Trials of Adulthood

Tony laughed off the nerves as he took off his blouse, revealing a black bra supporting two large breasts. He was no longer a 21-year-old man, but rather a woman approaching middle age. As such, he felt it was high time he lost his virginity. After doing some searching online, he found a geeky and naive man named Simon who was also a virgin. Tony figured it would be safest to be with someone in a similar situation.

While sitting on the hotel bed together, Tony grabbed Simon's hand and brought it to his right boob. "There, now you've touched a woman's breast," Tony said. Simon, however, was too stunned to pursue further action and put his hand down. "No, please keep touching me there. I like it," he continued, bringing Simon's hand back up. "Believe me, it feels good. Just don't squeeze too hard. I'm still getting used to them." Foreplay was ending up almost frustrating with someone so inexperienced.

"I'm sorry," Simon responded. "I'm just a little nervous. I don't want to do something wrong.

Tony said nothing at first. He just looked into Simon's eyes before deciding to take a bold move. He reached straight for Simon's penis and began fondling it through the pants. Simon sharply inhaled and Tony felt it immediately began to grow at his touch. Then he spoke. "I brought you here to have sex with me. I'll tell you if you're doing something wrong. Now kiss me."

The moment of leaning in for the kiss stretched into an eternity. Every breath, every micro-expression, even the slightest tilt of the head. As Tony and Simon got closer and closer they began feeling each other's body heat. Finally their lips touched, and they both followed through with what they expected a kiss to be. It was slightly awkward, but as hot as raw passion could be. That seemed to give Simon all the permission he was waiting for.

Before Tony knew it, he was in Simon's lap getting his pussy pounded. Simon's dick pumped in and out of him with such rapid ferocity, creating a sensation of fullness and pleasure he could have never imagined before. Any expectations of behavior or the need for formalities quickly went away as they both succumbed to animal instincts. Tony needed to be fucked. He needed to feel a penis thrusting deep inside him. He unconsciously wrapped his arms around his partner for support and intimacy as the pressure in his groin built up towards orgasm.