I met Olivia in one of my college media classes. She was about 5-foot-4, long brunette hair, brown eyes, average-to slender, C-cups that she normally wore in a halter top over blue jeans shorts and sandals. Cute legs, nice ass, a typical So Cal girl.
One day, I decided to ask her out. We got talking about past relationships. She guessed that I was "experienced" and I blushed, admitting that I was still a 24-year-old virgin. She was shocked. Then she admitted losing her virginity, at 16, to a "high school sweetheart." She also said it was "awkward" because she was the first of her girlfriends. They'd broken up a year earlier "And I haven't been laid since," she admitted.
I asked Olivia out on a date and she, politely, declined. "Another guy, Micah, asked me to go to his beach house, in Mexico, this weekend," she explained. "I agreed. I'm nervous about the sex, though. He's had a few partners."
I sighed, in disappointment.
"What's wrong?" Olivia asked.
"I like you," I responded. "You could have been my first."
"Really?" Olivia giggled. "You would have given it to me? That's an honor. Look, I don't want to date with this other guy in the picture. But I am out-of-practice, nervous about sleeping with someone so experienced, and don't want to disappoint him. Would you like to get together for some fun?" she asked.
"Are you offering to take my virginity? I asked.
"Why not?" Olivia responded. "It would be fun, no strings attached, and we can hook up, more, later if the Mexico guy doesn't work out."
"When? I need to buy condoms," I said.
"I hate those things," Olivia said. "I am on the pill. I prefer bareback. There is a hotel a block from here. I'll buy. This is my gift to you."
We started walking, hand-in-hand and 30 minutes later were checking in. Soon we were at our room, kissing, and undressing each other. Olivia wasn't wearing a bra, our shorts and undies hit the floor, I was enjoying licking and kissing her nipples and stroking her sex. Olivia has a, beautiful, hairy pussy, and, soon I was on my knees worshipping her clit. We moved to the bed, enjoyed a 69 (her on top) and, I nearly, reached a climax, (while she orgasmed) before we flipped over, preparing for the main event. I wanted to wait to cum inside Olivia.
Missionary style, I slid into Olivia and she instantly orgasmed. "Sorry, it's been awhile," she said.
"Better you than me, for a quick cum," I joked.
"This is true," she said.
We started a slow rhythm, kissing and me licking and kissing her breasts. The tit-worship gave Olivia another orgasm. "Wow," she said. "I never had multiples before. You're good!"
I laughed and stopped thrusting to hold her until she was ready to continue. A few minutes later, she started moving again and we continued having sex. I re-started kissing her lips and breasts and started to feel my cum making its way while she started another orgasm. We screamed and held on as we climaxed together...
We held each other for a few minutes then I rolled off and we cuddled.
"Wow, that was fun," she said. "How was your first time?"
"Wonderful," I responded. "If you give me a few minutes, we can go again."
"Deal," she said. "Let's break in the Jacuzzi and shower."
We spent the evening, tenderly having sex, spent the night, and woke up in more passion. We walked back to campus and said goodbye. "Don't forget about me, in Mexico," I suggested.
"I don't think I will forget you," Olivia said, "But I promised him the weekend. I will see you in class and we can talk after."
The next week, Olivia stopped by my table in the quad. "How was Mexico?" I asked.
"It was OK," she responded. "We started having sex, Friday night, but an hour later, my period started. The good news is that neither of you need to buy diapers. The bad news is that he acted like I was dirty and wouldn't even kiss me anymore. I don't need that scene and had him drive me home in the morning. I made him sleep on his sofa. We're both pissed at each other. He's history."
"I am sorry that he treated you that way," I said, hugging and kissing her. "You aren't dirty or damaged. Periods are, a rough part, of being a woman. I get that."
"Thank you," Olivia responded. "For a newly-former virgin, you're a sensitive guy. Thank you. Now, considering everything that's happened, including me screwing Micah, do you still want to date me?"
"Absolutely," I responded. "You were up-front about Micah before we had sex. You're up-front, now. You're a cute, intelligent, sexy woman with a great body that's great in bed and the shower and Jacuzzi. As long as you and I agree that we are exclusive, I want to date and sleep with you."
"Great!" Olivia said. "Micah also insisted on a damned rubber, so I am still clean. Want to go to lunch? I'll buy. There's a sub shop between here and the hotel."
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