After having been married for almost 10 years and trying for the last 5 years to get things back to something normal after some very bad experiences, something just clicked in my head and I knew it was never going to get better. It was over. I had been faithful during all those years but when I knew it was over I could not see myself having sex with my ex or having sex with others while we were still living together. So I abstained from sex with my ex-wife and other women until we had formally broke up and I had left. I was shattered that my marriage was falling apart even though I was the one that was leaving. After moving I was in no state to be with thinking about being with another women as I dealt with the realisation that my marriage had failed.

It wasn’t until a few months after leaving that I started to feel up to meeting new women. I started getting online and chatting to a few women. By this stage it had been over a year since I had sex (with another person at least :P ) and I felt like a virgin again. Before getting married I had only slept with a handful of women. I had always had a dirty mind and very dirty fantasies but my conservative upbringing suppressed those fantasies. Given that I was single again after almost 12 years I decided it was time to exploit this opportunity and to explore my fantasies.

So I started chatting to a few girls online. I was upfront about my situation and made light of the fact that I was a ‘virgin’. As I continued chatting to a few women I had decided to make an experience of it and there were a few women who were turned on by being the first woman I had touched in a long long time and the first woman I had touched outside my marriage in 12 years. The tease of it all was quite exciting. A few times I almost hooked up with different girls but schedules never seemed to work out. After chatting for a while I sent a message to a girl online her name was Dani whom I noticed in her profile “loved European men” (of which I am descended). She was an alpha-female, up front and used to getting what she wanted. Rather than chit chat online for ever or send message her response was short and sharp, “Loved your profile and your pics. Here’s my phone number call me before someone else gets my attention.” I could tell from that point she was quite direct. I called her nervously and by the end of the phone call we’d organised to catch up for a drink the following night near her house.

We caught up the next night for a drink at a bar and immediately her directness put me at ease. Telling me how ‘cute’ I was. It reemphasised to me that we all have individual likes and dislikes. She found my dark European features as much as a turn on as I found her voluptuous body, her green eyes, her dark hair and her pale skin. Our conversation flowed and we were obviously hitting it off and I decided to take her out to dinner where we kept drinking. I told her about my newly found virginity and how much I was enjoying drawing it out, the tease of it. By the end of the night we both decided it was time to end my drought but we should draw it out just a little more. I wanted her right then but I loved the idea of craving her for a few days more. We were quite drunk at dinner by this time and it didn’t take a lot of nerve for me to lean over across the table and kiss her red lips. Later as my confidence grew my hands crept under the table and touched her thighs. Her thighs parted and I could tell she was receptive so I moved my hand upwards along her inner thighs caressing her legs as I went higher. I wanted to touch her pussy there and then. I wanted to taste her there and then. I want to grab her and push her onto the dining table and take her right there and then in front of all the other patrons. It had been so long since I had tasted a woman and I craved it so much. By this time we were talking about sexual fantasies and experiences and one of her kinks was playing in public so I knew she was ok with me feeling her up in the restaurant. I was wanted her right then and there but I had to remain in control eventually I regained my composure and settled the bill. I started to walk her home.

As we discussed in the restaurant tonight would not be the night but as we walked to her home I asked her ”Maybe you can just give me a taste?”. She smiled knowing exactly what I wanted. She led me into her house and into her bedroom and sat back down on her bed as I stood in front of her. She arched backwards, hitched up her dress and slowly slid her panties down of her hips and down around her legs. I could tell she was as turned on as I was. I could smell her scent in the air and I could see her panties were soaked as she let them drop around her ankles. I marveled at her gorgeous shaved pussy and as she parted her thighs for me to give me a better look. I was hard, my cock wanting to bust through my jeans and fuck her then and there but instead she locked eyes with me with her gorgeous devious green eyes “Just ONE taste!” she reminded me. If I was going to only get one taste I was going to make sure it was a bloody good one. I dropped to my knees and with my hands parting her thighs I ran my tongue from the bottom of her pussy near her arse slowly upwards with one long deliberate lick, my tongue sliding upwards between her amazing bare wet lips lapping up her wetness up to her clit. She was very wet and I enjoyed tasting every drop of her juices from her beautiful cunt. She tasted so sweet and it had been so long since I had tasted a girl. As my mouth clasped over her clit I lost control and started sucking and licking it. I could hear her moaning and squirming underneath me but very quickly she regained her composure and pushed me away. “You’ve had your taste, now you have to wait until next time”.

I made my way home with a smile on my face and with her taste still on my lips, my cock hard and aching to break free and be relieved as I savoured her taste all the way home.

We had organised to catch up a few days later. Luckily, no more bars, no more restaurants. I was meeting at her place. I knew it was going to happen. So I stopped playing leading up to meeting her. This made the tease even more intense and I found myself hard every day all day waiting to lose my virginity (again) with her. When I finally got to her house, we start watching TV and sharing a few wines, eventually after what seemed ages and without being (as) drunk this time around like our first date I start to kiss her. As things heated up I started fondling her and finally we slowly made our way to her bedroom as we roughly pulled our clothes off each other, our clothes littering the hallway towards her bedroom. I had been joking with her since we chatted that it has been so long I might only last 8 seconds and the way I felt then it might not would not be far from the truth. We stumbled onto the bed both of us naked my hands cupping her breasts fondling and squeezing them, kissing her, my mouth trying to get a taste of every inch of her. Like a starving man that has finally been offered the sweetest most decadent dish. I was very hard and wanted to penetrate her immediately. For the first time in a very long time my naked body pressed up against a naked woman’s body. Something I had imagined over and over. I crept downwards slowly, my mouth still tasting her breasts, her stomach until finally I buried my face between her legs and tasted her once more. This time taking my time to savour her taste. Making her wetter and wetter with my tongue my fingers sliding inside her and fucking her as my tongue flicked over her clit. I would like to say I made her cum with my mouth but the truth was I was out of practice (I got my groove back later) and as delicious as she was I needed to fuck her then and there. Eventually, I knelt up on her bed between her legs, pressing my cock against her lips, rubbing it up and down teasing myself. It was finally about to happen. Slowly, deliberately I pressed my hard head of my cock against her lips and slid it into her tight pussy as she looked me in the eye and smiled. I had finally lost my virginity ‘again’!! I would love to say I fucked her for hours in every position but her pussy felt so tight and wet that I was content to fuck her laying on top of her, driving my cock deep into her wet tight cunt over and over until I finally pulled out cumming and unloading a huge load of cum across her stomach and onto her breasts. My fears of being able to last 8 seconds were unfounded and I ended up fucking her for a few minutes! Not a marathon by any stretch… but respectable. :)

We caught up a few times over the next few weeks and it was enjoyable getting comfortable with and exploring a woman’s body again. One time she presents herself to me bent over standing behind her couch, naked apart from her stilettos. She leans back and tells me how much she “… LOVES anal!” In later weeks, months and years (and now) I would have exploited that. If I knew what turned a woman on I would to do my upmost to give her what turns her on immediately. My tongue, my fingers, my cock would be buried deep into her ass before too long. But for some reason I didn’t and I look back at that time as a ‘WTF?’ moment I did not play with her exposed delicious tight asshole. I fucked her from behind as she stood bent over her couch eventually cumming all over her ass cheeks.

After a few weeks we stopped playing together. I was keen to not settle down with anyone. I wanted to explore, I want to fuck, I wanted to make all those dirty fantasies I’ve had since being a young boy come true (and I did mostly) so I was never going to be long term with her. I think she saw me as not being open-minded enough for her (and I found out years later it was because I refused to play with her ass that night. Something I rectified with her a few years down the track.) We caught up again about 2-3 years later. We discussed what we’d been up to since and I told her of some of my subsequent adventures, threesomes, foursomes, public sex, bdsm, etc. She was amazed. She confided with me that she didn’t think I was that open-minded after not playing with her ass. I proposed we catch up so I could make up for it. We caught up and I made sure I gave her ass all the attention she missed the first time, biting her ass cheeks, licking her ass making it wet and getting it ready for a deep hards arse fucking. Pressing my cock into her tight ass and fucking her hard, deep and slow. Finally making her cum all over my mouth as I licked her clit, my fingers fucking her soaking wet cunt while at the same time fucking her tight asshole with her shiny new metallic dildo.

All in all I was glad it was her that took my virginity for the second time. Meeting her kicked started a number of years of sexual debauchery and exploring my sexual fantasies and beyond.