The Jamaican

bad sex

Last night, the Jamaican man I had met at a swinger party once, while I was with the Professor, came up here to see me.  He drove 2 ½ hours and got a hotel.  In case you aren’t following the story, we had been flirting a bit at the party, via eye contact, but never hooked up.  According to the Jamaican he was upset about the Professor appearing not to want to share me at the party.

I hadn’t heard from or seen him since, until he found me the other day on Plenty of Fish.  Since then we’ve been texting and he’s called several times and seemed very interested in getting together.  It cracked me up because yesterday, before he drove up this way, he called me his “lover girl”.  Has he been reading my blog?  LMAO

In any case, this guy is a Nurse Practitioner that is not a doctor “yet”.  He is 6’6” and 265 lbs, muscular, dark skinned and nice looking with a sexy Jamaican accent.  He says he moved to the U.S.  a little over a decade ago.  He was married for a long time and has only been divorced about a year. 

The reason he joined the swinger site, according to him, was because he was seeing a woman up here occasionally and they decided they weren’t going to work out as a couple but would be good friends with some benefits.  She found out about the swinger scene here from a friend at work and called him all excited about trying it out. 

Since then he’s been to a few parties and also played with a couple of married women but he says he is losing interest in the whole scene, that it isn’t something he can see himself doing with someone he is in love with.  He does play with the wife of a guy down where he lives but he says it is a bit awkward with the guy there watching.

Anyhow, one of the guys at the party we both attended had really talked up the Jamaican’s cock size, lol.  He was going on about how he was just huge and had I seen it and it was “this thick” and was trying to find pics on the swinger site on his phone to show me.  At the time the Professor hadn’t seemed too thrilled about this conversation.  I think the guy claimed he was like 10 inches too.

Now that I’ve seen it up close and personal I’d say the length was an exaggeration.  He WAS very thick but not totally unmanageable or anything (which is good, lol).  He was also probably closer to the 7.5-8 inch range than ten inches. 

I was able to get my mouth around him well enough to give an okay blow job, I think.  Still, he was uncircumcised, which I am not used to.  I’ve only been with one other guy who was not circumcised and it was a long time ago.  I wasn’t quite sure what to do with the foreskin.  Like, should I pull it back and suck on it that way?  Or would it feel good at all to him to actually suck around it?  So I tried a little bit of both, lol. 

Back to the beginning though, he kissed me when I first walked in and I was disappointed to find I really didn’t much like his style of kissing.  He wanted to stick his tongue in my mouth and just hold it still, or suck on my tongue and bite it and bite on my lips.  Bleah.  I’m not much into kissing unless I’m really into a guy anyway, so it was like doubly weird.  I was hoping this didn’t mean he was bad in bed.

We kissed and then spent quite a bit of time talking.  The air conditioner wasn’t working in the hotel room so he had called down to the front desk and we were waiting for them to come up and fix it.  He was actually really interesting to talk to and nice and easy to get along with.  I just love his accent and hearing about Jamaica too.  He says like 90% of the people there have no jobs and that he grew up in a family with 12 kids and they are all tall like him.  Even his sisters are over 6 feet tall and some of his brothers are taller than he is. 

So, since the people still hadn’t shown up after like an hour, we went ahead and got down to it.  More of the odd kissing and then he started sucking on my boobs and I gave him a blowjob.  After that he went down on me, which felt really good and he was doing a great job but he didn’t do it long enough for me to be able to cum. 

He said he has had a vasectomy and doesn’t play with very many people so I agreed to let him go without a condom.  Maybe some would see that as reckless but in his case I feel fairly safe.  He doesn’t strike me as the wild or dishonest type at all. 

In any case, the actual sex was over in like under 3 minutes, lol.  :p  Now I know why, when he asked about seeing the videos of me and the Professor he was shocked when I said they were over an hour each and we might not have time to watch them.  Basically, he got on top of me and pumped away until he came.  I was just starting to feel good when he stopped and came inside me. 

He apologized for cumming so quickly and asked me if I came. I didn’t want to lie so I said no.  We both cleaned up a bit and then the woman from the front desk knocked at the door.

I jumped up to get dressed and he pulled on his shorts but was telling me I should just lie there in the bed with the covers over me.  I really didn’t want to be doing that when this lady came in the room, lol.  He couldn’t understand why…

So she came in and because he had to tell her to wait a minute while we got dressed anyway I think it was pretty obvious we had just been having sex, haha.  She was trying to contain a smile while she checked the air conditioner.  It still wouldn’t work so we ended up having to move next door.

In there we talked for a long time before he got on top of me again for more sex.  He asked me what would make me cum and I really didn’t know how to respond.  I hate it when guys ask me stuff like that during the act! It’s like, what would make me cum is him already knowing what to do, without having to ask because that totally turns me off. 

So he asked me what position I would like to do and I said maybe doggystyle.  We did that for a while and he asked if I would like to ride him so I did.  I really wasn’t feeling the chemistry with him and was kinda hoping the second time wouldn’t be too long either.  It was longer though and he had me lie on my back again with my legs up and it did feel good for a bit.  I never did cum though.  Thankfully he didn’t ask this time, after he again came inside me. He was one of those guys that if I started to get excited or make noise he’d ask if I was okay.  Sigh…

So after the second time he rolled onto his back and started snoring, LOUDLY.  At first he woke up for a sec and apologized for snoring and pulled me over to lay my head on his chest and went right back to even louder snoring, haha.  I managed to escape his sleep grip after a while and got up and brushed my teeth and stuff before coming back to bed and sleeping on my own side.

I was lying there and couldn’t stop thinking about the Professor.  I miss him terribly.  Sometimes I wonder if I even want to play with anyone else at all.  I had to drive past his apartment complex in the morning on the way to get my kids and I think I may have seen him driving past on the other side of the road on his way to work.  I don’t know if he saw me.

The Jamaican wanted to spoon with me in the morning and I was lying there wanting to cry.  I didn’t really want to be lying there with someone other than the Prof.  I also never showed him the videos he had asked about, partly because it would have hurt to watch them and also because I didn’t really feel like sharing that with anyone.  It’s probably a good thing because if he saw me orgasm a million times during sex with the Prof it might have made him feel pretty bad!

When I left the Jamaican said he was going to miss me.  He had also mentioned the night before that sometime he would love to have my kids and I down to his place.  He has a big house with a swimming pool and said we could have fun there.  The girl he plays with off the swinger site has been trying to get him to have a swinger party at his house but he was saying he wasn’t sure he could handle people having sex in the pool and then watching his kids play in it a couple days later without worrying about germs. 

Anyhow, he says he will call me later.  I don’t want to hurt his feelings because he really is a nice person and I enjoyed talking with him but not really excited about the sex.  I’m not saying I could never do it again but don’t want to lead him on to think I want a relationship or anything either.  Thankfully I have the excuse that I don’t often have Monday nights free and my ex normally doesn’t take the kids overnight so most times I can be “unavailable” for getting together. :p

21 thoughts on “The Jamaican

    • Thanks. :/ I miss the Prof. so badly. Even when we were still talking I felt that way sometimes after sleeping with someone else, but now, without having spoken to him for 16 days (yes, I’m counting) it’s especially hard. Getting under other guys isn’t helping me get over him much yet.

  1. Aww shucks. What a pity. I also hate when guys ask a) if you came (if you have to ask then NO), and b) what they can do to make you come. Totally agree that it’s knowing what to do without asking that does it! Dr Fathead had the magic touch and the magic knowledge (from fucking around, probably but whatever) and nobody has come (excuse the pun) anywhere close since! Dammit.

    • I know. Asking if I came is annoying too. You would know, believe me! Haha Yeah the guys that have been able to get me there pretty much all learned by fucking around a lot. I guess it takes that to get that magic touch.

  2. Bummer. I did notice something you said that had my eyebrows crawling up my forehead, though – he asked you what would make you cum and not only couldn’t you tell him, but it turned you off along with you assuming that he knew how to do that. My question is why would you assume that he’d know that? I’ve said this a few times in some of my blogs: I know how to make love… but what I don’t know is how to make love to YOU.

    I ain’t really trying to tell you how to handle your business but I just don’t know how you – or any woman – can expect a man to know how to make you cum (or know how long that might take or if it’ll even happen at all) the first time you have sex with him – although, admittedly, some guys know how to figure this out and it’s not an easy thing to do because you’re working with just basic information and, well, it takes time to learn the specifics.

    I am sorry you were disappointed, though – better luck next time.

    • Kdaddy! I was hoping you’d have some advice on giving blow jobs to uncircumcised men, lol.

      What am I supposed to do when a guy asks me that, while he’s inside me and lying on top of me? Sit there and give him a lecture on sex and the intricacies of female desire? At that point there was NOTHING he could do to turn me on because he’d lost me by having to ask!

      What turns me on is a guy that can dominate me, having to teach him anything is an instant turn off. The married guy, the Professor, they can make me cum because they know how to take control and it’s losing control that brings me to orgasm. I am very submissive and just can’t get off on being the one that has to do the teaching at all. This is why I suck at being a cougar and mostly prefer men that are close to my age or older.

      There is nothing technical that he could do that would make me cum without the domination and already knowing what to do. How can I explain to a guy how to work his dick? LOL That is something he’s gotta figure out by trying different stuff on me. Also, a big part of what gets me going is being in a “sex trance” and it gets broken when someone interrupts my focus with questions.

      • You handle uncut guys by peeling the foreskin back and using a hand to keep the head exposed unless he’s one of those guys whose knob is fully exposed once he’s fully erect. You can let the skin retract – and then use your tongue on the inside of his foreskin in the same way a guy will use (or should use) his tongue to get at your clit under its hood.

        See, I would have asked you that important question before the fact (but that’s me) and if you couldn’t answer it then, it would tell me that I might have to bring my whole bag of dirty tricks… that’s not necessarily a bad thing. You know you like the man to kinda dominate you and just take you… but he didn’t know that, did he?

        Some of us learn that if we come on too strong in bed, some women tend to freak the hell out so, by default, we don’t do it. I do wonder, all late and wrong, of course, if your experience with him would have been better if he’d known what you just told me?

        I’ve always thought it was really messed up for a woman to know how she wants to be done – and then assume that a guy she’s screwing for the first time SHOULD know this already. Then again, because of this, it makes me behave the way I do in this situation: Do it all until you do something she doesn’t like. Sometimes, OJT is fun for us… and not so much.

        I’m not blaming anyone in this – it happens more often than not; I’m just pointing something out to you from a man’s point of view. I know I can either be as meek as a lamb in bed… or someone’s worst nightmare and the decision to slip into whatever mode is required is based on my knowing, ahead of time, what will turn you out. So if you told me (and you have) that you like to be dominated and made to lose control, oh, well, hang on to your ass.

        But,sadly, this is just me and not all men approach ‘uninformed’ sex this way because, as I said, we usually get our heads handed to us because we can’t do something she thinks we should know already – we’re not mind-readers, sweetie.

        I know I wouldn’t have asked in the middle of the deal but, yeah, you could have told him how to work his dick in whatever way you knew it was going to please you; shit, I’ve had women do that and it has never bummed me out because if you don’t tell me, how am I supposed to know? What I do know for a fact that what works with one woman might not work on another woman, just like I know, for instance, the stuff that makes my baby orgasmically insane might work today… but it won’t work tomorrow – and I know how to flip her switch.

        That doesn’t stop her from telling me what she wants in that particular moment; once she does, it’s now my job to deliver (or else). I know – and because she told me before the first time we fucked – that she’s not fond of ‘gentle’ sex so I knew that when we got around to making love, fucking, screwing, whatever you wanna call it, I’d have to get into “do her in” mode and, whatdya know, she liked it!

        So, let’s say that I know every sexual technique and position possible… how am I supposed to know what’s gonna work on you if (a) I don’t ask and (b) you don’t know or can’t – or won’t – tell me? Leaving a man or a woman to their own devices is not always a good thing as you have now discovered.

      • I was wondering about the foreskin thing because some people claim that boys should be left intact and that gives them “more feeling” later on when they are having sex. If you have to pull back the foreskin anyway it doesn’t seem it would matter. Guess I’ve seen a few too many circumcision debates back when my boys were little. So I was wondering if you were also supposed to give some sort of attention to the foreskin, lol.

        No, he wouldn’t necessarily know I wanted him to dominate me, but telling him “hey, you need to dominate me” kind of defeats the purpose because that puts ME in control and is a turn off. He was, in my opinion, way too gentle so yeah it may have helped to ask before we ever got naked. Also, if I started to make noise or act excited he’d stop to ask if I was okay, which of course made me feel a lot more inhibited and again ruined the feeling.

        See, I kinda WANT a guy to try out everything he knows on me, lol. The variety makes it more fun and that way we can both discover how we click together. That’s the best way to go about it, rather than asking me to explain stuff to him. I don’t have a clue how to tell a guy to work his dick since I don’t have one…maybe if I had some sort of diagram and could tell him what areas to hit but come on, lol.

        The way I see it is that if he doesn’t know what to do or is inexperienced, he’s probably not a good match for me. Plus I don’t want him to not try things on me that he has tried on other women. Who knows, I might like it. I want the whole bag of tricks. Telling him I like it one way may not cut it tomorrow because I’d get bored with the same old thing all the time.

      • But, sweetie, if you don’t let a guy know that, what’s he supposed to do – guess? We have a very high failure rate when we have to guess!

        I feel a blog coming on…

  3. And you just assume that he knows he’s supposed to do that. Incredible… simply incredible. He was supposed to do something he didn’t know he should be doing. See, before you told me what you told me in your comments – not that I’d ever get to use them, mind you – but I would, by default, bring my biggest bag of tricks for that first time; it’s just that all of us don’t know that we should be doing this because we learn that it doesn’t always work when we do.

    • See, but some guys do know to do that and it generally comes with experience, hence my preference for sexually experienced men. I’d guess that if you try all your tricks something is bound to work eventually, lol. I mean I don’t sit there and say “what do you want me to do” either. I start doing whatever and watch his reaction. If he likes something else or doesn’t like what I am doing, I guess I will find out!

      • Uh-huh, some guys do know… but not all of us do. You just got my attention with something that makes me – and a lot of guys – totally insane… or gives us more of a reason to question a woman’s sanity! But I do, in all seriousness, hope your next encounter works out a little better.

        And in response to Pervertically, yeah, I know – most women I’ve run into are like that; I don’t know about it being organic but I do know that do anything other than that is something that bothers women even though we, as men, know that women are some really complicated creatures…

  4. oh man, that was not a very exciting night, was it?

    I add to the hating of the 1) “did you cum?”, and 2) “what makes you cum?” questions too. In regard to 2) (and in response to kdaddy) – I prefer people trying to find out what makes me tick by trying things out rather than asking. it’s just much more organic and less awkward… sure, sometimes verbal communication is necessary, but there are many more organic ways to explore one’s likes and dislikes than that awkward question.

    about uncut cocks – I love them! I mean, circumcised cocks are in effect genitally mutilated cocks, so I feel bad that American women are deprived of the wonders of intact cocks… how you suck them depends on the guy. try different things and see what gets him moaning 🙂

    • Yeah, I just really don’t like being put on the spot like that. I don’t have a clue what to say either. Other than “stop asking questions and just take me” because that’s what I REALLY want, lol. However, its decidedly not hot to have to TELL someone to “take me”…..

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  6. Recent reader, first time poster.
    As a man of Jamaican heritage who was raised by, with and around other immigrant Jamaicans in America, it’s a common fact that the best lovers in the Caribbean are a two way tie between Puerto Ricans and Trinidadians. Jamaicans (yes, I’m bragging) are known for size and power, not stamina or skill or (subjectively speaking) sensuality. I, myself, will ignore a dozen of my hottest countrywomen for a shot at a decidedly average Trini “gyal”.

    • And, lest I forget: for every woman who has no problem with a dominant guy who likes to “try things out”, there’s a woman who will see any sexual activity that deviates from their self-accepted norm as sexual assault or worse. Louis CK has a hilarious bit in his stand up about meeting a woman who wanted him to hold her down and force her to engage in sex in the first date. His response:”I’m not just going to rape a woman on the off chance that she’s into that type of sex!”

      • LOL, I admit I know men have it hard because women like things like “rape fantasies” but not real rape and it can be hard to know where to draw the line. This man actually told me that his wife was really anti sex and he would tell her he didn’t like feeling like he was raping her every time. So I’m pretty sure she is responsible for a lot of his hang ups too. That tends to happen. :p

    • Well hello and welcome! I haven’t heard the stereotypes about Caribbean men. This is the first time I’ve actually been with one other than a guy who was mixed with Hawaiian, Japanese, Jamaican and white and we didn’t actually have sex. Apparently now I need to go sample someone who is mixed with Puerto Rican and Trinidadian to compare 😉

  7. Pingback: The Referee and things the Prof never told me… | lifeofalovergirl

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