Lay back for missionary

You lay back, spreading your legs as if to invite him to crawl between them. He does so, pulling off his shirt in the process. He reaches down and grabs his condom-encased shaft and lines himself up to enter your slit. You feel him press the head at your entrance, but it doesn't seem to want to go in. As he pushes harder, it only causes you more discomfort. "Are you sure that's the right spot?" you ask him through gritted teeth.

"Yeah, I'm sure; just give me a second." This time he pushes quickly and firmly, and you feel a popping sensation as he finally enters you a few inches. A stinging pain erupts in your crotch as you are filled. He pulls back and pushes in again, trying to get deeper. The first couple of inches that were already inside of you slide out and back in smoothly, but once again, there's trouble once he reaches the portion that had not yet been inside. Alex pulls out completely and spits into his hand, ready to rub it on his shaft to help lubricate the way. He looks down and pauses for a moment. "The cond--" he starts, then pauses. "Nevermind." He rubs the spit in his hand onto his shaft and lines himself up again.

"What is it?" you ask him, wondering what it was he wanted to say.

"Nothing," is his terse response as he enters you again, this time driving deep in one smooth stroke until his entire cock is embedded in you. You mewl your pleasure, forgetting suddenly about the pain you felt as he entered you the first time.

He starts thrusting into you in long, slow strokes. You can feel the heat from his cock against the inside walls of your vagina. His dick feels silky smooth as he pushes and pulls, the sensation arousing you even further. In your wildest dreams, you had never imagined sex feeling this good. You wrap your legs around his waist, pulling him into you harder with each thrust. You look up at Alex as he thrusts into you, and you see his face starting to contort. You can tell he's close, and you're somewhat saddened that you're not likely going to get your own release if he finishes so quickly. Even so, now that you know what sex feels like, you're going to have to pick up a big pack of condoms so you everything that moves until you turn back into a guy.

"I'm getting close," Alex says, and you mewl your approval. "I'm gonna cum!" he announces.