Irish Ginger John

i don’t know if you know this about me, but I have a bit of a soft spot for gingers. Not as much as a certain best friend of mine, but a spot nonetheless. And you can’t really go wrong with an Irish accent. That brings us to Irish Ginger John. Not to be confused with Ginger Jon, who I may tell you about another day. 

IGJohn was a friend of a friend. Kind of. He knew a guy I knew. A guy who had a little, unrequited crush on me. I was at my regular spot one Saturday with some friends and ran into said guy I knew. His fiery haired friend was with him and it wasn’t long before his hands were on my ass. It may have been the ginger, it may have been the accent. It may have been the crisp summer air. Or it may have been the bottle of whiskey with which I had soaked my body from the inside out. I’m not sure, I’m not a scientist, ok? But I went home with him.  

It was pretty fun. He had a lot of energy. And he enjoyed having his anus played with. A lot. (Shortly after we arrived at his apartment, I received a text message from our mutual friend who told me I could call him after this guy disappointed me. I guess sleeping with one of his friends was not a big enough hint that I was not sexually interested.) He told me a great deal about his past and I suspect he is still in love with his ex wife. I don’t always sleep with men with baggage, but when I do, I end up as their bedmate therapist. At one point he seemed to be confused about what was coming out of his mouth and asked “why am I telling you all of this? I’ve never talked about this before.” What can I say? Drinking, combined with my trustworthy face make for all kinds of confessions. I keep most of them secret or anonymous, except for research purposes of course. Or if they turn out to be an asshole. As is the case here.

I think he may have made up some excuse to get me out of his apartment afterwards too. I don’t really remember. Whatever. I’m not really one who likes to stay and cuddle or go out for breakfast anyways.

I ran into this man a few weeks later at the same pub. He came with us to Denny’s after and proceeded to hit on my friend. I had not yet told her who he was, so she was briefly turned on by his charm. Briefly. Until I announced to the table that he and I had already fucked. Point, Amy. 

We leave and drop my friend off first, and he opens the door and steps one foot out the door as he asks her if he’s getting out there too. She says no. We drop him off next and he turns to me and says, “So are you coming in with me then?” I laugh hysterically and say, “Hell no!” What a fecking douche.

AC Pilot, Part 2

Read this before continuing on.

I haven’t spoken with the pilot for a couple months now, not since January 11th specifically. I would have written more about him sooner, but I was waiting to see what my decision on him was going to be and where things were going to go, and then I got annoyed with him and backed away and we just stopped talking. Let me take you through the last year with him.

He lives in Toronto and usually only flies into Regina every couple of months or so, sometimes more, but it’s not always an overnight trip. So after the first time he came over, I didn’t see him again until sometime in the late summer. We texted several times a week, he liked talking on the phone too, but I hate it. So every once in awhile I’d answer when he called, but most of the time I’d ignore it. Despite me telling him how I don’t want to talk on the phone, he would still try it. We talked about everything, including other men and women in our lives. It was nothing serious, although he would often wonder if I would date him if he lived in Regina or I lived in Toronto. My answer was always “maybe”. I would have considered it in the beginning, but we wouldn’t have been right for each other in the long run. He’s into some rather specific sexual fetishes, and I think he’s confused about his own sexuality. He experiences a lot of guilt regarding his desires. We had a lot of conversations about them, and I told him many many times that he is allowed to explore and want what he wants, as long as it’s not illegal and doesn’t hurt anyone.

I’ve told you about his fetish for women’s underwear and clothing. He liked knowing what I was wearing, but sometimes it was more so he could fantasize about wearing my dress, rather than imagining me in it. Or out of it. Prior to his visit in the summer, he would send me pictures of lingerie he was looking at online. It was usually Vanity Fair, either white, blue, or pink. He liked panties, bras, and slips. He kept saying how hot it would be to go shopping together and he’d buy me some to wear. And of course he talked about wearing them himself. I asked why he didn’t just buy himself some, or shop where he was. I’m sure there’s a much better selection of what he likes in Toronto. He could shop online, or go into a store and say he was shopping for his girlfriend. Hell, with the type of lingerie he likes, he could say he was shopping for his grandmother in the nursing home! But he was too embarrassed to do that. He did order a few things online, but as far as bringing anything with him, he would never do that. I told him to just put them in a gift bag and anyone checking his bag would assume he brought a gift for a woman. What’s the problem? Still too embarrassed. So, when he came through in the summer, I met him at his hotel and stopped at Sears on my way over. I bought us both a pair of pink satin panties, and stopped in the lobby ladies room to put mine on.

When he opened the door to his room, he was just as cute as I remembered. I could see why flight attendants of both sexes would flirt with him. He was a lot of fun to make out with. I liked kissing him, and I liked his hairy chest. Truth be told though, he could have used a bit of manscaping. Men, I cannot stress enough the importance of grooming around your penis. If the dentist congratulates me on the health of my teeth and I don’t even own dental floss, your hair is too long.

He loved the panties I was wearing. Literally could not stop touching them. He was very interested in the toys I have and asked that I bring one or two along with me. I brought a couple of my favourites and let him choose. Of course he chose the one that looked most like an actual dick. He kissed me up and down my body, trailing his hands along with his tongue. He had good hands that worked me inside and out. And then he wanted to use the toy. Before I got to have fun with it, he gave it a mini blowjob. (He liked to talk about his one fantasy where I could wear a strap on and make him give me a blowjob.) Then he fucked me with it. I don’t often orgasm when I’m with a man, but I did that day. I asked him if he wanted to wear the panties I’d bought for him. He said no, that was ok. I couldn’t believe it! I told him to get fucked and put on the goddamn ladies underwear I’d just bought for him! So he did. And I swear, he almost came just by putting them on. We started making out again, and let me tell you, it’s a little weird running your hands down a man’s body and feeling satin. It wasn’t bad though. Actually kind of nice. I mean, it’s soft, I like touching myself when I’m wearing nice lingerie, so it’s kind of the same thing. It didn’t turn me on, but it didn’t turn me off. It was just a new experience. He loved it though. When I finally pulled his dick out of his panties (I never thought that was something I’d be saying) and put my mouth on him, he was done in about a minute. I’d like to take credit for that, but granny panties did most of the heavy lifting there.

We did not have sex.

He left the next day and we continued our regular contact. I began to grow tired of our conversations. In matters of life, he would give me advice/lectures like my dad. If we talked about sex, it was always about his fantasies, and I was rarely the star. They got more intense as the weeks went on. I’ve had some great sexting with men in the past. Really great. Screenshot this for later kind of great. The pilot was not great at it. For starters, it was always about my ass. He’d fantasize about the big white panties I’d be wearing, pulling them down, and burying his tongue in my ass. I admit, it doesn’t sound that bad, but my kitty got awfully lonely in these fantasies. After awhile, my ass wasn’t even the understudy. It was all about his ass. He wanted me to order a strap-on for the next time he was in town and use it on him (He would pay for it). I had already told him several times I didn’t know if that was for me. And every time I engaged in conversation about it for curiosities sake, he took that to mean that I was starting to get turned on by the idea. Almost everything he liked, I really didn’t care one way or the other about. I wasn’t opposed to most of it, but it also wasn’t anything that got me revved up. I’ve licked and fingered an asshole or two in my day, and it’s not something I work into my own fantasies, BUT, in the moment, it can be pretty hot. Anything that you’re doing that gives another person so much pleasure is a turn-on. What really turned me off about doing it with the pilot was how much he talked about it, and tried to push it on me. It was the same with the lingerie. He would send me pictures of things he liked and ask which I liked better. I do not give a fuck what kind of panties you want to wear. I can’t imagine him finding any panties that I would think were sexy with a dick bulge.

Oh, I should mention the strap-on wasn’t anything that was new to him. He had been sleeping with a woman who loved using one on him. She was quite dominant. They probably could have had a very nice relationship with both their needs being fulfilled, but she was already married. And the things she wanted sexually, she had to step outside her marriage to find. The pilot worried he would never be able to find anyone who he would be able to share all his needs and wants with. He would go to these hottub parties and get fondled and blown by gay men. Sometimes there would be a woman thrown into the mix, but it was mostly men at these parties. And he would wonder what it was like to have a dick in his mouth and to perform oral sex on another man. He had a fantasy of having a threesome with me and another man. He wanted us to give the other man a blow job together and then watch me have sex with the other man. But he wasn’t gay or bisexual. *eyeroll* Ok man, whatever. Don’t label it, but don’t be afraid of it either. If you want to suck a dick, suck a dick. And finally, he did. But all these things he did, all these thoughts and fantasies he had, he felt so guilty about them. He started going to see a therapist about his “urges” and to try and fix them. Of course I told him that if the therapist agreed that he has a problem, he should find another one. But if they were actually helping him with acceptance, then great.

It was getting to the point that if he brought up sex, I just didn’t even want to continue the conversation. In November, right before my birthday, he offered to buy me a dress I wanted. It was gorgeous and expensive, and not at all in my budget. And he wanted to buy it for me. I said no. He tried to convince me to let him and I just couldn’t. It was not something that made me comfortable at all. At one point, he told me if we dated, I could have all his money. Everytime I went out, he would tell me how he wished he could be with me to watch me get dressed and be waiting for me when I got home. More than once he said he wanted to be my girlfriend. THAT turned me off. I like a sexually dominant male. I don’t want a girlfriend. And he knew that. He knew that’s why it would never work out between us in the long run. We might be able to have some fun here and there, but that would be it. And the fun in this whole situation was getting to be less and less. He was going to be in Regina after new year’s and we had plans to get together. But the closer we got, the more he kept asking about things. Like, was I going to bring the panties, was I going to get a strap-on, etc. Constantly. I got really annoyed, and he knew it. I was starting to make excuses for why I might not be able to meet up with him. I finally told him he was putting way too much pressure on me. Cross-country sex should be fun and exciting and freeing, not stressful. His flight got delayed in Winnipeg anyways, so it turned out to be a moot point. We didn’t talk much the week after that, and then nothing at all.

Yesterday was St Patrick’s Day and it reminded me of last year when I had first met him. I decided to send him a quick hello, see how he was doing. Right before we stopped talking, he had begun seeing a flight attendant with another airline. Maybe I should have left well-enough alone, but I hoped it would be a quick hello, how’s life, you doing ok, cool, ttyl. To start with, when I sent my message, his response was, “who is this?” Ouch. I didn’t respond. About a half hour later though, he sent another message saying, “Amy? Happy St Paddy’s to you too”. I said “Yep”. We had a brief conversation and I ended it with, “Well, I just wanted to say hi because I was thinking about you. I have to go meet a friend. Take care and have a great night”. He said the same and I breathed a sigh of relief. Until an hour later when he messaged me again. Asking about my night, why we stopped talking, etc. I said I hadn’t thought about it, and I was on my way to the pub, so, again, have a good night. He texted me again today. I should not have texted him yesterday. I should have let it die. But now, now I’m going to have to stick my dick in his ass. Sigh.

Men I’ve Never Met, But Made Me Cry, Part 3

Nick is recent. This past weekend recent. Nick is 26, tall, good looking (there’s a pattern here lol), smart, funny, educated, great job, owns his house, close to his family, sweet, kind. And the asshole who stood me up on Sunday night.

He messaged me on kik (a messaging app) over 3 weeks ago. I didn’t know who he was. He said we had chatted on pof awhile back and I had given him my username. Then he found me on pof and sent me a message there too.  Our conversation flowed easily right from the beginning. It started quite flirty, and I had initially placed him in the casual category, until I started to know more about him. I liked him. He felt the same way. He wasn’t really looking for anything beyond casual to start with, but within a few days told me it was obvious we’d be great in bed, but he hoped we had a connection beyond that. We talked every day, and were making plans for the weekend. Then he got sent to Edmonton for work. He develops and implements training packages and whoever was supposed to be doing it in Edmonton quit, so they sent him out there for 3 weeks. It actually worked out ok, because I was leaving for Cuba in a few days, and then would be at the farm the weekend after I got back, and then he would be back the weekend after. And that’s when we planned our date.

Even though we did some sexy messaging, he told me he has a 3 date rule when it comes to sex. But he might change it because we had been chatting so much. I told him no backsies! It was going to be at least 3 dates because I liked him. I don’t sleep with men I like right away. He told me I make him miss home. We talked about vacations and how he hasn’t taken one in over 2 years. He said he doesn’t need one because I’m his vacation. Fucking charming, right? Our conversations covered a lot of topics. He told me he trusts me, he’s never been this open with anyone and he could tell me anything. What he did was tell me everything I wanted to hear.

His flight got in late on Friday, and I had plans on Saturday, so we settled on Sunday for our first date. We were both looking forward to it. Or so I thought. I lost all interest in talking to other men. I turned down booty calls. I was getting invested in this guy. The last time we had contact was Saturday afternoon. He hasn’t responded to my messages since. And his pof profile is now deleted. I am sorely disappointed. It’s another bruise on my heart.

And now I’m suspicious because it’s exactly how Ryan stood me up. Twice. I’m in Groundhog Day, dating edition. I’m tired of fucking around, and I am becoming less and less amused by the encounters I have.

The only thing worse than a sad goodbye is no goodbye at all. 

Men I’ve Never Met, But Made Me Cry, Part 2

Scott. Scott happened in between my contact with Ryan. He was tall, handsome, 37, good job, funny, sweet, smart, interesting, charming, thoughtful. He travelled for work a lot though. He worked in the field of hazardous materials and had been all over Canada and the US to clean up various sites. He was in New Orleans after hurricane Katrina, he’d been to all kinds of accidents and there wasn’t much he hadn’t seen. He’s the guy that gets called when a site is too dangerous for anyone else to enter. He was in Alberta when we initially started talking, but Regina was his home base. We chatted almost every day. I wasn’t interested in talking to anyone else, I couldn’t wait for this man to have a break in his schedule so he could come home and we could meet.

Our conversations were rarely sexual, but they were flirty. He would ask me how my day was going, or message to say he was thinking about me. Then one day, we had this conversation….

S: You’re just the total package, hey?

A: Well, I don’t like to brag about it, but yeah, I’m a catch.

S: Well you’ve been caught, sweetheart!

A: It would appear so!

S: Far as I’m concerned, we’re a couple. So I tell everyone lol

A: haha You’re not really telling anyone that!

S: Nah, but I can’t wait until I can

A: Me too

S: I don’t mean to scare you, but I honestly think I’m starting to fall in love with you!

A: Really? How do you know?

S: lol I just feel it…hard to explain, I should have kept that to myself, sorry.

I don’t have all our texts anymore, so I’m going off the stuff I got screenshots of. I’m not exactly sure what was said next, but it was something along the lines of I was glad he told me and that I’m not going to say the same to him, but that he is someone I could see myself falling in love with and I do have feelings for him. He told me that was enough for him. And then:

A: I’m a…realistic romantic shall we say lol We haven’t met yet, so it’s always in the back of my mind that it might not be real.

S: I know, and that’s why I think I’m fucked up with the way I feel about you, but I like it and think you’re the most amazing person ever! Haven’t found a flaw in you.

A: Oh I have them! Do you fall hard and fast in relationships?

S: Perfectly imperfect.

And now from memory again. He does not fall hard and fast, and did not expect to find someone like me on a dating site. It’s taken him by surprise. He asked what my flaws are, and every one I came up with, he found a way to put positive spin on it. It was a bit of an intense conversation for me. I’m glad it wasn’t in person because I don’t know if I could have kept my composure. It made me anxious and excited and emotional. I started tearing up. The way this man made me feel is a feeling I’ve been craving ever since that night.

The next day was the last day we spoke. It was brief, just a couple of texts. I went out that night and when I messaged him the next day, I got no response. I tried a couple more times, and sent him a message a couple of weeks after on his birthday. Nothing. I already felt a little unsure of my feelings because I hadn’t even met him yet, but I allowed myself to be hopeful. And now he was gone and I felt like a fool. Even now, all these months later, writing about it makes me sad. I’ve always wondered about people who fall in love online before they’ve even met each other. I don’t wonder anymore.

What I do wonder about is what the fuck is wrong with this guy?! Did he scare himself off? He’s still on pof, but often doesn’t have his pictures public, and his city has changed. He was in Montreal last time I checked.

“The biggest coward is a man who awakens a woman’s love with no intention of loving her.”

Bob Marley

Men I’ve Never Met, But Made Me Cry Part 1

The next 3 posts are not fun sex stories, but it’s important to me to write about the bad, along with the good, even though remembering it really sucks.

In the fall, I started talking to Ryan. He was tall, cute, 26, great job, owned his own house, funny , smart, confident, flirty, sweet, all the things I look for. We had really great conversations, and then he just disappeared. He didn’t respond to my messages, and he deleted his profile from POF. Oh well. We had only chatted for a week or so, maybe a bit longer. It’s not like I had fallen in love.

He messaged me again at the end of November, beginning of December. He had a new profile on pof and asked if I remembered him. Obviously. I asked what the fuck happened to him and why he dropped off the face of the earth. He told me his work sent him to Edmonton or Calgary (I don’t remember) for a couple of months. He worked in IT. He apologized for disappearing and said he didn’t think it was fair to start anything with someone when he was going to be gone for so long. I accepted his apology and told him not to do it again, to just let me know if something happened in his life. My plan was to keep it casual with him though, a guy who does that doesn’t get anything more than sex with me. So we flirted and would send sexy messages. We were flirting the first night the 20 year old came over. Actually, when lil Jon showed up and rang my doorbell, I didn’t get up to answer it because I was talking with Ryan and had just invited him to come over. By this time Ryan and I had been chatting for just over a week. His response was that he didn’t want this just to be about sex. He wanted to actually get to know me and take me on a date before anything physical happened. Aww. I told him that was really sweet and I was ok with that. And then I got up to let the 20 year old in.

Ryan and I kept having great conversations. My plan to keep things casual was failing with every conversation we had. He was winning me over with his charm. We had set up a date for a Friday night. I had other plans that evening also, so the plan was him to pick me up when I was finished and we’d go grab a late drink. Our last contact was around 5pm that day and he told me how much he was looking forward to finally meeting me in person and to just message when I was done and he’d come get me. I messaged him about 9 to let him know I was on my way home to freshen up and would be ready by 930ish. No response. I get home and get ready, still nothing so I message again. Nothing. I washed off the makeup I’d put on and took my carefully selected dress off and hung it back in the closet. I’d been stood up. And wouldn’t you know it, his pof profile was deleted again. If you’re keeping track, the same man stood me up the same way 2 times. 2 times! I was sad about it. The little fucker made me feel feelings I hadn’t wanted to feel, and then abandoned me without a word.

Jump to January a few weeks later and he messaged me again! This time, he started the conversation with “Hi, remember me you dirty girl?” “Oh, is this the Ryan who stood me up and disappeared for the second time? Yeah, I remember you.” “I used you like the slut you are. I still have all the pics you sent me, great jerk off material.” “Why are you being a jerk now?” “Because that’s what you want.” “No, it isn’t.” “To be treated like a filthy slut. You like it, admit it.” It was at this point that I blocked him and cried a little. I didn’t and still don’t understand why he was so sweet before, and then decided it was ok to speak to me like that. Asshole. Oh, if you’re wondering what kind of pictures I sent him, well, I look pretty sexy in lingerie. I have never sent a picture that I would be embarrassed by if it was not kept private. I’d be pissed for sure, but not embarrassed.

The Cuban

I recently took a winter holiday to Cuba. It was beautiful! I highly recommend it. It seems everyone expects me to have some adventures when I go away, and by adventures, I mean sex. I recently came across a term I think perfectly describes my sex life up to this point and how I approach it. “Sport fucking”

I do it for fun, when I want, with who I want. Cuba was no exception. Our first night at the disco, I met Alex. He is a security guard at the resort we stayed at and sooo cute. My memories are slightly foggy, but I remember dancing and drinking and having a great time. And then I was introduced to Alex and the next thing I know, the disco is quiet and dark and I’m in a corner with his dick in my mouth. The silence was broken by the sound of his balls slapping me as me bent me over a table. From there, we moved to the beach. He didn’t speak much english, but he understood me when I asked, “Can we have sex on the beach?” Don’t worry, we used a chair, I didn’t have to douche any sand out of my vag after. From there, he took me to a random, unoccupied hotel room where we continued our path of carnal carnage. He walked me back to my room and we said goodnight. I’m told when I got in the room, I serenaded my friends with my rendition of Spice Girls “Wannabe”. You can imagine how great that was. My friend had been starting to worry about me, and had sent me a text, but my phone was in the room, so that wasn’t helpful. She was even about to come looking for me, but she never would have found me.

The next day, I couldn’t remember his name or even his face. Every time we passed a security guard, the girls would ask if that was him. I’d look and say, “No” or “I don’t think so”. Real classy. But when I saw did see him, it was just in passing, and he did look vaguely familiar, so I had a feeling I had found him. On our last night, we went to a nightclub on the island called The Cave. It was cool, but I wouldn’t do it again. It is literally a bat cave. An old one. You have to walk down this spiral staircase into it. It wasn’t as claustrophobic as I thought. It’s a little low in places, and there were vines hanging everywhere, but there were big holes in the top so you could see the sky and air could get in. On the bus ride back, someone (me) suggested skinny dipping in the pool. So we get back and strip down and jump in! There was a security guard there at the time, and not surprisingly, he was perfectly fine with 7 or 8 women getting naked in front of him 😉

My security guard showed up and started chatting with me from the edge of the pool. I asked him if we had met before and he said yes. I asked if we met in the disco. Yes. Did we meet on the beach? No. What? That was my friend. Oh, well where is he? He’s coming here in about 20 minutes. Oh ok, I’ll wait. Tell him to hurry. A few minutes go by and I ask him where his friend is and he says, “There is no friend. You really don’t remember me?” I laugh and say I was pretty drunk and I thought it was him and to stop messing with me. Then I told him to prove it was actually him and to tell me all the places we “met”. He passed the test so I told him to get in the pool, and he did. He said we should meet on the beach. I said, “Later. Can we have sex in the pool?” “Yes”. hahaha So we start making out and then he sees one of my friends is still in the pool. So I swim over to her and tell her I’m going to have sex in the pool. She’s cool with it and swam to the other side to enjoy the Cuban sky. I go back to Alex and he’s like, your friend is still here. And I’m like, So? And he’s like, Ok. Sex in a pool is not all it’s cracked up to be. I mean, it was fun, but it’s not going to be my first choice unless I have a good silicone lube with me. (Silicone will stand up to any water sex you may have. Showers, pools, etc) From there we decided to meet on the beach again.

I dropped my stuff off in the hotel room and took a walk to the beach in my towel. Alex wasn’t there yet, but the sun was coming up and it looked so beautiful, I couldn’t resist dropping the towel and taking a run into the ocean. It was amazing! But Alex didn’t show up. I wandered around the resort and ran into some ladies I’d made friends with who hadn’t made it to bed yet either. And then I saw him. I called out his name and he came over to me. There was a guy watching us and he tells me that’s his boss watching. Whoops lol I tell him I’m going to bed and start back to the room. I meet him around the corner and he tells me again that was his boss and he has to get back to work. I got him in trouble. haha I tell him I’m leaving that day, so, bye forever! And then I went to bed.

That was my sexy Cuban story.