Anal Archives — Page 722 of 957 — NSFW story

[FM] Not the usual kind of “blind date” (Part 2)

(This is continued from right where Part 1 left off. The link to the first part is in the comments below)

“I have something for you, if you want it.”

I was so overwhelmed from all the excitement, I didn’t really know what to say in reply, and it was difficult to hear his words clearly through my heavy breaths and still thunderous heartbeat, feeling like it would explode out of my chest.

His hand tightened around my throat, not enough to cut off my air or hurt, but just forcefully enough to bring me back to the moment; his tightened grasp was enough to make me really see him, to come out of my dazed thoughts. His face hovered within an inch of mine, his warm breath touching my lips, making me want to feel his lips pressed to mine again, yet even as I tried, I found that he held me down to the bed. I continued involuntarily grinding my hips as much as he would allow me to, pressed so tightly as he was to me in missionary on the bed. He had creampied me a moment before and he was still hard. He had made me climax multiple times since he had walked through the door, and my body still wanted more; needed more. Read more »

[MF] Pittsburgh Part 2 {cheating} {anal}

Previously, [I posted my encounter with Tara in Pittsburgh](https://www.reddit.com/r/gonewildstories/comments/arrxo0/mf_pittsburgh_part_1/). She told her friend Bethany about our adventure, calling me her human jack-hammer, which I will accept that as a term of endearment. A few weeks after our fun, Tara went dark. Shit, ghosted I thought, but then I got a new message notification in Kik. It was her friend Bethany. Tara had an OpSec failure – a twitter account that her husband discovered. Who uses twitter for anything like this? Anyway, Tara had relayed my Kik name to Bethany to let me know.

Bethany and I chatted, we got to talking about our past experiences, what lead us to do this, and so on. Turns out, she was a bit of a freak…

A few weeks later and I had another trip to Pittsburgh come up. I asked Beth if Tara would be available, and she said no fucking way, that Tara was in deep shit and trying to hold it together. I jokingly (but not really) suggested Bethany and I meet up instead. She wasn’t joking when she agreed. I was worried it would affect their friendship, but Beth assured me it would not, that they had shared guys before with no issue. Score! Read more »

[MF] Pittsburgh Part 1

During a period of my career, I was flying from city to city, and sometimes I lost track of when and where I was. This happened to me on the 3rd leg of a 5 city trip, where I found myself arriving at a hotel at around 10am, with no meeting until 1pm. I was in Pittsburgh. I thought quickly, haven’t I been chatting with someone in Pittsburgh? Yes! Tara! I met her on Ashley Madison a while back, on a previous trip to Pittsburgh, but the timing didn’t work out. What were the odds she would be free right here and right now?

I sent the text. “Hey! Guess where I am!”

She replied almost right away “you are in town?!? Why didn’t you tell me ahead of time?!”

“Well, to be honest, I forgot Pittsburgh was on my agenda. But I’m free until 1, what are you up to?”

Now our chats had been very explicit, lots of boob, pussy, and dick pic exchanges, so I was very much looking forward to seeing her in person. She wasn’t traditionally “hot”. She was cute, but a smaller BBW. Definitely someone I wanted to fuck, even if she wasn’t at the top of my mind at all times. Read more »

My first [T]ime having sex with a [M]ale.

So first, about me: I’m a 23-year-old trans girl, I started living full time as a female two (and a half) years ago. Before that, I spent about two years on aggressive hormone therapy (which I am still on today). I’m 5’8, blonde hair, blue eyes, 130 pounds, perky B cup breasts, and a really big heart-shaped ass that stretches out my skirts and that I’m told looks exceptionally feminine.

Up to only a few months ago, I was dating females. Granted, it was harder for me to make sexual connections after I began to transition and have a more feminine appearance of my own, but there really are plenty of females out there who like to play around with trans girls.

I’ve always fantasized about men. As early as middle school, even as I was only just beginning to scrape the surface of my sexuality and gender, many of my masturbation fantasies involved me being in a feminine role and doing things for men. The thing is, the men in my fantasies had always been sort of generic. I was masturbating to the **idea** of a man finding me attractive and having sex with me as if I were a girl. I never really tried to imagine a face or a type of body. Just the fact of a guy wanting me and putting his cock inside me. Read more »

Hotel sex fueled weekend. Part 1 [MF]

Coming off our excellent [first successful anal sex attempt](https://www.reddit.com/r/gonewildstories/comments/am8q26/first_successful_night_of_anal_mf/?st=JS8BB5MJ&sh=d8f8ea60), she’s been extremely horny lately. I got back from class on Friday (Jan 25) and her car was in the driveway. She doesn’t get off until 5 and home by 5:15ish so it was unusual. When I walk in the door I called her name and I hear from the bedroom “in here!” She’s on the bed still in her pharmacy clothes bouncing on her knees like a little kid with her arms out towards me. She pulls me down and sits on my stomach asking about my day with that sweet scent filling my nose. Brittany’s hands are on my chest while she squeezes me with her knees leaning in for a kiss. “I’m off for the rest of the day. It’s just you and me tonight” as she removes her glasses and let’s her hair down. The baby was at her dads for another kids birthday Saturday morning. I asked what she wanted to do when she hits me a plan she already had in motion. She got us a room at the Roosevelt hotel. Really nice place, central location, great area for night life. Read more »

Happy Valentine’s Day Birthday to [M]e from my wi[F]e – with promised pics

Part one

[https://www.reddit.com/r/gonewildstories/comments/aqm54f/no_fair_my_wife_and_i_teasing_each_other/](https://www.reddit.com/r/gonewildstories/comments/aqm54f/no_fair_my_wife_and_i_teasing_each_other/)

Part two

[https://www.reddit.com/r/gonewildstories/comments/ar2u0m/my_wifes_release/](https://www.reddit.com/r/gonewildstories/comments/ar2u0m/my_wifes_release/)

So my birthday is Valentines Day. Normally we focus more on my birthday and focus our couple stuff on our anniversary. However, I didn’t really want to do a big birthday party this year and especially didn’t given the events of the last two days. This birthday was going to be all about us, and as I later found out she planned it to be all about pleasing me.

It started in the morning. I woke up cuddled behind her at about five AM. Now, given her great ass I love to cuddle up against it, and in the past there had been an issue where I tried to have sex from that position but it just never worked out very well. It’s one we can do after we have already been having sex, but it needs significant lubrication. This morning though, she was dripping and I was able to slide right in. In fact, she has been showing me how wet she is constantly throughout the last several days, and telling me I’ve created a monster! We had a quickie first thing in the morning and she said “Happy birthday, you can have me whenever you want today, Daddy” We went back to bed for a bit. Read more »

[F]irst time butt plug & anal experience at Valentine’s Day with [M]y bf ♡

Heyhey! ☆
I just had my first butt plug and anal experience on Valentine’s Day. My boyfriend 24 and me, female 22 talked about this for some time now and we finally ordered a butt plug tail a few days ago.
I loved the imagination of having two or more things inside of me, just the fantasy of having all my holes filled.

So, for our Valentine’s Day we wanted to try something new. We ordered a Onahole from tenga for my boyfriend and a wig and a tail butt plug for myself. So we started with drinking alcohol and playing Mario kart and super smash bros drinking games. I was a little bit scared because I never had anything in my butt, but I was also extremely wet and horny from the imagination to have double penetration while looking cute with my tail. So as we’re getting more drunk we started playing dirty games like truth or dare, while I wore my black wig. Normally I have blonde hair so I looked like a different person. Read more »

[MF] valentines dinner leads to first time anal play and wearing lingerie (long, first post)

So a little background, my girlfriend and I have been together for going on 3 years. She’s very fun and adventurous, not tall but not short, great shape and an amazing ass. I’m 6ft 4 and am in pretty great shape as well. For some time now we have tossed around the idea of lingerie and other sexy ideas. So last night seemed like a good opportunity to shoot my shot and give her a nice piece of lingerie.

Last night we celebrated valentines at my place. I made a nice dinner and we enjoyed a few cocktails. When she first arrived i was floored at her outfit. Her hair was up and she was wearing a very short dress, barely covering her ass. I was instantly getting turned on. We decided to exchange gifts right away. I’m not going to lie my heart was pounding and when she saw what I had gotten her, her face lit up and she said she loved it! She also had decided to order some for the occasion but didn’t ship in time but she did show me what she had ordered and I cannot wait for them to arrive!This set the tone for the rest of the evening and I could feel the sexual tension start to grow. Read more »

Valentine’s Day is for lust [FM]

I suppose Valentine’s Day is supposed to be for couples and love, but when you’re single it’s convincing your FWB to ram your ass hard in the back of his car.

It only took two dirty snaps of my ass in a dress to have him racing to pick me up at night. Normally we would ride around in his car for a bit before the fun started, but tonight he drove straight to our favorite quiet park.

I tease him a bit for being so excited, at this point he’s so hot and bothered he could careless and the second his car was in park his hands were reaching for me.

I look in the back of his car and see a scattered assortment of junk lining the seats. I use this opportunity to give him a show. I put my knees on the seat and lean over the center console to clean his back seat. I can feel my short, tight dress riding up and my ass being exposed.

I hear him groan “fuck…” as his hands latch straight to my ass and he’s kissing and lightly biting the side of my right cheek. Read more »