Despite my profile message, here’s an experience that did result in my having intercourse … technically. It was early 2001; I was 23. I was living in the Chicago suburbs with my folks saving money after college. My buddies and I would regularly carpool down to the city on weekends and go to bars and clubs. One night we went to a brewery/restaurant and met three women 2-3 years younger than us. They were visiting from Ohio and staying at a Homewood Suites around the corner from the brewery.
We ended up going to their hotel and hanging out in the hospitality suite on their floor. I was really hitting it off with Sara, a doe-eyed beauty, standing about 5’6″, far and away the best looking one of the three. If it were the other way around and one of my buddies was hitting it off with Sara, I certainly wouldn’t have blamed at getting to know either of the other two, but my friends were not as flexible.
I was the driver that night and nothing was doing with my friends and Sara’s friends, so I had to drive my buddies back to the suburbs. Before I left, I pulled Sara aside and asked if it would be alright if I came back after driving them home. Sara said, “Yeah, if you want to go all that way.” My friends couldn’t believe I was going to do this, but I said, “Even if we just kiss, I want to lay the groundwork with this girl. She’s hot.”
Maybe an hour, hour and 15 minutes, I was back at the Homewood Suites. Sara changed into a T-shirt and sweat pants and let me into her hotel room. Her other two friends were asleep (or pretending to be asleep) on a full bed – the only bed – in the room.
Since there was a not much of an opportunity to talk without waking her friends, it made it easy to make a move. I kissed Sara and it was well received. We kissed. She did not have a bra on beneath her T-shirt; I fondled her breasts. Very soft but perky. Because we couldn’t ‘get into it’ with reckless abandon due to her friends being on the bed, Sara started getting tired.
She yawned and said, “Don’t be offended if I fall asleep; it’s not that I’m not having fun.”
I told her I understood, and, though it wasn’t my practice to verbally ask permission at each successive stage of a hook-up, I really wanted to feel her vagina so I whispered, “Do you mind if I finger you?”
She whispered back, “Sure, but I can’t really do anything for you if I fall asleep.”
I replied, “Don’t worry about that. Getting to touch you down there is pleasure enough for me.”
With that, I slid my hand down the front of her sweat pants and panties. If my fingers were any judge it seemed Sara kept the natural triangle of her pubic hair but she clipped the length shorter, which for 2001 was a treat since so many beavers were completely shaved! I located her clitorus and flicked it with my finger and then probed her opening. I easily slid one finger inside of her and to my delight, felt her vagina lubricate. I inserted a second finger in her vagina, wiggled them around a little. Sara was asleep at this point, but when I would massage her vagina, her breathing would quicken, so I took comfort in the idea that she was having sweet dreams. At one point because she and the rest of her crew were asleep I was able to remove my fingers and take a whiff. Her vagina literally smelled like a bar of soap! In fact, I had no doubt she took a shower, to at least wash her vagina, between my earlier departure and my arriving back. I thought that was really flattering. I returned my fingers to her warm, wet vagina and fingered her all night long until the sun came up. When it did, we kissed goodbye. I got her phone number and AOL address, and parted ways.
In the weeks that followed, I kept in touch with Sara. We especially used AOL chatting to talk to one another.
The first time we chatted, I typed, “By the way, I owe you an apology for the night we spent together in Chicago.”
She replied, “Oh my G-d, we didn’t, did we?”
Sara thought I had sex with her – apparently she drank a lot that night! “No, we didn’t do that. I was just going to say sorry that I fingered you all night. Might’ve been a little invasive of me.”
Sara used the nascent term “lol,” and said, “Oh that? I don’t care about that. I’m sorry I was asleep and couldn’t do anything back to you.”
Admittedly, my ‘apology’ was disingenuous: I just wanted to get the conversation in a sexual direction. It worked and I said, “That’s no problem. I’m sure you can make it up to me when we see each other again … ” Sara took the bait and said, “Are you interested in visiting Columbus?” I was!
That April, I was on a plane headed for Columbus, Ohio, looking to get laid. I had asked Sara where a nice place to eat in Columbus was. She suggested a converted church called The Refectory. I made a reservation there for the night I arrived in town. Sara was wearing a sleeveless blouse and short skirt that really showed off the curviness of her hips and ass.
We had good food, and a delightful evening. In the parking lot, we started kissing. It was passionate. Sara interrupted our kissing to say, “I feel so bad. I’m on my period.” I didn’t mind and told her so. We returned to her home. Sara technically lived with her parents, but she lived in a rural town outside of Columbus on a large piece of property. She lived in a small one bedroom guesthouse. So it served as the perfect ‘fuck pad.’
We resumed hooking up, and started undressing in her bed. I took off her panties and sure enough noticed the telltale string hanging from her nest of mousy brown pubic hair. As I had speculated, Sara had a natural triangle of bush, but the length was clipped not overly short, but more shorn than what G-d gave her. I asked her if I could lick her clit if I left her tampon in. She said, “I guess if you really want to.” I did. I licked her clit and this time, her pussy didn’t have that same soapy smell. It smelled faintly like period. Not awful, but if you missed the tampon string, you could tell she was menstruating from the odor. She didn’t let me lick her clit very long. I rarely asked for sexual favors, but in our chats and phone conversations, she had told me that she had been complimented on her ability to give guys head.
I was fully nude at this time so I brashly said, “I really want to experience your blow job skills I heard about.”
Sara laughed, and said, “I guess I set myself up for that.”
Sara proceeded to put my erection in her mouth, bobbed down on it, and I distinctly remember seeing her lips make contact with my pubic hair. She demonstrated she could deep throat a 7 inch erection, that was proof enough for her.
She took my penis out of her mouth and moaned, “What are we gonna’ do?”
I took this as her looking for permission to have sex on her period, so I said, “We’re going to have sex.”
Sara went to the bathroom to discard her tampon. I got a condom out of my pants pocket and started putting it on. I never had any luck with condoms up to this point. Invariably, I would lose my erection either in the process of putting it on or once I tried to penetrate. Sara assumed the doggy style position which I thought was pretty hot. I got a great view of her ass revealing her butt cheeks to be of the long lobe variety. Really quite breathtaking. Her labia minora were reddish maroon, but actually closer to red. Her opening was pronounced and inviting. Despite my condom problems I was able to penetrate Sara and, boom, we’re fucking.
The problem was Sara was not just on her period. This had to have been her heaviest flow day. I’m going to spare all of you the graphic description. Suffice it to say, there was a lot of menstrual blood. I thought I could power through it, but it was just so messy that my erection started to flag. Had I been bare-backing, that wouldn’t have happened, but I was trying to be safe, and the period coupled with the condom, I went soft. We tried two more times with two more condoms, but to no avail.
I still really wanted to orgasm so in the spirit of open communication I had established with Sara in the short time we had known each other I actually said, “I really want to cum, would you mind giving me a hand job or a blow job?”
Sara obliged and asked, “Is a hand job okay?”
“Sure.”
Sara jerked me off. It didn’t take long and I orgasmed. I remember that even though some might consider it anticlimactic, it was actually a pretty intense climax. When my semen started spurting out Sara let go of my penis. I ejaculated hands free on my abdomen and said, “Thank you, that was a great hand job.” Sara giggled and said, “You’re welcome.” I offered to eat her out around the string if she wanted to put in a new tampon, but she was too shy for that. Still, we had a nice two days together and it was a worthwhile trip for both of us.
Source: reddit.com/r/gonewildstories/comments/lznbzz/meeting_a_f_visiting_my_hometown_with_her_friends