How I lost my virginity to my high school sweetheart

This has been going on for months now me waking up from a sex dream, panting with my heart throbbing like crazy. In my dreams, I am always making out with someone hot but his face is hazy and lost my virginity as well. I talked to my girlfriends about this stupid dream. My three best friends since high school- Samantha, Natasha, and Lisa, have been my constant companion and I share everything with them. Samantha was playing with her hair and her hand froze. She looked at me and said, “Finally, I was waiting to hear you say that, Jennifer. It’s being two months since you broke up with Robert. Just call him and just get laid.”

“Exactly,” said Natasha. “So, was it with Robert? I told you to have sex with him during your relationship. But no- you wanted to wait a little longer.”

“He doesn’t have a face.” I replied.

“So, you were just having sex with a faceless guy in your dream. “Mused Samantha.

I walked back home that evening feeling confused and slightly desperate. Was I being too coy and ended up losing the best guy? And now I am raging on hormones and having twisted fantasies in my dreams? I decided to call Robert.

“Hello Robert this is Jennifer.”

He exhaled and took a pause and said, “I know who you are I have your number saved. What is it?”

“Let’s meet. 6PM at my place. There are some things to discuss.”

I was seething with excitement and carefully chose my outfit and style. I was going to have sex. Virginity is not worth losing the guy I love. I was wearing a lacy see-through red gown, straightened my hair, and waxed my leg to perfection.

A couple of minutes before 6, the doorbell rang. His jaws dropped as he saw me. I knew I looked hot- I was confident. I always had an athletic body with shapely and perky boobs. Today, they were even more highlighted by the low-cut neckline of the dress. Red has always looked the most flattering on my alabaster skin.

He sat comfortably on the couch and looked straight on my face.

“So, you wanted to talk to me?”

I took a deep breath and was about to start talking when he jumped up from his seat and came on me and kissed me hard.

“You really just want to talk, wearing this dress? Do you want to seduce me?”

My throat dried up and I replied, “Maybe and then I thought for a while about the dream of how I lost my virginity”

He started kissing my throat slowly and softly. He left a trail of kisses from my ears, forehead, nose, and finally my lips. I was a bit shocked trying to fathom what we were about to do. But as he kept kissing me, I forgot all my reasons for putting this off. This was the best feeling in the world- his arms. How could I not see that so long?

He suddenly looked up and asked hesitantly, “Do you… Want to go all the way this time?”

I looked straight in his eyes and replied confidently. “Yes. I want to have sex”

It seemed like my consent was the ultimate turn-on for him, just as I imagined how I lost my virginity. He stretched my dress and popped out my boobs. As he nestled them in his hands and sucked, I played with his hair and twisted my legs around him. Suggestively, I drew my legs together to lock him in between and smiled. He got the signal. He was up in one fluid movement and carried me in his arms to the bedroom.

He plopped me on bed and dived in beside me. I giggled and tried to hold him but he was too fast. He grabbed both my wrists in one hand and pinned them above my head. With the other, he was already caressing my hip bone and slowly pulling down my panty.

I was already dripping wet. This is the furthest any guy has ever explored my body. I trembled in anticipation as he was taking off his clothes. When his boner sprang out it finally set in my mind that we are going to have sex! I am losing my virginity finally! I panicked a bit and blurted, “Wear the condom!”

He laughed, “Of course I will.”

He took out a condom and rolled it down his length and then positioned between my legs. He lightly nudged my vagina with the tip of his dick and sent a jolt through my body. Then he poked harder and pushed the tip in. I felt a stab of pain and panted but did not say anything for I didn’t want him to stop. He pushed harder still till he was completely in.

“Gosh Jennifer! You are tight!” he exclaimed as he pushed even harder and this time I cried out. He was taken aback and bit and quickly withdrew. He looked down on his dick and when he saw the blood, he comprehended what just happened.

“You were a virgin? Is that why you never wanted me to have sex?” I whimpered slightly nodding while trying to get over the pain. He cuddled me and patted my head and helped me calm down. Then I threw my arms around him and asked him to try again. This time, he went in slowly and I felt so many things together.

He picked up pace and kept fucking me the next 15 minutes and I was already orgasming. I screamed out his name and clawed his shoulder. He could not hold back anymore either witnessing my pleasure and orgasmed too. We lay panting and heaving the next few minutes.

Then he was cuddling me and kissing my forehead. As he whispered my name and kissed me, I snuggled in his chest. His dick was hard again and this time, I wanted to surprise him and try something new. I went down on him and sucked his dick. He looked at me wide eyed in wonder and panted, clenching his jaws. I kept sucking and sucking till orgasmed again mumbling “I love you.”. I knew finally, this is the day I will never regret, no matter the outcome of our relationship. I was happy that I lost my virginity to a person I knew already.

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