Short Sex Stories

Pleasuring Him (Male Virgin)

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Theo and I have been in a relationship for more than two months now, but we haven't yet been sexual. You see although, this isn't my first relationship, I am Theo's first-ever girlfriend.

When you spend most of your teenage and early 20s unseen and with low self-confidence, and then you hit the gym at the age of 24 and become a tall handsome jacked guy. Instead of a tall skinny nerdy boy, things change.

That's where I and Theo met, in the gym. He was my gym crush and one day when I actually spoke to him breaking the ice, turns out I was his gym crush too. But although he looks much different now, he is still a bit shy and underconfident when it comes to sex.

He is a virgin and I have slept with two guys before so I have some experience in these matters.

It's his birthday today and I have planned to give him a special gift, apart from the wristwatch I have got for him and the dinner.

"Happy birthday, birthday boy," I called him in the morning.

"Thanks!" he replied in his shy tone. Looking at the guy you would never know that this guy is so shy and introverted and that's what I loved about him.

"So, you meeting me at the Grant Central Hotel right."

"You know you don't need to do all this right, I'm just happy having ramen and watching Netflix with you at my place."

"Well, we can do that any day, but my boyfriend does not turn 25 every day. So, I had to do all this."

He chucks in that deep voice of his and says, "Fine I will see you there, got to get back to work."

"See you and love you."

I was in Victoria's Secret Picking the perfect pair of lingerie for the occasion. I wanted to blow Theo's mind and give him the most perfect first time.

That evening when I reached the hotel a little while before him, as I had also booked a suit in the hotel for us. I made sure that the room was perfect and cost enough to make him comfortable.

Exactly around seven Theo got there, he was still in his work clothes and I was dressed in a slim long satin gown. I was settled on the table reserved for us and the moment he saw me the delight in his eyes, was enough to tell me he loved what he saw.

I got up and kissed him.

"Happy birthday once again my love," I said to him.

"Thanks, babe." He replied kissing me back.

The dinner went smoothly and he loved the wristwatch I had gifted him.

"Let's go, I will drop you off and then go home," Theo suggested.

"Well actually... um...I had planned something more for you." God knows why I was feeling shy too, Theo was an imposing man to look at even though I knew how gentle and loving he was with me.

He lifted my chin with his fingers and asked me, "What is it?"

"I booked a room for us upstairs to spend a night together."

Theo looked surprised as I had never initiated sex before, knowing he was a virgin, I always took it as per his pace.

"So, what are we waiting for." I had not expected him to be so eager. I smiled held his hand and led him towards the elevator. I had the room keys in my purse and as soon as we got into the elevator. Theo pressed me against one wall and began kissing me.