Losing virginity, with a (m)il(f).

After reading a number of stories here, I decided to tell you one of my own.

It was a summer night and I was working in direct sales in a tourist place. A short, chubby, long-haired blonde comes along and stares at the promotional video that was running. She literally stood there and said nothing. I knew I had a sale. So we start chatting… Yeah, you can do this; no, it's not dangerous; nobody died so far. She informs me she would likely bring her friend along and they will buy their tickets when they come back.

Except they didn't. She bought the tickets a bit further down the road, as I learned when they turn up for the ride.

Now, as for her friend… While I couldn't see her body at first, as it was covered in some clothes, she did leave a good impression as she was moving with grace. They get on the boat and sit down, the guys on the boat do the usual preparations, and amidst that, the brunette says she is kind of afraid, to which I reply: "Well, guys, I hope you can get her wet…" Without any bad intentions. I was a virgin, hey! And off they went.

I grabbed something to eat and did my job, selling more stuff and taking in a lot of water as it was scorching, and in about an hour, they come back. The kicker was the fact the brunette comes back smiling and waves to me, telling me she had, in fact, gotten wet, and proceeds to pull out her bra she had to change out of, and shows it to me. I help them out of the boat and do some smalltalk and they head off.

The following day, my colleagues and me are sitting and the two reappear. I get a weird look and a smile and they go to the beach. Same thing when they came back.

Day three, we're chilling again and I see the two coming. The brunette just comes to us and drops in my lap and tells me to come and get a drink that evening. I say I will be there, but as it turns out, I have an emergency and can't do a thing.

So, on the next day, she comes there alone and asks where I've been. I start explaining, when she tells me "Shhhh…" and french kisses me in the middle of the road, leaving me with yet another invitation and a "This is my last night here."

I get there after work, the two of them are waiting and drinking. She's in a black dress, high heels, minimal makeup, fruit scent perfume and fashionable shoes combo and I freaking melt, knowing I'll get to have fun with her soon enough. Cue smalltalk. She says something to her friend in a language I couldn't understand and we agree to hit the beach on the other side of town. So we walk and she begins to act as a girl, holding hands and such nonsense. I comply and take her hand, even if it feels strange. She's older than I am. And I don't like holding hands.

Anyway, we walk and talk, I tell her "I'm a virgin" and "I hope you won't be disappointed by the fact I am", and she compliments me on being honest and tells me not to worry at all.

As we get to the beach and find a secluded spot in the darkness of the night, she pulls her dress up and takes her panties off, putting them in the bag. She proceeds to get down on her knees and pulls my pants down and when my cock sprang out, she utters: "Oh, you're ready!" and gets down on me. I was feeling kind of weird, seeing her, in the dim light of the moon and the light coming from the nearby hotels, take all of me in her mouth. As I didn't want to cum that very moment, I started phasing my thoughts out and just enjoyed. She was playing with herself one moment and going over my body the next, all while stroking me and blowing me without a single word. All I could hear was the wind, the waves and her moans.

When I had enough, I said it was time for me to return the favor. Being a bookworm, I knew what to hit, and that's what I did. Her clit got a lengthy and pleasing tease and workout from my tongue and my lips. I used my lips to suck on it, my tongue to nibble on it, hell, even my nose to change it up a bit. She was exstatic and got her first orgasm of the night.

She wanted me to get behind her and fuck her. I put on a condom and went in. It felt nice. Warm. And natural. So she starts going faster and faster. I keep her tempo and hit her as deep as I can. When she orgasms, I lay down (as I don't want her knees to suffer) and she positions herself over my mouth. I go down once again and soon enough, she's on my cock again, cowgirl style. My hands go to her nipples and play around with them, I grasp her tits and caress her back. And let me tell you, for an older woman, she was in SHAPE. Not an ounce of fat. She was fucking hot! So I gently pull her shoulders down, closer to me, and press a kiss on her lips, holding her back while she's pushing herself on me. Not much passes and she whispers "What do you want me to do to you?" in my ear. I get kind of psyched up and tell her: "I want your ass." She refuses but rebutts (PUN INTENDED) with a titjob. Her tits were natural and perky, and at her age especially… it was miraculous! So I'm getting a titjob and play with her hair, neck and tits. I loved her nipples! She mounts again and goes hard on me, while asking what I do in my free time – implying I should have come by then, to which I answer "Well, nothing special… eat and sleep." – which was the truth. Shortly after, another orgasm sends her body into overload. Muscles twitching, moisture all over, and she's spent. She says she wants me to come and gets down on me in hopes doing it as fast as possible. As it was, it didn't work so I had to jerk off over her and we ended up getting some cum over her throat and her marvellous tits. As it was slowly going down her belly, she got her dress and put it on.

We head back to the hotel she was staying at. On the way there, we see a woman I know and knows me and I'm like "OMG this is the last person I needed to see!"… and she says "Don't worry, I'm pretty!" with a winner tone in her voice. :D

Being a gentleman, I didn't want to ask this, but I somehow found the courage and blurted out: "While these are some questions I wouldn't ask a lady, I am very interested and hope you can answer these…" She was "Sure, go ahead." It was then I learned she was 51, (where I would have said 40 or younger); she had not been with a man in the last 2 months and if she were in a relationship, she wouldn't have done this, and that a former virgin was able to make her cum 5 times in the scope of about 2 hours. Yep, high standards set from the start.

Right now, she's back to her work, And yoga and gym. And her daughter, who is almost my age… and looks like her mom, just younger and possibly even more hot. Oh, and I was 21 at the time, if that's relevant.

Source: reddit.com/r/gonewildstories/comments/30pw3f/losing_virginity_with_a_milf