When I met Samantha she was 21. I was 35. I remember meeting her for our first date. She is a natural blonde but back then she was a brunette. She had the brightest most stunning piercing blue eyes I’ve ever seen on a girl. I was a bit taken aback when I met her by her eyes. The biggest turn on for me is a girl with gorgeous eyes and everything else is secondary. Our first date went well and it was as I was walking her back to her car that she sheepishly tells me that she was a virgin. We started dating but we held off having sex. I liked the thought of drawing it out. I wanted to make it special for her but to be honest I also liked the tease of keeping her a virgin for a while.
Just because she was a virgin it didn’t mean she wasn’t a dirty minded girl. We still played all the time while we waited for the right time to go all the way. I loved eating her virgin pussy and making her cum all over my mouth simply by licking her clit and pussy over and over. There was something very sexy about tasting her and knowing I could make her cum even though she was still a virgin. I could not get enough of her sweet virgin cunt. One time before I took her virginity I remember having her half naked on my bed. I was fucking her gorgeous big breasts as she squeezed them around my cock. She’d constantly bring her head forward to lick the head of my cock as it pierced her tits. I was close to cumming and I moaned to her that I was going to cum. She may have been a virgin but she made sure her mouth was wide open and her tongue right out ready to take every drop of cum in her mouth. As my hot load erupted she bent her head down to make sure my load landed in her mouth and on her tongue. I came in her mouth, on her tongue and lips, across her face and even in her eye (to this day she won’t let me forget it). She was a good virgin girl and I told her so as she lapped up my cum from her lips with her tongue and scooping up the sticky goodness from all over her face with her fingers and licking up every drop from each finger. Not often an older man like me gets to play with a young virgin girl who craved my cum so much.
Given we were going to wait a while I was going to savour my delicious virgin girl for as long as possible. When it finally came time to go all the way we made an event of it. I took her away for a few days and we stayed in a nice hotel. The plan was for us to go and have a nice dinner and then to have her first time afterwards. We both dressed up and were about to head out to dinner. She was looking gorgeous and I couldn’t help having a taste of her before we headed out. I laid her back onto the bed and hitched up her dress and pulled her panties off her and down her legs. I remember licking her pussy making it nice and wet. It was supposed to be a teaser before we went out to dinner but I lost control and kept licking her. I cupped my mouth over her clit licking, sucking and flicking my tongue over her clit nice and fast in the way I knew would make her cum. She was getting worked up and her moans were getting louder. I knew she was close and her taste and her arousal also had me rock hard too. Finally, as she grabbed the back of my head and pushed my mouth deep into her pussy she came all over my mouth and tongue with her soaking wet virgin cunt. It would be the last time I tasted her young virgin pussy. I looked down at her and she looked so sexy. She looked so relaxed basking in the afterglow of her orgasm. Her eyes were closed and her legs were still spread nice and wide and her pussy was glistening wet with her juices and tempting me. I couldn’t help myself. I pulled my pants off releasing my hard cock kneeling between her legs. I pulled her dress down dress from under her and slipped it off her. At this point I still was not intending on going all the way, I only wanted to tease her and myself a little before we went out to dinner. I started rubbing my hard cock against and between her wet pussy lips and clit soaking up all her juices with my throbbing shaft. Her cunt was so wet and inviting and it was at that point where I finally lost control. Instead of waiting until after dinner I pressed the head of my cock against her wet lips and slowly, gently, slid my cock inside her tight wet virgin pussy. She moaned out loud while wrapping her arms tightly around me as she welcomed my cock into her virgin pussy. I slowly, slowly pushed deeper and deeper until finally I had my cock deep inside her. I lay on top of her without moving for a few seconds and let her get comfortable before I started fucking her slowly and gently. She felt so wet and tight and I knew I was not going to last very long even while trying to fuck her nice and slow. I soon lost control and I came hard unloading my first load of cum deep into her no longer virgin pussy. I remember her crying afterwards at dinner because of the emotion of finally losing her virginity. Not often I’d be ok with a girl crying after sex! We spent the rest of the few days away fucking in every possible position she had wanted to try for so long in her dirty mind.
Virgin she might have been but she was always very dirty minded and I started to open up her boundaries letting her fulfil some of her fantasies. I remember the first time she let anyone fuck her arse. It was actually a few months after we broke up. We occasionally got together and had some fun together. She had asked me out with her friends for some drinks in Melbourne. There were some other younger guys out with them that night. I could see some of them were very interested in her and were trying to hit on her. I sat back observing. I knew she was going to be coming home with me.
She was dressed very sexy in a free flowing floral dress that hung just perfectly over her curvy hips. We ended up at my house both drunk. Usually, I’d take her slowly. Make her cum once or even twice while I licked her before I fucked her or let myself cum. But because we were both drunk things happened a little differently. As soon as we got into my room I pushed her onto my bed on all fours. I hitched up her dress over her hips and pulled her panties down over her thighs and around her ankles exposing her ass and pussy to me. I fondled her cunt from behind and could feel she was soaking wet and aching to be fucked. I pressed up behind her grabbing her amazing arse cheeks and slide my cock inside her pussy from behind. My god she felt so good. I started driving my cock deep inside her with long hard deep thrusts. Each thrust deep inside her shaking her ass cheeks. There was something very sexy about having half her clothes on and her dress still hitched over her arse and hips which I knew was going to make me cum if I didn’t stop soon. So I pulled out and while pulling her panties off her ankles and onto the floor I started licking her pussy from behind to give me some time to pull back from the edge as I didn’t want to cum too soon.
I ran my tongue between her wet lips from behind while I parted her legs a little more so I could get good access. Up and down along her gorgeous young wet slit from behind. My tongue would slightly lick her arse hole as I ran it up and down and I could hear her moan our every time. I realised she was enjoying her arse being licked a lot and I started to concentrate on her arsehole. My tongue would lick her arsehole and continued making it wet while she would continue to squirm and moan. I slid my tongue into her arse a little and fucked her arse gently with my tongue and her approving moans got even louder. I continued to lick her arse and pussy from behind for ages making her arse and pussy both soaking wet. Eventually, with her face buried into the bed I heard her ask me, “Do you want to try and fuck my arse?”, as she leaned back with her hands and spread her arse cheeks presenting me her virgin arse hole to fuck. I didn’t need to be asked twice and with her arse nicely lubricated by my mouth and tongue I kneeled behind her and pressed the head of my cock against her tight wet hole. Slowly, I guided my cock into her arse and after the initial resistance she relaxed enough so that I could get the head of my cock into her tight arse. I pushed my cock inside her a little deeper and she moaned out loud as she let go of her arse cheeks allowing them to engulf my cock. Slowly, inch by inch I buried my cock further inside her tight virgin arse. I started fucking her arse with long slow strokes as I marvelled at how well she’s done taking a cock in her arse for the first time. As I built up rhythm I thrust deeper and deeper insider her. It would have been understandable for her to ask me to stop or slow down but she didn’t and I could tell from her moans that her pleasure was out weighing her pain or discomfort. She took my entire shaft in her tight arse as hard and deep as I needed to. As I came close to cumming I lost control and I started fucking her with rougher, harder and deeper strokes. Each animal thrust inside her arse making my balls smack up against her cunt loudly and jolting her whole body until I finally unloaded a huge load of hot cum deep into her tight arse. I collapsed on top of her with my still hard cock buried in her arse. That was the night I took her anal virginity.
Anyway that is how I took Samantha’s virginity. We’ve caught up lots of times since and we had many more dirty adventures. We still speak to this day. She has had several boyfriends since then and is seeing someone now but I will always have been her first.
Source: reddit.com/r/gonewildstories/comments/5wl1ea/older_man_savouring_and_then_taking_her_virginity
Fun fact: the word “virgin” and it’s derivatives appear 22 times in this story (24 if you count the title).
After about the 10th occurrence, I checked out.