[Link](https://www.reddit.com/r/gonewildstories/comments/6iky2i/losing_my_virginity_to_the_beautiful_girl_from/?st=j4d8zy4y&sh=1aa0ab0a) to original post.
I apologize if this doesn’t seem worthy of a new post, since it won’t contain a very full, well-written story. I considered just including an update in the comments of the first post, but figured few people would see it.
My first post got a much better response than I would have expected. It was obviously a great experience for me, but I hadn’t realized it would resonate with people as much as it seemed to. It was especially awesome to have quite a few people say that the story of my weight loss had helped inspire them. I had considered not really including my weight loss, or much backstory, so I’m glad it was apparently good that I did.
A number of people asked me to write about the experience I had with the second girl. I had planned to, and had actually started writing it, but wasn’t feeling it as much as I’d have liked, in part, I think, because I have some regret about the experience. What made the first story so fun and enjoyable to write about was being able to relive what was such an amazing experience for me. I really got into it, remembering details and feelings, which is probably why it ended up so long. Writing about the second time, while it was a fun experience and enjoyable at the time, doesn’t elicit the same feelings, again, probably because I kind of regret it. The reason for that is that even though Mandy had insisted that she thought I should try to have experiences with other girls, and though I had believed her, I now wish I had just told her that whether she wanted to date now or not, I would only be sleeping with her.
Although I decided not to write a full-on story about that second experience, like with my first story, I will write a brief recap for those who were interested. I’ll probably be writing more about the backstory than the sex itself, so I apologize in advance. I’m writing this more for those who were curious than for the purpose of entertainment, to be honest. After the recap, I’ll include an update on how things are going.
The second girl is a girl I knew from her place of work. I would see her often and talk to her, and we got along well. She was actually probably the one girl that I was attracted to that I believed I had a shot with, but even believing that, I didn’t have the confidence to act. She got engaged a few months ago, but I learned, from a friend who works with her, that her and her fiancé had agreed to let each other sleep with other people up until the wedding. Then after my experience with Mandy, I suddenly had some confidence, as well as her insistence that I try being with other girls. I felt iffy about being with an engaged girl, but also liked the idea that there wasn’t a chance of it becoming something more and messing things up with Mandy. So I decided to try to make it happen. In short, the next time I saw her I talked about how her fiancé was a lucky guy and how I guess I’d missed my chance. She basically told me that that wasn’t necessarily entirely true, and to call her after work.
When I called her she explained her situation with her fiancé, told me she’d always thought I was cute and funny, and said if I wanted we could hang out and see how things went. I told her that sounded good to me, but, while I didn’t want her to think I didn’t believe her, I asked if I could talk to her fiancé to make sure it really was ok with him. So she gave me his number, and I called and confirmed that it was fine. She told me that she wasn’t just going to come over and have sex, but that I could basically make it a date, and if it went well we could see where it went. I actually thought that sounded fun and invited her to my apartment and told her I’d make her dinner, since I love cooking.
I guess I should give a quick description of what she looks like. She’s got dark red hair. She’s the type of redhead that I don’t realize is a redhead right away, kind of like Kate Mara. Her face is best described as cute, not referring to her level of attractiveness, but rather her type of attractiveness. She has a nose piercing that contrasts nicely with her cuteness. She’s a pretty average height, probably around 5’5″. As a body comparison, I think [this girl’s](https://gfycat.com/PerfectGiddyAmericanbadger) (NSFW Link) is similar (Not the best view, but hope it gives some idea). She’s got a pretty soft, natural body. It’s not the toned, gym body that Mandy has, but definitely cute in its own way. I’d later learn she has a belly button piercing, as well as pierced nipples, on what are probably a-cup boobs. She also has a tattoo down her side.
So I had her over and I made her dinner. We dressed fairly nice and made it like a semi-romantic date, because she wanted to. It was honestly pretty fun. It was strangely stress-free, I think because I wasn’t at all worried about it and figured whatever would happen would happen. I wanted it to go well, but if it didn’t, I really wouldn’t be too upset. We got along as well as ever, and it was pretty clear it was going well enough for us to have sex. It’s also strange how little nervousness I felt about the sex itself. I think the combination of the confidence I’d gained with Mandy and the knowledge that this wasn’t going anywhere made me pretty relaxed about it. In fact, the next time I was with Mandy I was quite a bit more nervous than this night, because I care so much about how things go with her.
As we wrapped up dinner and dessert she just went ahead and told me that she wanted to have sex if I did. I obviously did at the time.
So we went to my bedroom and undressed each other as we kissed. The foreplay was much shorter than when I had been with Mandy, which was how this girl seemed to want it. That also meant that the sex was much shorter. She actually had me watch her masturbate on the bed as part of foreplay, which was interesting, but pretty hot. After that she pretty much wanted to just get to the sex, and I ate her out for only a minute or so before she was telling me to “fuck” her. The personality I’d gotten to know wasn’t that of a girl who I would expect to hear saying “fuck me”, which made that pretty hot. I wanted to try different positions than I’d done with Mandy, so I had her get on top at first. After she rode me for a couple minutes, I had her get off and I kissed and fingered her. Again, she was saying “fuck me” after very little time. I had been disappointed to not be able to try doggy with Mandy, so I got behind her and tried it with her. She asked me to slap her ass a couple times, and I think my lack of enthusiasm in doing so disappointed her a bit, but I didn’t want to do it too hard. There was one more position I wanted to try, so after a minute I grabbed a pillow and slid it under her hips, then asked her to lie on her stomach. What I’ve read says this “prone bone” position feels good for the girl, and makes the guy feel bigger inside her, which is an awesome plus if true. While I was on top of her like this she managed to shove her hand in between her and the pillow/bed and was rubbing her clit, and I am pretty sure she came like this. It wasn’t very long after that until I came, just in the condom.
From start to finish I don’t think the sex lasted much more than ten minutes. It was definitely more hurried and intense than with Mandy, which was fun to experience. Overall I definitely felt I had preferred the slower, more tender style with Mandy though. One thing I had been pleased about this second time was my stamina. Even though it was much shorter overall, it was mostly PIV, more total PIV than with Mandy, and I felt pretty decent control. I definitely felt that I could have kept going, but let myself cum when I did.
It was a fun experience, but as I mentioned before, I regret it happening now. Mandy had been sincere, I believe, when she insisted on me sleeping with other girls, but that doesn’t mean I had to. At the time I was kind of riding the high of my first sexual experience, and the confidence that came with it, and I was excited to “make up for lost time”. It didn’t seem to ultimately affect things negatively with Mandy, but I still wish I would have made the gesture of telling her I wasn’t going to sleep with anyone else. A couple days after being with the second girl, soon after my second time with Mandy, I decided that “making up for lost time” by being with other girls wasn’t what I wanted. So this past week I hung out with Mandy and decided to talk to her about it all. I told her I was happy to be FWB’s if she wanted, but that I wasn’t going to pursue anything else with other girls, and would love to try dating if she were ever open to it. We actually had a really good talk, which I won’t really get into. The bullet points are that she had felt like it wouldn’t be fair to not encourage me to “sew my wild oats” a bit after being a virgin for so long, and that she was very interested in trying out dating, but wanted to kind of take things slow dating-wise (And no, the irony wasn’t lost on either of us that we had had sex the first time we hung out, and were talking about “taking things slowly”, and we laughed about that). She has her reasons for wanting to not jump into dating too fast, and I absolutely understand and respect them. Fortunately, starting our dating slowly wasn’t to affect the sex having.
So far, things are going absolutely as well as I could have hoped for. She’s seriously awesome, and I still don’t understand what she sees in me, but I am not complaining.
I appreciate the interest some have expressed in reading more about my sexual experiences with Mandy, but honestly, it is my great hope that they will continue to happen far too frequently for me to write about them. However, if anything especially noteworthy, or out of the ordinary, happens, I may write about it. For now, I am going to continue to enjoy the very pleasant, unexpected turn my life has taken.
Sincerely, thanks to all those who have expressed well-wishes, as well as those who have complimented my weight loss and everything. I’m genuinely blown away by the response to my story. So thank you all!
Source: reddit.com/r/gonewildstories/comments/6kcu36/update_losing_my_virginity_to_the_beautiful_girl
That’s awesome man, I hope things continue to work out & ramp up!
It’s hard not to act like the cat that got the cream when you get that ego boost and the endorphins are racing through your system :-) You did the right thing, I think. Just need to take it easy with Mandy. Give her time. Enjoy.
This was sweet. I’d forgotten about the original post but I stumbled across this while going down my Reddit feed just now.
I’m glad you wrote the update and that I was able to catch it :) Wishing the best for both of you
Good followup story, good confidence boost and ability to discern what you do and maybe do not want. There’s a campy Dracula movie from the 70’s/80’s with George Hamilton as Drac, wherein he has a line “Vit you, never a qvickie, alvays a longie”. Something to ponder…
I don’t know your workout regimen, but add some running or bicycling to help keep your cardio stamina high if you don’t already.
Each woman is unique and different in how they regard their own ability, their desires to either please or be pleased, and I have found (being an older male) most like or perhaps, respond well to a decisive, confident male partner with stamina and the ability to go for longer periods of pleasure. This sounds stupid, but when you can assure them of a 10:1 big “O” evening and you are in charge of it and do in fact produce that or close to those numbers, the world is yours for the taking.
Also, enjoy playing a carefully select field, not falling or becoming too possessive or a man slut, nor allow same from their POV. That’s point of view, not penis out of vag, altho’ that too is a great technique to master (think lap dance naked stimulating clitoris with erection)…
As to spanking… every woman should have her sweet bum spanked smartly once in a while.
Awesome tale of your transition so far. Keep working out, continue learning about and giving more pleasure than you receive… and it would do you well to master the art of massage (as a beneficial hobby to anyone who works out and loves to rub the female body and listen to moans of pleasure. Practice on Mandy initially)
A young man who has done what you have done mastering your weight, self control with discipline, should be confident in not yet knowing what he has yet to learn, (we don’t know what we don’t know) but eager to learn, and to give to others.
Thank you for the gift of this story to date. You do write well. Carry on.
Heterosexual dude here. You come across as such a sweetheart in these stories.
I think the latest be looming has actually made you into a better person who’s respectful and mature. Kudos!
Oh thank god you and Mandy are going to date. I was about to write a nasty comment after reading your original post. As another heterosexual man, I have to say you are very sweet and romantic it seems. I enjoyed reading how tender you were with Mandy in the first post.
I hope this has a happy ending and I think I speak for everyone here when I say we are all rooting for you and Mandy.