My Boyfriend Stretches My Pussy

My boyfriend and I have a special routine. I've always been pretty tight and he's well, pretty well-endowed. Sex was always uncomfortable until he started stretching my pussy. It might sound strange to others but it's what works for us. It's hot and intimate and I love it, even when it's a little hard to take.

Every Wednesday night, I take a hot shower. The heat helps my body relax. He waits for me in the bedroom, where I remove my bathrobe. He lays me on the bed and spreads my knees. Then he brings me to orgasm with his fingers and mouth. He likes to make me cum during our stretching sessions. He says it loosens me up and helps me take it better.

After my first orgasm, I position myself across his lap. My pussy is always nice and wet by now, but he still lubes me up with a generous dollop of KY jelly, sliding his fingers in and out of my slippery hole. That's how he looks out for me. He inserts the smallest dilator that we use, and with his other hand he begins to knead and pinch my breasts and nipples.

My boyfriend knows I love having my breasts handled roughly. It feels especially good across his lap as he works the dilator in and out. The position feels cozy and vulnerable at the same time, like I'm his personal toy. Before long, he moves onto the next size up, which fills and stretches me just right. He likes to hear me moan, and the second dilator always makes me moan a ton. He stays on this size for quite a while, gradually moving it harder and faster. Sometimes the sensation coupled with his handling of my breasts is enough to make me cum, which pleases him greatly. My boyfriend likes it when I orgasm from the dilator, without the need for clit stimulation. It tells him that my body is getting the treatment it needs.

Then he moves onto the largest dilator, which is a more challenging size for me, though it doesn't compare to what comes next. He pushes it in more slowly than the previous two, knowing I need more time to adjust. I take deep breaths and concentrate on relaxing my muscles to accommodate its girth. Despite the discomfort, I never fail to get extra wet as he steadily works it in and out of my stretched pussy. What can I say, my body likes it when someone else is in control.

When he finally slides it out of me, I know what's coming next. Sometimes I feel primed and ready for the challenge. Other times, if I struggled with the last dilator, I can get a little apprehensive. I wouldn't dream of asking him to stop, though. My boyfriend knows what's good for me, and he's just giving me what I need.

He lubricates the inflatable dildo and eases it into me, slower than he needs to. He knows I need time to mentally prepare. Gradually, he inflates the dildo until I hit my limit and start to whimper. He helps me relax by stroking my hair and reminding me to breathe. Once I manage to relax, he inflates the dildo further. We repeat this process, with him slowly inflating the dildo as I relax my pussy muscles little by little, until it reaches maximum inflation.

This part is always hard to take. I have to work hard to relax my muscles or it feels like I am being torn apart. I am good at this now so it only hurts a little, but the dildo stretches me so wide and fills me so completely, it scares me and makes me feel utterly vulnerable and helpless. I don't know why I feel this way, but I love it. I should hate it but I love it. I can't explain it but it just feels so right.

Once my boyfriend gets the dildo to maximum inflation, he deflates it to give me a break. While we wait, he will start fondling my breasts again, and twisting and tugging at my nipples. By now I am usually moaning uncontrollably. Before long, he begins to reinflate the dildo, without stopping this time, until it is fully inflated, and holds it for a count of 30. I squeeze my eyes shut and whimper until he releases the pressure, only to start inflating it again.

Eventually he decides I've had enough and this part of the session comes to an end. He fully inflates the dildo and holds it in place with his thumb, while with his index and middle fingers he begins to stroke and massage my swollen clit. His other hand continues to work my breasts and nipples. Despite my suffering, it never takes me long to cum like this. To be honest, I think it makes me cum harder. I've always responded that way to feelings of helplessness. It's just the way I am.

My pussy always feels empty after he removes the dildo from it, and I almost miss the impossibly full sensation that came before. Sometimes my boyfriend likes to fuck me in this state - his cock slides in easiest right after my stretching, and I'm always in a very receptive and submissive state. Other time he prefers to just hold me while I come back to my senses. Sometimes I drift off to sleep like this and it's the most wonderful way to fall asleep, thoroughly stretched, aching and exhausted. I truly do love our special routine.