Wherein I make the next move and uncover what’s in his pants.

With the early morning text exchange with Lewis, I felt optimism. A nice feeling, for a change. He was flirty and sexy without being crass. I liked it.

We texted off and on throughout the day, sharing some jokes along the way. I’d been busy at work with the new role – finally – and it helped me to not worry about whether a few hours had passed without my hearing from him.

Our first date was Monday night. Through Wednesday morning, we exchanged relatively steady, if infrequent, text messages. He wasn’t as consistent as the school teacher, but he’s definitely not a bad texter.

I started to realize my schedule was conspiring against me.ย I also started to wonder whether he was going to ask me out again.

It’s funny; normally I’m pretty bold in my dealings with people – if I want or need something, I ask for it. But I’ve become hyper aware of the fact that men seem to say yes when you ask them out, even if they aren’t too keen. I’ve pushed dating along with some men that the moment I stop texting, all communication stops. Therefore I tend to not ask because it means if they ask, I know they’re interested. If they don’t text me back, I don’t text them again because I assume if they want to, they will get in touch.

I espouse this philosophy all the time – if he likes you, he will reach out. I do believe it’s true. But I am hard pressed to think of ANY other situation in my life that I approach in the same way.

I wanted to ask Lewis out. Wanted to ask him if he’d like to come over to my place for a drink. I know he’s busy with work and he has his child almost 50% of the time, so I wasn’t taking his lack of asking as any big deal – it hadn’t been more than two days. His texts to me were far more than just keeping me on the back burner.

So I took the plunge and did it – even starting my text saying “can I be so bold as to ask you…”.

He said he would love to see me but he had his daughter on Thursday. So I asked if he was free Wednesday instead – it was, and the timing worked perfectly. He would be getting home from work around the time I would be ready to see him.

I’ve been conditioned for men to be late, or cancel at the last minute. If Tony said he’d be over at 8, I expected him at 9:30. So I was surprised when Lewis texted me that he was at my door, right on time.

He greeted me with kisses on either cheek. We went to my kitchen and he decided to have what I was having – proscecco with two liqueurs – also known as the first cocktail I had on my first date with Tony. Drinks in hand, we moved to the couch, where we talked for 90 minutes. It was probably 45 minutes before he put his hand on my leg. Point being, he wasn’t immediately all over me. I even caught myself wondering why – and had to check that attitude right away, as a respectful good pace is way better.

When I went to the kitchen to get a refill, he followed me in. We moved to dark ‘n stormy’s, another favorite. As I was messing about getting the drinks, he came over to me, put his hand around my waist, and pulled me to him.

If the kiss in the rain was steamy, this kiss was just plain hot. We were immediately all over each other – his mouth crushing mine, tongues finding each other again, hands everywhere. He had his hands on my ass, or in my hair, or on the back of my neck. We would break apart for a second and then dive right back in. At one point he put a hand down the front of my pants and I stopped him, telling him I was menstruating.

We must have kissed for at least 15 minutes non stop – I was literally sweating.

I pulled back from him ever so slightly and said “I think there’s something I need to tell you. I’m not vanilla”.

He said “what do you mean?”

I said “sexually, I’m kind of kinky. I’m experimenting and learning my boundaries and haven’t found many. I like it rough. I’m kind of submissive. And I have been told I’m insatiable – and while I can be satisfied, I like sex A LOT.”

I waited, wondering what he was going to say. He broke into a broad smile, looking down at me, and he said “Oh Ann, we are going to get along just great.” And with that, he pulled me into him. He removed my shirt and my bra and put his mouth on one nipple, than the next. I arched and moaned against him. He held me up as I lost my footing from pleasure.

I needed to not be standing. We moved back to the couch, where he took off his dress shirt and undershirt and my eyes likely widened as I took in his perfectly sculpted chest and arms. I’m a sucker for big biceps and forearms and he has an amazing body.

He sat down on my couch, topless, and I straddled him and he took my breasts back into his mouth.

I slipped my hand between his legs. He moaned. I could feel him getting harder with my touch. We kissed and I put my hands behind his neck and I ground myself into him. We moved together like we’d been dance partners for years. The dude can move.

We stopped and he held my face in his hands and said “Ann Ann Ann…there are going to be FIREWORKS.”

At some point we discussed when we could see each other again. Next day I was free was Tuesday, so it became a date.

I dropped to my knees in front of him on the couch, between his legs. I explored his chest and stomach with my mouth and lips, taking my time to kiss him everywhere, then running my tongue along the waistline of his pants, all the while rubbing his cock.

I needed to see it. He undid his belt and I unzipped his pants, putting my hand into his underwear to pull it out and thought




In my hands was an uncut cock, not even fully hard, and it was the biggest I’d ever seen (and please don’t ask me exactly how large; I don’t know. My guess would be 9″ long when fully erect but it’s not like I asked or measured). After taking a second to absorb what I was holding, I had him in my mouth. He groaned in pleasure; I could barely get my mouth around him.

Then he got hard. I couldn’t believe my eyes or my hands, which had trouble encircling his girth.

I told him it was gorgeous, and meant it.

I did not make him cum, nor did I try to. I played with him, and him with my breasts, and as we talked he slapped his gigantic cock against my chest while making appreciative noises.

He said “I’ve never before wished the weekend could be over and Tuesday would come.” He asked me which positions made me cum and I told him I liked it from behind, or on top, then giggled while saying I liked it on my back with my hands on a man’s shoulders SO HE COULD BE DEEPER. I said I didn’t think that was going to be an issue with him.

I cannot even begin to accurately describe how crazily instantly excited and wet I was at the thought of taking that man’s cock. And even better: I think he’s almost as excited to be with me.

But I have to wait 6 days to get it. Feels like a dating lifetime; will we survive?

79 thoughts on “Wherein I make the next move and uncover what’s in his pants.

  1. I too will say yes if you ask me out.
    Hey Ann, so I just returned to having internet and in a period of 10 days some new people have added themselves to my crazy blog and one of them, well I think is down your road. Hereยดs the link, talk about kinky….this is right out porn. Good thing though, This way I donยดt get into strange webs that can give me a virus into the computer ๐Ÿ˜‰ Kidding, i donยดt see those things….
    Link ! https://bettersexforum.wordpress.com/ Enjoy!

      • Nope, just sight seeing would be better said, and the photography I wouldnยดt call it very professional but can you tell me what in the world was those things hanging from those black dudes?
        I like better the reading and the sensuality of some poems-stories, for sex I too have my share in the real world. I just found it funny that a porn blog would actually be in wordpress and even funnier that they are following me

    • I certainly hope so. I said to a friend last night that even if he seems less interested or not the right one, I’m still going to do everything in my power to have sex with him at least once!

  2. I say good for you!
    I too was given a 5 day waiting period, but in my case it’s not sweet anticipation and I do wonder whether I’ll actually survive (I know I will, but it sure doesn’t feel that way!).
    So enjoy your building anticipation, not much that can go wrong with that!

    • It can go wrong…it’s online dating after all. People all talking to multiple others, and all that. And I’m learning when I like someone, or at least see the potential, it’s harder to me to chill and accept when I see them online, etc.

      • Well, anything can go wrong! Look at me ๐Ÿ˜‰
        But we need to keep the hope alive that things will go for the best ๐Ÿ™‚
        Well… if you saw him online, it means that you were too, so… ๐Ÿ˜‰

        • Yes, exactly. But I have ignored all of the “so and so wants to meet you” messages as well as almost all of the new messages in my inbox – except those from one guy who – of course – was someone I went on one date with and then he told me he wasn’t interested.

          • Well, do you *know* that he did more than that? Maybe that’s all he went online to do ๐Ÿ™‚
            (I mean, obviously, I have no idea how these sites work, so maybe you do know ๐Ÿ™‚ )

          • Nope, I have no idea. I just translate all of this into equalling rejection. It’s not anything he’s done or not done, really, other than not sending me a good morning text ๐Ÿ™‚

  3. Not that was a hot story you tease! You had him in your mouth but left him full…haha! Poor guy! His poor blue balls must have been aching! And your 23 days must seem like a year. In any event, I am very happy to hear you found a nice match…fingers crossed for you.

    • My fingers are crossed as well. I’ve learned some things about myself and my ability to just relax about things when there is a man that I see potential with. It’s WAY harder for me.

      With regard to leaving him in that situation…I suppose I could have done that, but I wanted to wait to go further. It was really damn hot as it was. And he said he was going to go home and fantasize about me while he finished himself off. I thought that was hot ๐Ÿ™‚

      • The ability to relax and not rush things is huge. I think people as a society rush everything. Some things need patience and time, especially when you want something more meaningful…the end result is usually so much better! And yes, it was very hot…

        • I’m not sure I can explain it well (or perhaps this is just me trying to justify things) but I am not rushing a relationship, per se. I know 100% that I need to learn and experience a lot more with someone before I know they are right for me. But I also know when there is more potential for that.

          I would respond badly to someone who immediately says “Oh I want you to be my girlfriend”… it’s happened to me and I think they are foolish.

          I guess I have trouble with reconciling feeling like there is one person who has way more potential than the others, but continuing to engage with those others. That’s what feels odd to me. And odd to be on the receiving end as well.

          • I think your doing a good job of explaining, but of course some things need clarification. Can you rephrase this sentence…”I guess I have trouble with reconciling feeling like there is one person who has way more potential than the others, but continuing to engage with those others.”

          • Missed a word in that sentence!! I have a hard time engaging with other people when one person stands above. For me, I like to then focus on that person and figure out whether they are the right person for me. Then move on if they aren’t.

            So I put that on other people as well. I say – how is it possible if they really like me, that they could continue to engage with others? And therefore if they are still engaging with others, how much could they really like me?

            Even when it’s just a possibility of something. I’m not getting ahead of myself assuming someone is the right person for me. But I like to be able to focus.

          • Yes, I can understand that. Though, being where I am, I think that I can see great potential with someone and still consider others ‘for fun’… but of course, I don’t have the same exclusivity expectations in a relationship as you ๐Ÿ˜‰

          • Well… I’m not sure ๐Ÿ˜‰
            But I think you attach more importance to the fact that they don’t play without you than I do!

          • Well I know I don’t want an open relationship. If I’m in a relationship with someone (as in, they are my boyfriend), the only thing I’d consider is us playing with others on occasion. As long as we are together.

          • See, I don’t put a label on it, I just go with the flow. If he needs to know he can go and have fun with other women, I don’t have a problem with that. It was quite nice to know that I could play with others without guilt. Though I agree, there isn’t a label as to BF/GF either ๐Ÿ™‚
            As I said, I don’t need that part of the relationship as much as you do ๐Ÿ™‚

          • Yup, that’s exactly it. And it’s all a theory for me right now. I just know that I don’t want to end up in the same kind of sexless relationship I had before. I still want to explore things, but I very much want to do it in a committed relationship, if I can.

          • That’s the thing we’ve always liked about swinging is that you can be honest with each other and not get wigged out when one of you gets their lights drilled out.

    • He is lovely and one of the few men I’ve met where I feel we are well matched on pretty much all levels.

      The downside of that is it’s been hard to not want more communication and to be chill about everything. My natural inclination is to assume that him remaining on the dating site / not texting constantly means he’s not interested.

      I really hope that fairy returns.

      • Baby steps! I like the chemistry between you too. And you said something which I’ve always noticed: when you find the right partner, it is like a dance. The fact that you described it like that from the get go seems very promising!!

        • Yes. I liked the chemistry too. It’s mental and physical – and I think emotional as well, but that’s a harder one to gauge. His profile clearly states he’s looking for a relationship.

          But boy, the way we moved together on that couch. Simulated sex. Yowza!

      • I know what you mean. We introduced a couple into the lifestyle and took them to their first house party. We asked them to party and went back to a bedroom. Wifey unzipped his pants and out popped this huge dick. I’m reasonably large but this guy was probably 10-12 inches, no shit. Within two seconds wifey was on her knees trying to swallow the whole thing. That was a shock to me as she’s never like that with a guy, girls are different but guys no. His wife and I stood there and watched her suck him off right off the bat. Then we climbed in bed and she got him off 3 more times. She says if the truth were known, he’s not that great a fuck but she loves the size. Of course she might just be trying to not hurt my feelings. LOL

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  5. Gulps! I’ve actually had to turn two guys down for being overly blessed with the cock fairy! Had I known, I would have sent them your way. ๐Ÿ˜‰

  6. I said โ€œsexually, Iโ€™m kind of kinky. Iโ€™m experimenting and learning my boundaries and havenโ€™t found many. I like it rough. Iโ€™m kind of submissive. And I have been told Iโ€™m insatiable โ€“ and while I can be satisfied, I like sex A LOT.โ€

    Ann in a nutshell?
    Love it!

    Hope you survive the coming onslaught, Ann!

    • Oooohhhh Lucy I’m glad you liked it!!

      The grinding reminded me of ages long past when I really wanted to have sex with someone but couldn’t… it’s like trying to feel what it’s like without doing it. It was fun. And hot.

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