Losing virginity with my childhood friend -Part 2

If you haven’t read the first part, check that first. Jacob and my parents were heading to a couples retreat this weekend and Jacob had more than hinted that he wanted me to stay with him. There was the anticipation of what may happen, but I felt ready. I wanted him to touch me in the most intimate way a man can touch a woman. Having sex with your childhood friend is not a bad idea either.

We were home alone Friday night and Jacob took me over to his house. I was nervous because – the first time. But I knew that it couldn’t be anyone better than Jacob for this. As soon as we entered his room, he kissed me. His arms held me close and he just squished me against him. I could taste the mint that he had eaten when we were walking home. I begin grinding against his body and felt his boner rise and prod me. I liked that he was aroused by me and liked me this way.

“Here, touch me here,” he said and put my hands on his rigid cock. He pressed it over my hand and I followed his lead, gently pressing it. He unzipped his pants impatiently and pulled them down with his boxers. Now I could actually see his cock. I lick my lips, looking at it, not knowing what to do. He again takes the lead and put my hands on his cock. It was velvety and warm, as I slowly stroked it. It twitched every time I caressed and Jacob laughed looking at my face. I was awed, it almost had a wish of its own. Jacob was still and this guy was just twitching and moving.

I held the cock with both hands and started to massage it. Jacob then took me and sat down on the bed. He sat lazily and let me play with his cock, get to know it.  I had watched porn enough times to know that the next step is probably me sucking his cock. So, I did that. I sucked the tip hard and heard Jacob moan. He stopped me. “Not that hard, gently,” he said. So, I suck on his cock head gently, slowly. I see Jacob’s eyes close and his head falls back. I must be doing something right.

I put my tongue inside the opening of his head and swirl it around. I hear him groan and his breathing intensifies. I press and rub the length up and down. He stills and then stops me. He pulls me up and makes me lie down on the bed. He takes off my shirt and just cuddles for a bit. His mouth meets mine; we are kissing and I can feel his hands caressing my bra covered boobs. “I want to see those curves of yours,” he tells me. “Yes,” I reply. He expertly unhooks my bra and removes the cups. He takes both boobs in his hands and caresses them with his thumbs.

It feels unreal, but I enjoy it as his tongue sticks out and licks both my nipples alternatively. He suckles on one like a baby and I am surprised. I didn’t know sucking one’s nipple could produce such an effect. He was horny, and his hips were undulating. I think he was rubbing himself against the mattress. He sucks some more and he caresses my belly. He removes my panties and just rubs me over my vulva. My legs close up. “Relax, relax,” he says and parts my folds.

He gently rubs me down there and I begin to enjoy it. Then he moves down and licks my clit with his tongue. I shiver at that intimate touch, loving what he is doing. I need to remember to ask him how he knows this. He licks and presses down on my clit and then sucks on the nub. It is like he is making out with my vertical lips. But yes, he does that. Then I feel his tongue circling my pussy opening. He fingers the opening and then very gently adds one finger. It is quite comfortable and it doesn’t hurt. In fact, it’s quite pleasurable. He rotates his finger inside my pussy and manages to make me super wet.

“You are so wet,” he exclaims and kisses my clit hard. He adds another finger and moves them in and out of my vagina. “Oooff, ahhh,” I go off in pleasure and he chuckles. He knows this stuff well. He stops and crawls up to kiss me. “Are you going to put your cock in here?” I ask nervously. “Yes, don’t worry, I will try to make it good for you,” he tells me. I chew my lips as he looks at me and he just stops me by kissing me. His lips meet mine and our tongues tangled. I hold him close and feel his body. Sometime during this moment, he has undressed. He sits on his haunches and rubs his cock. He wears a condom and then adds some lube to it too. “I am trying to make this easier on you Emmy,” he says.

He inserts the cockhead slowly into my vagina. It doesn’t go in easily but he moves a tiny inch in and then out and then in and out. Inch by inch he has the whole head inside. My pussy is stretching, there is some discomfort. “Emmy, I need you to relax ok. Relax, breathe,” he distracts me by rubbing my nipples and when I focus there, I feel him thrust in all the way through. I moan in some pain and he stops. He lies over me holding me, kissing my face and lips. Once I feel better, I tell him to move again.

He holds himself up on his elbows and begins moving again. His whole body is touching mine, moving against my skin. It is so erotic and I don’t feel pain anymore. I feel a lot of pleasure. His cock is stretching my pussy and I feel full. He keeps kissing my neck and touching my nose with his. We kiss and kiss, going breathless. My pussy is comfortable with his cock now. He stops and withdraws. Then he grins and stands, lifting my legs and resting them on his shoulders. He penetrates me again, making me go, “Ahh!”

He thrusts and it feels like he has gone deeper. It is touching my inner walls and his cock is almost massaging me from inside. He plumps my breasts with both hands as he moves. I can see that he is straining. He sees me looking at him and he locks eyes with me. Leaving my breasts, he starts to play with my clit. He is rubbing it gently and I feel something toe-curling. He keeps at it, rubbing and massaging. I cum, it is my first penetrative orgasm and I know that my pussy is convulsing. I see Jacob close his eyes and he releases his semen. He stops and pulls out. We cuddle for a bit and he kisses me so many times. Then he gets a warm towel, cleans me up and we snuggle and sleep.

That weekend was amazing in so many ways. Jacob made me feel like a princess; doing little things for me during the day and at night he fucked my brains out. I loved both these things so much and we became a couple that summer.

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