Lost my virginity to an older woman [MF]

This just happened yesterday and I just need to tell someone, so hopefully you don’t mind and maybe you’ll even enjoy it.

As the title suggests, I lost my virginity yesterday afternoon to an older woman – I think she said she was 43. I’m a 22 year old guy from NJ, though that probably doesn’t matter. I have social anxiety and I’m generally pretty awkward around people so this really caught me as a surprise and I still have to remind myself it actually happened.

Anyway, onto the story..

There’s a small pizza shop about 20 minutes away from my house that my family orders from when we wanted to pickup a quick pizza. Previously, the cashiers at the pizza shop are college students that are home for the summer looking for a summer job. Since school has started back up (mid-August?), the cashier (Christine) has been the same woman each time my family has gone there. We went there a couple of times, enough for Christine to recognize us, our names and our order.

The strip club got her all excited.

I really enjoy reading this sub and figured I keep sharing a few of my stories.

I was talking to an 18 year old Dominican chick, short cute, she was not fat but she wasn’t skinny, she had huge DD boobs. One night I was out drinking and having a good time with a good friend of mine when she texts me to see what I was up that Friday night. My buddy told me to invite her and let’s all hang out, she quickly took an Uber and met us at the bar.

After hanging out at the bar for a while we get the crazy idea of going to a strip club ! Me and my buddy stop and get some cash out and she’s never been to one and we made it a great experience for her, she was pretty worked up and I couldn’t wait to get her home. After the club she drives me home, I was pretty drunk and tired from work.

Not Yet [MF] [POV] [x-post r/sexystories]

I wake up to his warm hands caressing me under the sheets. First running up my arm, then back down my side, and over my hip. I snuggle back against him, feeling his already hard cock against my ass. As his hands continue their early morning exploration, he bends his head and whispers in my ear. “Good morning, my pet. Did you sleep well?”

“Mmmm,” is all I can respond. His hands have changed course, now cupping my breast. He traces my nipple with the tip of his finger.

“I asked you a question, pet.” His voice a bit rougher. “Did you sleep well?”

“Yes!” I gasp sharply as he pinches my nipple with his thumb and forefinger, making my back arch and my pussy throb. I can feel myself getting wet already, and yet I know this is only the beginning.

“Good,” he replies, soothing my pain with his thumb, rolling it lightly over the hard peak. “You’re going to need your strength today.”

The Phone [MF] [PHONE SEX] [COWORKER]

The other day, I sat in my room crying to myself and wondering what did I do to deserve this. All of this time I had spent supporting him and giving everything I had to our relationship. I sleep alone a lot of nights because he told me that he had to work late. I spent holidays alone because he told me that he had to go out of town for business. Some nights I would cook dinner knowing that his face would be absent from the other end of the table. Sitting on my bed, I became frozen as I stared into the open space in which we used to share. He left me for her, Amy the intern who helped him with all his projects. The look in his eyes as words formed from his lips telling me that he no longer loved me, shocked my heart. As he walked out the door, he turned to me and said, “Maybe if you lose some weight you can get another man to fuck you.” The door closed and I stood there in silence with petals of tears running down my cheek. How could he just abandon the love that we built over all these years for an intern? Suddenly I went into a deep depression that seem like years but was only for a few weeks.
Sitting at the ice cream parlor, I devoured two big bowls of vanilla fudge. As I put each spoonful into my mouth I cried. The waitress kept asking me am I okay but I would just nod and mumble yes. “Excuse me may I sit here?” a deep rough voice said as I held my spoon in mid air. I didn’t respond because, I didn’t know how to respond. Staring at my bowl I refused to look up and instead shoved the spoonful of ice cream into my mouth. “So what flavor of ice cream is that?” he asked as I began to move my head slightly to look up. “Its vanilla fudge”, I said softly as I began to notice his face. It was Glen from my job. Glen is a man that all of the ladies follow at work, they love his charm and good looks. His hair is jet black with lots of curls and he has gem colored green eyes. He is handsome but he has never spoken to me before at work and feel confused about him sitting across from me. “You haven’t been to work in a few days, is everything okay?”, he asks as he dips his spoon into my ice cream bowl. “I am okay, just been busy”, as reply to him in a soft tone looking at him intensely. How does he know I haven’t been to work, this man doesn’t know me nor has he ever even acknowledged my existence. “Btw you have very good choice in ice cream”, as he took another spoonful from my bowl. In my mind I am thinking what does he want from a broken woman and I wished he would go away. Then all of sudden he stood up, “I leave you with your ice cream for now but call me later” as he placed a card on the table then walked away. I gazed at the card for a moment thinking why would I want to call him. What is he wanting? before I could ask myself anymore questions I quickly grabbed the card and put in my purse.
Later that night, I kept thinking about the card in my purse. If I called him what would we talk about? Him and I have nothing in common at all. So before I scared myself out the whole idea, I took out the card and called him. “Hello April, how are you this evening” he said as breathed into the phone saying hello. Silence for a few seconds and he says,”What are you wearing tonight?” as I could hear breathes escape from his lips while on the phone. Startled at first I began to describe what I was wearing. “Well I am wearing a black crop top and skirt.” He paused in the midst of his breathing and asked could I remove my top. I wanted to say no and hang up the phone however I slowly began to pull my top over my head. “You should always be comfortable when talking to me,” he said as I sat in my chair like a kid waiting for the next instruction. “Are your nipples hard right now?” he asked as I began to look down at my curvy breasts. I acknowledged they were hard with a soft, “Yes.” Then he told me to rub my nipples in circles and tell him how it feels. Feeling a little reluctant, I began to do what he wants, “My nipples feel soft as I glide my finger over each one,” I said as my fingers went randomly over my nipples as I sat in my chair firmly. “My dick is so hard baby, let me rub it all on your nipples,” as he began to breathe harder into the phone. My pussy began to throb as his voice echoed through my whole body. “Spread your legs, open that pussy wide, and rub that clit baby,” he said as I started to hear him stroking his dick up and down. I told him my fingers were rubbing my clit and that he could slide in at any time. He then said to me, “Let me slide in that fat pussy baby, ” as he began to moan louder in to the phone. My voice started to tremble as I felt that connection of both of us cumming at the same time. “Cum for me baby,” he said as I started to moan while rubbing my clit faster and then exploding. He came quickly after me and told me that he had to go. Feeling confused I took it as he used me for his pleasure. I then crawled into my bed and just stared up looking at the ceiling thinking about what I did with Glen over the phone.
The next day I couldn’t help but to keep thinking about the phone call with Glen. Then suddenly a stack of papers slammed on my desk at work. “Glen said to bring this paperwork to him on the third floor,” the clerk said as I began to pick up the papers. I shuffled off to the third floor and as soon as I stepped off the elevator there was Glen in an empty room naked. He looked at me and smiled then motioned for me to come closer. Standing before him, I looked into his eyes and he said,” This is my company and you are mine now, close the door.”

Not Yet [Str8] [MF] [Fsub]

I wake up to his warm hands caressing me under the sheets. First running up my arm, then back down my side, and over my hip. I snuggle back against him, feeling his already hard cock against my ass. As his hands continue their early morning exploration, he bends his head and whispers in my ear. “Good morning, my pet. Did you sleep well?”

“Mmmm,” is all I can respond. His hands have changed course, now cupping my breast. He traces my nipple with the tip of his finger.

“I asked you a question, pet.” His voice a bit rougher. “Did you sleep well?”

“Yes!” I gasp sharply as he pinches my nipple with his thumb and forefinger, making my back arch and my pussy throb. I can feel myself getting wet already, and yet I know this is only the beginning.

“Good,” he replies, soothing my pain with his thumb, rolling it lightly over the hard peak. “You’re going to need your strength today.”

A Warrior Kneels [FMFdom]

The horse lifted his head and snorted with a warning to his Mistress who knelt at the edge of the stream drinking her fill. Green eyes narrowed as she grew still, a hand drifted to the sword at her side as she listened to the surrounding forest. The large warhorse shifted closer to her in a protective stance and her small form rose to her feet with a slow, lithe grace.
Her gloved hand remained upon the hilt of her sword and with one gesture of her other hand the black warhorse melted into the trees at the edge of the creek side.
She stepped into the underbrush on the opposite side of where the horse went and she grew still and waited as the one who approached sounded like a whole army. She knew it was one person, mounted and not being wary nor quiet and that puzzled her as the lands were in a grave state of unrest at this time.
Green eyes watched the brown horse come into the clearing and the man atop the horse slid off with a jingle of spurs and mail. She could see the light sword strapped to his back and his long dark hair was bound into a pony tail. He knelt at the water’s edge and drank from his cupped hands but she knew he knew she was present and she tensed, ready to fight.

It doesn’t get better than fucking older women.

Excuse the details, but I feel it all works together well. I’ve always wanted to tell this story. It’s long!

At the start of this year I ended up staring at the ceiling of a hospital with a health complication, it kept me there for the better part of the week. I had recently gone through a break-up with a long-term girlfriend and because I moved cities with this girlfriend I never put much effort into friendship / social circles. I didn’t feel like I needed to when with her.
We would typically hang out with one another visiting restaurants and cafes until one day she unexpectedly dumped me.
It was a real “oh shit” moment in my life, living in a city of 4 million people not knowing a single soul makes you panic just a little.

He showed me his true colours last night, and they’re incredible (F21/M)

Some of you might have read my last tale about getting four dicks in one night. The response was pretty exciting, and I definitely loved hearing how much you guys all loved it… So I’ve thrown off all the shame I was feeling before – I guess there’s really no better place for a slut than on r/gonewildstories!

I was out in this tiny late night bar last night. It was full of great people, and I ended up losing track of the guy friend I was with on the dance floor. As I stepped outside for a breath of fresh air, two arms enveloped me from behind. I turned with a smile expecting to see my friend Johnny, but instead it’s a guy that I slept with once or twice in the past.
We have a pleasant chat, but honestly, I’m more interested in scouring the patrons outside for my buddy.

That is, until he bends in close and says, “so, hey… Are you still single? Is this one of those nights where you… Y’know…”

I feel a little tingle of excitement run up my back. I hadn’t even been thinking about jumping back into bed with Richard, but now I was.

My first oral report

I’ve just started seeing this guy and I don’t know how else to say this, but I am absolutely in love with his cock. I want to spend all day on my knees worshipping him with my hands and mouth, making him cum and swallowing every last drop. It’s nice and thick and the perfect size, and so so smooth when he’s nice had hard.

I’ve only been with two guys before, my high school boyfriend for two years and then my boyfriend my freshman year but we broke up at the end of my freshman year and I just haven’t been with anyone since. I just started my junior year so I’ve been very lonely for a very long time. After the breakup I kind of stopped taking care of myself and gained a bit of weight but this summer I decided to put an end to that and really dedicated myself to the gym and so by mid August, my body was super tight and probably better than when I was in high school.