Tag: Oral

Introducing the innocent girl to anal [m/f]

Over the last week or so I've had a great time writing about my time dating this sexually repressed woman and how insanely hot it was to break down her sexual barriers one by one. I'm sad to say I'm just about out of stories about her… but this final (or maybe penultimate) installment might be my favorite one yet. If you want to read the rest of the stories for some background, here they are:

Making her beg / Making her squirt / Eating her out

We'd been dating for ballpark five months, and the sex continued to be phenomenal. I kept pushing the boundaries, she kept resisting and eventually caving in. I came to realize that she loved the process of being corrupted as much as I loved being the corrupter– she was a sub to her core and came the hardest when she was being "forced" to do something that she felt was degrading or wrong. The hottest part was how she'd always end up begging for it– watching this nice Catholic girl implore me to choke her, to call her a whore, to make her squirt– those times remain some of the hottest memories of my life. Read more »

My Affair: The Party, Part I (M/F)

This is the fourth in a series. You can read the first three parts here, here and here.

“Soooo … I’ve been invited to a party.”

The message popped up on my screen with no warning. I had been online waiting for Rachel for several hours, but it was getting late and I was about to sign off thinking she wasn’t going to make it on tonight.

I was a little confused by the message. We have a large circle of friends and there’s a party or gathering of some kind just about every weekend if you want to attend. The fact that she had been invited to a party wasn’t in any way remarkable. However, I knew there must be more to this, so I decided to inquire further.

“Oh?,” I replied. “Whose party? I know that Will was thinking of getting some people together, but I don’t think we’re planning on going.”

“No, this isn’t Will’s party,” she wrote. “This is different.”

The then started telling me about her friend Jenn. Apparently I wasn’t the only one that Rachel had been talking to about her sexual frustrations, fantasies and desires. She had been confiding in Jenn, as well. In fact, Jenn knew all about what Rachel and I had been up to these last few months. Read more »

Nympho Cu[m]slut Girl[F]riend RETURNS!

I've written about my ex-girlfriend Kerry before, but now I have a fresh story to tell! I haven't spoken to her in about 10 years. We dated on and off (mostly on. . .) for about 7 years starting in HS and through college, and then had a FWB/booty call relationship while being best friends for years after college. However, at that point, I had missed my chance to marry her and knew we were never really going to get back together as a couple, so when I met my now wife and started dating her, I had to break things off with Kerry. It was too hard to be so close but not together and it worked out better for both of us to get some space, so we could find our spouse or even be open to a long-term relationship. So I said my peace to her and cut off communication and haven't looked back (other than remembering/fantasizing about some of the crazy things we did to/with each other).

The other day, I went on Facebook to check out my feed and noticed that there was a message in my inbox. I clicked over to the inbox and a message from Kerry was waiting. Her message was short and quick: Read more »

Its just sex [m/f]

The girl of my dream was in front of me standing their with her black lingerie in my hotel room. She is my first and also be my 2nd time to have sex with.

Her beautiful japanese white smooth skin glimmering in the light. Her A cup size breast ,cute face, and slim petite body. All I could do was stare at her in awestruck. She was gorgeous and all mine. As she undressed she snapped me outta my state and told me to undress as well. I no doubt oblige.

As she walk past me to the shower her sweet flowery perfume intoxicated me for moment. She had me at that very point in time. I was infatued by her essence and body. I was being seduced and I enjoyed every moment of it.

We got into to the shower together. The warm water sprayed across her body and mine. I held her and drowned in her sweet flower essence. She grabbed some body soap and lather it onto my chest and erect penis. She stroked my penis slowly at first. I grunted a little bit and whisper her name aya-chan. Read more »

[M4F] The Older Woman

This was almost seven years ago, so I was 48; she was 56. We met on PoF and after exchanging messages for a while (and maybe talking on the phone) we decide to meet. We met at a big strip mall shopping center parking lot. We parked at the very edge of the parking lot, away from all the businesses, but shielded from the road by a high bank. She got out of her car and came and sat in mine.

She had blond hair (yes, I know it probably wasn’t nature anymore) and sky-blue eyes, two of my favorite features on a woman. She was still very striking for her age (an age that I’m now only 14 months away from myself), dressed like she was on her way to a nice dinner, and I liked her right from the start.

We talked for several minutes, and at an appropriate moment, I leaned over and kissed her. She smiled and said “Oh!” I started to lean in again, and this time she met my kiss. Our lips parted and our tongues began probing each other’s mouths. I nestled her face in my hand for a moment and then ran the tips of my fingers down her neck to her breasts. As we kissed, I fondled her breasts, and she began to rub my swelling cock through my pants. Read more »

From that point on she kept at least one hand on the back of my head.

The note read, “Get cleaned up and meet me at the Westin at 7:00. Don’t be late.”

A lipstick imprint of a kiss was her signature. I caught a faint waft of vanilla and perfume. Attached to the note was a room key marked #303. I looked at the clock. It was almost 5:30.

Still a little bewildered I called her. No answer. I sent a text. After several minutes, there was no response. It was Friday night. We usually have some sort of sex to unwind from the week. Still, I imagined a bottle of wine, giving her a couple of spankings, trading oral sex, then watching Star Trek. A normal Friday. Honestly, I was a little annoyed. I had been looking forward to my comfortable blowjob all day.

I was also quite impressed. It took a lot of planning and determination to pull off a stunt like this. Adrisa is usually terrible at surprises. After taking the dogs out I undressed to take a shower. I noticed that my imagination and my anticipation as to what she may have planned had gotten me more aroused than I realized. For a moment I considered quickly jacking off to ease the tension a bit but the time constraint encourages me to think better of the idea. Read more »

A unicorn walks into a swingers club (Part 1) [F41 / Lots of M]

[Hi Readers – if you like a set up to a story, read this whole post. If not, and you just want a description of sex acts, scroll down]

I recently ended a relationship and decided become active again on FetLife (and no, you won't find me there using my name). I looked at some old messages between me and a couple "in the lifestyle". They had reached out to me shortly after I joined the site 8 months ago, and we'd talked about meeting but it never worked out. She's bi, and he's straight, probably a decade older than I, they always play together, and they are very well known in swingers circles. They have a reputation for being lovely people and looked like a lot of fun. I'm curious about being with a woman and a couple like them seemed like a good place to start.

After a moment of debate, I sent them a quick note. I told them I was newly single, interested in perhaps going to an event some day soon, and asked them to let me know when they were attending something local. Turned out, they were going to an event in a local sex / swingers club this past Saturday, and suggested I go as well. I had no child and no plans. Read more »

I [M]et my [f]abulous DirtyPenPal.

Hey GWS folks. This story is coming to you in two parts, don’t worry it’s not one of those lame, “If you like it I’ll write the rest” posts. This story was written in two parts The first section is before the meeting and the second covers the actual meeting. You will get both parts in one post if I can fit it all in. This was at the suggestion of my dirty penpal, since we thought it would be fun to share our story here.

I have been a writer in /r/dirtypenpals for a while and have had a lot of fun creating stories and occasionally getting to know interesting writing partners. One writing partner in particular knew how to get my blood going and vice versa. We wrote a story over many months and when we completed the story, found ourselves getting to know each other. Not full disclosure just little pieces. General areas we were from, what we liked about stories, etc. Then came the question, “Ever met anyone from the sub?” She had but it hadn’t gone anywhere. She had met other folks from other places and had some fun with that. I hadn’t met anyone from the sub and hadn’t met anyone online for a while but for some reason I felt she might be a breakthrough in both areas for me. Read more »

[M4F] My Anal Adventures: Hits and Misses

I didn’t have my first anal sex until I was 45 or 46. I got married at 25 and broached the subject with my wife sometime during the first two years but she wasn’t interested at all (don’t get me started).

However, when I had my first affair, my AP specifically asked me if there were any sexual things I hadn’t tried but wanted to try. She wanted to give herself to me in a way no one else ever had. It was the first experience with anal sex for either of us. We went slow and used lots of lube, but I think it was still at least a little bit uncomfortable for her.

I always waited until after I made her come at least twice before moving to anal. Our best time was once when she was lying flat on her stomach and I was on top of her with my hard cock deep inside her tight ass. I reached around and slid my hand between the bed and her thigh. Then I rubbed her clit until she came again while at the same time filling her ass with my hot cum. Read more »

(F)inally hooked up with (m)y crush part 3: the tables turn

Hi there. I hope you enjoy the conclusion (for now) of this story. Here you can find part 1 and part 2.

He told me that he wanted to give me a slight idea of what he had been through. I helped explain the knot I had used on him and he tied me up the same way I had him. I didn't realize what it was like. I could hardly move my limbs but I could still move my torso around a bit. He blindfolded me before he got to work. From here it's hard to describe what happened. Almost all the information we get from the world is visual and when that's cut off it can be hard to tell what's happening. The mystery of the experience only added to the excitement. Every move of his was a mystery, every touch a surprise. Read more »