He sees the pained look on my face. I've tried anal sex twice before; on both instances the guy did it on impulse, without consulting me, and though I went along with it at the time, it was uncomfortable, and I felt violated and untrusting afterwards. Being a sex therapist, this is the kind of thing Ted helps me work through. His goal is to prepare me to have pleasurable, meaningful sexual relationships in the future. But, how we got from simple body awareness exercises, to this; I can't tell you.
"I know you've had some bad experiences in the past," he continues, "but, we've identified that your ass is a real source of physical pleasure for you. And, that it's the mental and emotional walls we need to break down. So, let's get started."
I take off my clothes as slowly as possible, procrastinating the inevitable. "As usual," he goes on, while removing his own clothing, "I won't do anything without asking you. And the moment anything isn't pleasurable, tell me. Don't tolerate anything. Ok?"
"Ok," I sigh, lying on the bed, as he's told me to do in previous sessions. I don't know if I'm ready for this. And as if reading my mind, he continues.
"I know you may not feel ready for this, but the point is to push your boundaries. How would you like me to start today?"
"I don't know," I confess, overwhelmed. He smiles, recognizing it.
"How about here?" He kisses my breasts, moving up to my neck, over to my shoulders, where he raises my arms submissively above my head, and kisses the underside of them.
"That's nice," I say, beginning to relax. He goes back to my breasts, where he tongues the nipples until they're hard. His hands graze my torso, and back up to my arms, where he encourages them to relax in the position above my head. This is to give him full access to my body. He lightly touches my breasts, brushes me all over with his hands; this is residual from earlier lessons in which he would do this, read my body language as to where I enjoyed being touched, and then asked if I would like him to linger there for awhile. More, less? Faster, slower? With my tongue, finger, or cock? If I seemed to be enjoying it but wouldn't answer verbally, he would tease the area until I was practically begging him for more.
"Ok," I sigh, lying on the bed, as he's told me to do in previous sessions. I don't know if I'm ready for this. And as if reading my mind, he continues.
"I know you may not feel ready for this, but the point is to push your boundaries. How would you like me to start today?"
"I don't know," I confess, overwhelmed. He smiles, recognizing it.
"How about here?" He kisses my breasts, moving up to my neck, over to my shoulders, where he raises my arms submissively above my head, and kisses the underside of them.
"That's nice," I say, beginning to relax. He goes back to my breasts, where he tongues the nipples until they're hard. His hands graze my torso, and back up to my arms, where he encourages them to relax in the position above my head. This is to give him full access to my body. He lightly touches my breasts, brushes me all over with his hands; this is residual from earlier lessons in which he would do this, read my body language as to where I enjoyed being touched, and then asked if I would like him to linger there for awhile. More, less? Faster, slower? With my tongue, finger, or cock? If I seemed to be enjoying it but wouldn't answer verbally, he would tease the area until I was practically begging him for more.
He kisses down my stomach, and I let my legs fall to the side, as he kisses my clit. His hands lightly brush over my thighs, the back of my knees, the cheeks of my ass. From doing this, he started touching my asshole, a few weeks ago. He would take the moisture from my pussy, and lightly brush the outside of it with his finger. He would also wander down to lick it, which I very much enjoyed, especially if he played with my clit while doing so, but I've been afraid to give the go ahead to go further.
When he sees me spread my legs and relax, I feel him rubbing the outside of my asshole again. I immediately tense up. "Now, just relax. I'm not going to go inside until you tell me to. Relax it for me, and I promise I won't go inside yet. Ok?" I relax my ass, letting his wet finger play with it's soft opening. "That's nice, see? That's much better." He licks my pussy, to help my relax further. He teases my asshole with his wet finger, this time letting the tip of it tease the opening until I'm bearing down, straining for more. "See? You're already opening it for me. You want it inside, don't you? Just a bit?"
"Yes," I admit.
"Play with your clit while I do it. I want to look at your beautiful asshole." This gives me the confidence to let him continue. "Let's see your pretty asshole open up for the tip of my finger. Can you do that for me?"
"Ohhh. Yes." I feel myself wide open for him, wanting it very badly.
"Let's see. Oh, it's so nice and open. I can move the tip in and out of it so easily." He does so, licking my asshole as he does it. He grabs the cheeks and spreads them, exposing it even more. "Oh, it's so pretty. I want to see my whole finger in it. Can you do that for me? You want it, don't you? I can tell." I nod. He spread my cheeks again, and I let my asshole relax, feeling it stretch a bit as he pulls them apart. "Oh, that's gorgeous. Look at that asshole," he says. "Get on your knees. I want you to really lean back towards me, and show it to me." I do as he asks. My pussy is fiercely wet, as I stoke it. I can feel it dripping on the bed beneath me. I love the way he is worshipping my ass. It makes it all feel so sexy. He plays with it for awhile, as before, in this new position.
"You like being on your knees don't you? You're opening up so nicely for me like this." He moves the tip of his finger in and out like before, while I hold in open, but he goes a little deeper each time. "You're doing so well. Hold it open for me while I do this, ok? Push towards me."
"Ohh, yes," as I do as he says. I almost reach out to his finger, pulling it inside. It slides in easily. It feels long and thin inside me, going quite deep. I'm not crazy about the feeling, and I retract a bit.
"Do you prefer that, or this?" This time, I don't know what it is, but it feels nice and full in my ass. It doesn't go very far in. "Thin, or thick?"
"Thick," I reply. He lubes me up, puts it back in. It's a short, thick plug, and he massages the outside of my asshole as he works it in.
"That's it. You're really opening up for me. Do you like to stretch it for me?"
"God, yes."
"Do you want to open up a little more? I think you can ..." He squeezes something else in there, perhaps a finger. I love the full feeling. I love that he's trying to cram more in there. I love that my ass feels like it's stretching. My pussy is dripping as I play with it, and I feel the urge to come.
"Yes! Just like that!"
"I'm going to put the tip of my cock in, ok? Just the tip. It's going to feel a little bigger than this. But I need you to stretch your ass for me, ok? Do you think you can do it?"
"Oh God, yes!" I feel his cock fumbling around my ass, as I strain towards him. The tip is rubbing against me, sliding around, just like when his finger was teasing the opening. It's driving me wild. I want it so badly. He then pushes the tip against it, like he's trying to get inside.
"Just open up for me. You want the tip of my cock to stretch your ass open? Do you?"
"Yes!" He pops it in, and when I trust that he isn't going any further, I really relax, open it up, bear down. The urge to come again. "Oh God, oh God!" I explode. He waits for me to finish, then takes out his cock, and lays beside me.
"Yes," I admit.
"Play with your clit while I do it. I want to look at your beautiful asshole." This gives me the confidence to let him continue. "Let's see your pretty asshole open up for the tip of my finger. Can you do that for me?"
"Ohhh. Yes." I feel myself wide open for him, wanting it very badly.
"Let's see. Oh, it's so nice and open. I can move the tip in and out of it so easily." He does so, licking my asshole as he does it. He grabs the cheeks and spreads them, exposing it even more. "Oh, it's so pretty. I want to see my whole finger in it. Can you do that for me? You want it, don't you? I can tell." I nod. He spread my cheeks again, and I let my asshole relax, feeling it stretch a bit as he pulls them apart. "Oh, that's gorgeous. Look at that asshole," he says. "Get on your knees. I want you to really lean back towards me, and show it to me." I do as he asks. My pussy is fiercely wet, as I stoke it. I can feel it dripping on the bed beneath me. I love the way he is worshipping my ass. It makes it all feel so sexy. He plays with it for awhile, as before, in this new position.
"You like being on your knees don't you? You're opening up so nicely for me like this." He moves the tip of his finger in and out like before, while I hold in open, but he goes a little deeper each time. "You're doing so well. Hold it open for me while I do this, ok? Push towards me."
"Ohh, yes," as I do as he says. I almost reach out to his finger, pulling it inside. It slides in easily. It feels long and thin inside me, going quite deep. I'm not crazy about the feeling, and I retract a bit.
"Do you prefer that, or this?" This time, I don't know what it is, but it feels nice and full in my ass. It doesn't go very far in. "Thin, or thick?"
"Thick," I reply. He lubes me up, puts it back in. It's a short, thick plug, and he massages the outside of my asshole as he works it in.
"That's it. You're really opening up for me. Do you like to stretch it for me?"
"God, yes."
"Do you want to open up a little more? I think you can ..." He squeezes something else in there, perhaps a finger. I love the full feeling. I love that he's trying to cram more in there. I love that my ass feels like it's stretching. My pussy is dripping as I play with it, and I feel the urge to come.
"Yes! Just like that!"
"I'm going to put the tip of my cock in, ok? Just the tip. It's going to feel a little bigger than this. But I need you to stretch your ass for me, ok? Do you think you can do it?"
"Oh God, yes!" I feel his cock fumbling around my ass, as I strain towards him. The tip is rubbing against me, sliding around, just like when his finger was teasing the opening. It's driving me wild. I want it so badly. He then pushes the tip against it, like he's trying to get inside.
"Just open up for me. You want the tip of my cock to stretch your ass open? Do you?"
"Yes!" He pops it in, and when I trust that he isn't going any further, I really relax, open it up, bear down. The urge to come again. "Oh God, oh God!" I explode. He waits for me to finish, then takes out his cock, and lays beside me.
"Oh wow..." I breathe.
"See? Nothing to be afraid of," he says with a smile. "Next time, we'll get the whole thing inside."
"See? Nothing to be afraid of," he says with a smile. "Next time, we'll get the whole thing inside."
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