loving anal.

I want to try anal sex with my boyfriend.

I know, I know.  I know what it looks like.  But it’s not a split second decision this time, I swear!  Perhaps for the first time in my life, I’m in a loving relationship; have been for almost a year now, and well, we’ve been experimenting a bit.  Nothing too crazy or kinky; it’s more that, I just feel like we are finally becoming comfortable enough in the bedroom to slow down and really start listening to each other.  And in the process, he’s been giving me some attention down there.  I have to say, I find it very pleasurable.  At times.  It’s tricky.  Let me explain.  

It started with my boyfriend, Thomas, going down on me.  It would drive me crazy to have him lick my clitoris, and feel the bottom of my pussy with his fingertips.  Just laying two fingers at the bottom of my opening, solely under the pressure of their own weight, was enough to drive me wild.  Soon, I found myself enjoying when Thomas would rub the area between my pussy and my ass very lightly.  Apparently, there is a whole circuit of nerves down there that I wasn’t aware of!  I googled it.  Some women are more sensitive on their perineum, then any other part of their body.  But that wasn’t the only thing I enjoyed about it.  Every so often, while massaging this area, Thomas would, ever so slightly, graze my asshole.  It surprised me very much that I didn’t mind.  And not only that, I soon found myself craving him touching me there.  So much so, that this became the new game for me: while Thomas lovingly licked me and tickled my pussy, I was getting off thinking of how badly I wanted him to touch my ass, and came sometimes solely from him mistakenly brushing it with the side of his hand.  I even masturbating thinking about it, and alone in my bed with my vibrator on my clit, I could feel myself bearing down, and almost reaching out with my ass right before I came. 
 Wow, I thought.  I need to tell him about this.

  “Baby, you’re driving me crazy!”  I exclaim, the next time he’s licking me.  I rotate my pelvis further forward, almost curling myself into a ball, trying to expose myself to him.  “Uuggghh!”  Perhaps out of pure exhaustion, I let my stomach muscles relax a moment, laying flat, then thrust forward again, leaving his hand a step behind.  Lingering on my ass.  “Yeah, baby,” I breathe, already feeling like I could come.  “Touch me there.”  He gives me exactly what I’ve been craving: his lovely light gesturing fingertips, and I don’t exactly stick around long enough to enjoy it.  I come hard and fast, with the fury of all my recent fantasies, and it’s so aggressive, that Thomas can’t help but laughing. 

        “Wow, baby,” he smiles.  “That was a crazy one.  You like that?”  Still out of breath, I smile, groping for him beside me.
       “Oh yeah.  That was perfect.  I’ve been dreaming about that.  Literally.”  He raises his eyebrow, with an inquisitively look in his eye.
       “Oh really? What have you been dreaming about?”  I laugh, in my post orgasmic glow.
       "I don’t know exactly.  But, it seems to be the only thing I can think about lately.”  
       “Okay,” he says, nodding, processing the information.  “I’ll try some things.”  

Soon, being touched on my asshole, moves on to putting a finger inside.  When he does it, it doesn’t initially feel pleasurable, but it always make me come in the end, regardless.  Touching the outside easily sends waves of pleasure throughout my body, but when he’s inside, it’s almost as if you have to get past the uncomfortable part, to get to the orgasm.  It’s only when I fully relax and open that part, deep inside, that it happens.  It often feels foreign, and forced, right up until the moment I come, like a doctor’s exam, only with a happy ending.  I’ve even purchased a small butt plug for myself, when I masturbate.  I dislike putting it in and taking it out, but the middle part is enough to keep me coming back again, and again.  The thought of Thomas burrowing inside, trying to reach that special spot, remains wildly erotic for me, and there’s an added mental element of it being taboo, as well.  I wonder if the orgasm comes from what I happen to be thinking at the moment, rather than what’s being done to me. If I’m actually opening up and letting him inside as I say, or it is just the thought of doing it that makes me come.  In any case, my clitoris is still being stimulated, which makes the experience highly sexual, despite any reservations.  We try some role play.

“I know this is going to feel a little weird, but I really need to massage you here, Okay?”  Naughty Masseuse, we’re finding, really helps to bridge the gap.
         “Okay,” I hesitantly respond, in character of course, using my vibe on my clit this time.  
         “People have so much tension here, you have no idea.”  He touches me on my ass, lightly massaging the outside of it with a bit of lube of his fingers.  The sensation leaves every part of me straining to be touched.  I think they call it, “good tension”.  Placing a small amount of pressure, he uses the pads of two fingers in a circular motion over me.  “I know this isn’t usually done, but it’s very important, okay?”  I moan; concentrating, buckling down, getting in the zone.
         “Mmmm. Okay.” 
         “You just have to relax it for me, Okay?  Only when it’s nice and soft, can I continue.”  I take a deep, relaxing breath, resting my face next to his, beside me.  I like it when he talks about what he’s doing to me, and have told him so.  I feel my ass open up, almost reaching towards his hand.  When he notices a change in my body, he says, “Good.  That’s perfect.  You’re doing very well.”  This kind of talk turns me on so much, it wouldn’t matter what he was doing to me.  “Now, I’m going to massage inside.  I know it won’t feel very good, but I need you to do it.”  
        “Ohhhhh, yeah,” I sigh, turning the vibrator up slightly. 
        “I’m going to go very slowly, because it’s important that you keep relaxing it, okay?”  He says, squeezing more lube onto his finger.  He begins to tunnel his way in, in a circular motion, seemingly massaging the walls as he does so. 
         “Oohhhh,” I breathe, as I bear down on his finger.  
         “I just need to you relax and let me in, okay?  I need you to open right up for me, so I can get inside.”  Oh my god, he is so good at this.  “I’m going to put more in, okay?  I can’t quite get there with one finger.  You’re too tight.  I need to make this nice and loose.” 
         “Fuuuuuuuuck,” I moan, trying to do as he asks.  It feels as if he’s almost there.  He’s almost touching that spot.  I just need to.  Oh.  I just need to.  Just then, as I’m trying to navigate it, he forces another finger in, and I can’t believe how full it feels. The thought of my asshole stretching open brings me over the edge, and I have such an intense orgasm, that apparently, I scream out.  I have no recollection.  

"Baby!!”  Thomas exclaims, afterwards, laughing.  “You’re amazing.” 
          “Was that okay?”  I ask, conscious of how much time and work it’s becoming to make me reach orgasm.
          “It was amazing,” he responds, lifting my face, and planting a kiss on my lips.  “Did you have a good orgasm, baby?”    

The fantasy of anal play continues to monopolize my thoughts, and my mind soon moves to having Thomas’ cock in there.  But, as much pleasure as I’m getting from anal play now, it still makes me nervous.  This time, however, I’m sure it will be different.  I’ve had anal sex before with a couple old boyfriends, and we never had the kind of foreplay, communication, or quite frankly, love, that Thomas and I engage in now.  Just kind of a split decision that they did in the heat of the moment, resulting in it not being terribly pleasurable for me.  But, I think Thomas and I can do it with much better results.  I’ve been reading on it.  Lots of straight women enjoy anal sex with their partners nowadays, and some can even come from it, if done properly.  And I think I could, too.  What Thomas and I have been doing in the bedroom certainly suggests it.  And once I get my mind on something, I don’t know why, but I just have to do it.    

“We have to go really slow.  Maybe we can start with the tip, and I can let you know when you can give me more?” 
         “Sure, baby.  Whatever you want,” Thomas responds warmly.  We’ve had the usual foreplay, with me using my vibrator on my pussy, and him playing with my ass.  He actually put three fingers in this time, and it was feeling really relaxed and open.  I think I’m really learning how to do it.  And I think that when it comes to anal sex, the fact that I’ll have my vibrator on my clit this time, will make a huge difference. 
         “Can you just rub your cock against me for a while?”
        “Yeah, baby,” he says smiling, getting behind me in a spoon position.  
        “Can you kiss me?” I ask, wanted to keep relaxed and in a state of arousal.  I turn my head to meet his mouth, and he gives me a few warm, wet kisses.  I rest my head back down, as he continues to kiss the back of my neck, and shoulders.  “That’s nice, baby,” I sigh into the pillow.  I turn the vibrator up a setting, as I feel his cock rubbing against my ass.  “Mmmmm.  Just do that for a little while, baby.”  He reaches around and touches my breast, nuzzling his face into my back.  I feel the head of his cock fumbling around between my cheeks, I reach back, touching the length of his torso, pulling him against me.
          “I want to feel your body against me,” I breathe, as he spoons me completely, and I feel the warmth of him on my back, butt, and thighs.  I rotate my hips back into him, and he presses back.  I can feel his hard cock sandwiched between us, and I reach down to grab his hip as we press ourselves into each other.  I want to feel as much of him as possible against me right now, and I savour the hug.  With the vibe on my pussy, it feels sensual, and safe.
         “Why don’t you put some lube on your cock, baby?  And rub it around my ass?”  
         “Mmmm,” he moans, kissing my ear.  “I love you.”  I feel his absence from the back of me, as he parts to grab the bottle.  

I continue to breathe deeply, reminding him to use more than he thinks we’ll need.  “Too much is just enough, they say,” I quip, and he laughs.  
            "I can always add more as we go,” he says, kissing my shoulder.  “Let’s just see how this goes first.”  I take another breath, concentrating on the sensations from the vibrator, and I suddenly feel his lubed cock slide over my ass.  I rub myself with the vibe, and try to relax my asshole, making it soft.  When I do, the tip of his dick dips in ever so slightly.
            “Ohhh,” I moan.  “That’s nice, baby.  Keep doing that for a bit.  I like the way that feels.”  He lets it slip in couple more times, and dirty talks in my ear.
             "I want you to keep it open while I do this, okay?  Keep it nice and open so that my cock slides right in, without even trying.”  I turn my head to kiss him; giving my tongue, and taking his.  Every part of me feels warm and wet.  I want him so badly. 
             “Can you give me the tip, and hold it there, baby?”  He repositions himself on his elbow, and I feel it enter, just like before, then it sort of pops in, and it’s too much.  Then it slips out.  “A little less, baby.”  
             “Okay, I’ll try.”  I massage myself harder with the vibe, moving it down to the opening of my pussy, and back up again, drawing moisture upwards.  

I feel the tip of his dick position over me, go in slightly to where it feels good, then falls out again.  “It’s okay, baby,” I soothe, “It feels good when you do that.  That much feels good.”  He rubs his cock over my asshole again, approaching it from another angle, but it slides right back out.  “Ooohh, that’s nice baby.”  I feel like it might be a little frustrating for him to do this, but I want him to know that this is part of the foreplay for me, and that having his cock playing around my ass like that feels great. 
             “I don’t think I’m going to be able to hold it in,” he says. “It’s got to be really hard.”  I feel slighted for a moment, that the thought of fucking me in the ass isn’t enough for him, but he finishes, “I’m just nervous that I’m going to hurt you.” 
             “Oh, baby.  Don’t worry,” I turn to him, kissing him on the mouth soothingly, but determined.  “Just give me as little as you can, then.  And hold it there, okay?”
            “Okay,” he says, leaning back to put a little more lube on his cock.  He leans back into me, and I feel it pop in, then push slightly, stretching me uncomfortably. 
            “Okay, okay!” I say, perhaps a little too alarmingly.  Adding, “It’s ok, just don’t move.”  I furiously rub the vibe on myself, as I try to relax around his cock.  A couple minutes go by, and I try to get in the mind frame of when he plays with my ass with his fingers.  I try to bear down on it, almost pushing towards it.
            “I don’t know how long I can do this for,” Thomas says, slipping out already, then compensating by pushing in a little more. 
            “Oh,” the syllable jumps from my mouth.  “Move in and out a bit, then,” I say encouragingly, not yet wanting to give up.  “See how that feels.”  He minutely thrusts, very slowly, and I keep my ass as open as I can.  He moves in and out of me, and it feels like it could get to pleasurable.  Maybe.  Oh.  Maybe, maybe.  If I can just.  Oh.  Just.  He speeds up a bit, and I feel my muscles stop engaging.  I stop pushing and bearing down, but it doesn’t matter, he continues to thrust easily, because there’s so much lube.  I put my hand on his hip to stop him.  “Okay.  Pull out, baby.  Slowly.”     

“Are you okay?”  Thomas asks, lovingly.  “I didn’t hurt you, did I?” 
          “No, no, baby,”  I’m quick to add.  “I’m fine.”  But I feel myself collapsed flat on the bed, unwilling to move.  My body feels quite expended.  He reaches to rub my back.
          “What’s wrong, baby?  Are you okay?”  
          “I’m fine, baby.  Don’t worry,” I respond, but unable to get up and shake it off quite yet.  He sees my tired face.
           "Oh, baby.  I’m sorry.  I thought ...”  I reach up, eyes closed, and put my hand in his hair. 
          “I know.  It’s my fault.  Don’t worry.  Come here.”  He brings his face towards mine, burying it into the pillow, near my ear.  
          “You’re not hurt, are you?  Oh baby...”  
         “Shhhh, no.  I’m just tired.  It was just, a lot.”  I feel cold, suddenly, like I’m coming down with something. 
         “Oh baby, why did we do that?  I feel so bad,” he says, holding me, rubbing my cool skin with his warm hand.  Why did I do that?  I’m so stupid; I feel like I just gave birth!  He makes a move for the covers.  
          “We should clean up,” I say before he can. “Let’s take a hot shower together.”             

In the warmth of the shower, I shiver a bit, and Thomas stands and holds me under the stream of water until I stop.  “I don’t want to do that again anytime soon,” he says, slowly rocking the hug side to side. 
            “Oh, baby,”  I say, feeling more like myself.  “I’m fine.  But, no,” I laugh, “We don’t need to do that.”  
            “I hope you don’t feel that I pressured you in any way,” he says. 
            “No,” I respond, lifting my head from his chest.  “Of course not.  If anything, I pressured myself into it.”  He pulls me close again, with his chin resting on my head.
           “Oh, baby,” he says, “I just want you to be happy.  I don’t need anything.  I don’t want anything else.  You give me everything I need.”  We hug tightly, under the warm shower head.  
           “I love you,” I say, looking up into his eyes.  He leans down for a closed mouth kiss, but I feel myself wanting his warm tongue.  Our lips part, and I swirl mine into his mouth, pulling his face into me with my hands.  His erection is back almost instantly, and I relish finally grabbing it in my hand.  He puts his arms around me, and I’m so relieved and happy to be face to face with him again.  I continue to kiss him deeply, grabbing the soap to liberally lather his cock.  He leans forward with his hips, head tilting back in pleasure.  He massages my slippery, soapy breasts for a moment, but realizes I want to do something for him, now.  I love the feeling of his hard cock in my hand, and I jerk it until he shoots half way across the shower.  

        Just like usual.