His First Valentine

Jack mostly spends his Valentine’s days alone. Now that he was twenty two years old and living on his own, he had no one to talk to. There were only a few women in his apartment; one has a husband, another has a boyfriend who also away on business and an elderly woman who is tired of hearing all of the fucking from behind the walls every night.

“Turn that shit down. I’m trying to sleep.” She shouted while banging her fist on the wall. However Jack was unfazed by it. It was about to be Valentine’s day and he always dreads it. Throughout his life, he had never received a gift from anyone or even had a girlfriend. He instead reads the catalogs with the models posing in their bra and panties and mostly jerks off to them. His penis was usually hard for the woman whose boyfriend goes away on business trips. Her name is Vanessa and she lives down the hall from his apartment.

When Jack saw Vanessa with her boyfriend, his first thought was “what the hell does she see in him? Not a goddamn thing.” Every time her boyfriend would go on an out of state trip, she would be alone too. She mostly stayed at home watching television and thought about what she could be doing with him. However since he was always on the move, it was never possible. With Valentine’s day around the corner, she had hoped to spend the day with him. She even secretly bought new lingerie to wear that day, which he had not seen. But of course, he had packed to go on another trip. While he was packing his clothes, Vanessa saw a text message from another woman saying what time he will meet her at a hotel. She was upset at what she saw but quickly acted like nothing had happened.

After he left, she had cried realizing that these trips were false so he could have an affair. Meanwhile, Jack bought himself a box of chocolate which he always does. Before he could eat the first piece of chocolate, he heard a knock on his door. It turns out to be Vanessa in the doorway, wearing a dark brown trench coat and holding a bouquet of flowers. As she entered the apartment, Jack was so confused about what was happening. She then explained what she saw on her boyfriend’s phone. She realized that he had been secretly going on dating apps and masturbating to the pictures he would receive through messenger. Now that he went on his “trip”, Vanessa wanted to have her fun too.

She noticed Jack was all alone and eating chocolate by himself. She then places the bouquet on his kitchen table, unties her trench coat, and reveals to be in a half buttoned white dress shirt and a purple skirt. Jack was stunned to see what was right in front of him. But she in turn was shocked to learn that he had never had a Valentine before, even had to show her proof. He was just a poor single guy with no luck. Vanessa then quickly goes to the bathroom to change.

After she exits the bathroom, Jack sees her in a small pink robe and matching pink bra and panties, which she originally bought for her boyfriend, but he will never get to see it. Jack started to feel an erection through his trousers, which Vanessa unzipped and saw his full erection. The two went to his room and they kissed while getting undressed. Vanessa unhooked her bra, revealing her big tits and she removed her panties too, throwing them on the floor. She was riding on top of Jack, as his dick was throbbing and cumming inside her hairy, also throbbing pussy. Then her big shapely ass and curves were bouncing up and down on his erection, with her thighs shaking. By the time it was midnight, Valentine’s day was over. They both lay next to each other, smiling.

“Happy Valentine's day.” she said to him, kissing him on the cheek and hugging him.