A Strap-On Dildo Helps an Anal-Loving Lady Try Something New

I’ve always wanted to be double penetrated, but I’ve never really been interested in having a threesome. I know it makes no sense, wanting one but not the other, and I didn’t really think I’d ever get what I wanted that way. It was a fantasy I figured I’d have to give up sooner or later. At least that’s what I thought before Thomas went shopping.

He’d called me before our date on Saturday and told me that he had a surprise for me. Thomas made me wait through a movie, dinner, and dessert before he’d let me see my surprise. Back at his house, he handed me a bag and watched expectantly as I opened it. I pulled out a tangle of straps and looked at Thomas questioningly. He gestured for me to keep going, and I continued to dig through the tissue paper. At the bottom of the bag was a slim black dildo with a large round base. That’s when I realized what he’d given me: a strap-on.

I had no idea why Thomas would buy me a strap-on. It didn’t seem like something either of us would need. He’s not interested in being pegged, so I couldn’t use it on him, and I had no idea why he would need it when he already had a dick of his own. Thomas simply smiled and told me to wait a minute, and then I’d understand everything. So I sat on the bed and waited for him to make things clear.

As I watched, Thomas stripped out of his shirt and slacks and boxers until he was naked. Then he stepped into the harness and pulled the straps up his legs and around his hips. He faced away from me as he tightened the harness, but I could see him pulling on the nylon straps as he cinched the strap-on around himself and settled the dildo into place. When he finally turned around, what I saw surprised me.

His cock was hanging down through a ring in the front of the harness, and the dildo jutted out an inch or two farther up his pelvis. It made it look like he had two dicks—and suddenly I knew why he’d bought the harness. With the harness on, he could fuck my pussy and ass at the same time, no second man necessary. I couldn’t believe I hadn’t thought of that first!

Thomas looked at me and asked if I wanted to “give it a whirl.” I didn’t have to say yes. The way I jumped off the bed and kissed him was a dead giveaway about what I wanted. My boyfriend’s cock rubbed against my thigh, while the dildo rubbed against my stomach, and feeling both of them at once was a huge turn-on for me. I couldn’t wait to feel them inside my holes.

As we kissed, Thomas started pulling off my clothes, first my shirt and then my skirt. I helped him along, unhooking my bra and sliding my panties down my hips. Once my clothes were off, he moved in closer and started rubbing his hands up and down my body. My pussy was already wet with anticipation, and when his hands slid down to cup my mound, I jumped. His finger slid inside me, but I wanted to feel something else.

I started grinding against Thomas, and his now-hard dick pressed against me. I moaned as I felt it graze my center, and I begged him to fuck me. But he wasn’t going to give it up so easily. He fingered me for a moment before reaching around and lightly stroking my ass. I moaned even louder as one of his digits pressed against my rear hole, and when it entered me, I cried out in pleasure.

I love when Thomas fingers my ass, and having him do it then, when there was the added promise of being fucked in the ass, was even better. He kept his finger in my back hole, working it deeper and deeper, and when he couldn’t thrust his finger in any farther, he pulled it out and pushed me down on the bed. We were both panting when he climbed on top of me, but it was clear neither of us could wait to catch our breath before we started to fuck.

The slim black dildo slid slowly into my cunt while he nudged his dick into my ass. Having both holes filled at once was a unique sensation, and I couldn’t believe how good it felt. I shifted slightly under Thomas to work both dicks farther inside, and as they started to fill me, I wondered why we’d waited so long to try something like that.

When both holes were stuffed, Thomas stopped and let me get used to the feeling of having a dick in my ass and my cunt at the same time. I’d wanted to experience the sensations for so long that it didn’t take more than a few seconds for me to get accustomed to it. Then Thomas started to fuck me.

The dildo moved in and out of my slit at the same pace that his cock moved in my ass, and I felt my climax building up twice as fast as usual. His dick was thicker than the toy, but both slid in and out of me with the same ease, allowing Thomas to pick up his pace and thrust harder. The faster he pumped into me, the better it felt, and in less than a minute I was writhing beneath him, trying to meet each of his strokes.

He worked out a rhythm, one that sent shivers of pleasure down my spine, and each thrust brought me closer to my climax. As he fucked me to orgasm, I felt his dick and the dildo rubbing together through the thin wall that separated my pussy and ass, and that simple sensation drove me crazy. There was nothing I could do but lay back and enjoy it.

Thomas sensed that I was on the edge of my climax, and he started switching things up, thrusting at a constantly changing pace, never letting me figure out what he was going to do next. Each time I tried to match his thrusts, I failed, but it only made the sensations feel that much better. As his thrusts became more unpredictable, I felt myself start to slip over the edge. It didn’t take more than a couple of minutes of his erratic movements to push me over completely, and when it did, I practically screamed with ecstasy.

Thomas didn’t stop there. He kept going, continuing to fuck me through my orgasm and quickly working me up to a second. While the first one had been in my pussy, the second orgasm felt like it originated right in my ass, and I felt my sphincter clench hard around my boyfriend’s cock as I came. As my ass gripped his cock, Thomas came, too, and I felt him shoot his load deep inside me.

When he finally pulled out—of both holes—I saw that his cock had started to go limp, but the dildo was still rock hard. Even though I’d already come twice, seeing the dildo still stiff and ready to go, well, I was ready for another roll in the hay. Thomas’s surprise was turning out to be even better than I’d originally thought it would be! I couldn’t wait to see how far we could go with the help of our new toy.

—Ms. Lana F., Via Email