Nov 012015
 

So, we were dating for a year and we often talked about our first time but it never happened because he was never at my house and i was never at his house. It was the first time I came to his house, we watched a movie and made out. We became horny and he asked me if I was okay with that so we did it. I regret nothing, he was gentle and sweet and it didn’t hurt that much.

  • Name: Lucy
  • Gender: Female
  • Age of Virginity Loss: 16
  • Current Age: 16
  • How would you categorize your story?: Loving
  • Country: Sweden
Oct 192015
 

They called me “A-V” when I was a teen; it was a take off on “Averell Harriman” who inherited the Union Pacific railroad from his dad when he was like, 18 years old, or so. My dad worked for a state university in town. Let me back up. In the sixth grade I read an autobiography of a family who were sailing the islands, home-schooling their kids as they went. This was long before “home schooling” became as popular as it is today. The idea intrigued me, since I hated the school experience I was having but loved to read and learn. I investigated the requirements for home schooling and how to get a degree through correspondence. It took a lot of work and getting my mother to meet with the county school guidance counselor to convince her (my mom) that what I wanted to do was legal and official. Mom really didn’t have to do much but send a letter to the state or county each year letting them know how i was being educated. I also found out that since my dad worked for the state college in town, I was eligible to take courses there tuition free. To make a longer story short, I was ambitious and finished high school early while simultaneously taking classroom courses at Mary Washington and correspondence courses through the University of Maryland. I finished college at 18. What i did not expect, initially, was that once I was solely focused on finishing my BA, it gave me a lot more free time than I had attending public school. (You know, on the bus at 730am and off the bus at 345pm). Because I went with my dad to work 2-3 days a week depending on my course schedule for that semester, I was able to finish my homework on campus and also get a part-time job. Then enter (well, I guess it was really an exit) my grandfather, who, unexpectedly bequeathed me a small inheritance when i was 15. It did not make me independently wealthy, but it provided enough for me to set myself up in a small business when I was 17. We petitioned the court to grant me my majority so I could run the business without having to have my parent’s signatures on everything. It was a charmed life. What happened, however, was that I invested my time in my business and investing, getting a pilot’s license, and flipping some commercial real estate; I did not invest any time in relationships. So, at 19 I was making a bundle, giving away a lot of it to local charities anonymously, driving a used Porsche 912 and rebuilding a Cessna 180, and I was still a virgin. I was not nerdy, I was athletic and all, but I had zero sex-perience with anyone. Then came Patty. Patty and I met in college. It was a predominantly girl’s college, and everyone on campus knew my dad and knew I was 14 when I started taking classes, therefore I had no chances of getting laid. I was treated like a younger brother, which was appropriate. Nevertheless, my 14-15 year old hormones raged incessantly in the midst of 18-22 year old women. The girls that were appropriate for me to date, aged 15-18, fell into two categories: (A) their parents would not allow them to date me since I was a “ college man” and (B) gals that I did not want to do anything with since they seemed so “young”. This was in the early to mid seventies. I was one frustrated dude, but also a driven dude to finish school, convincing myself that one of these days “IT” would happen. Patty and I met, interestingly enough, one day in the library. We were not in the same circles, but one day in the library I was sitting nearby and it became obvious that she was frustrated with something she was working on. At the time, I was in my senior year and she was a junior. (I was 17, she was 20) She was struggling in a math class that I had already taken and I offered to help her. We spent the afternoon going over her homework and became “friends” as a result. Our paths continued to cross over the course of the year, she got a job at a coffee shop I studied in off-campus. But there was still that 17, 20 age thing going on. The summer after graduation I decided to buy a condo in Hilton Head (HHI) , SC. That was a function of how far I could fly my Cessna on one tank of fuel. If I had more range and speed, I would have preferred the gulf coast of Florida, but Hilton Head was as far as I could go on my fuel plus reserves. Additionally, I decided to set up a storage rental facility in the Hilton Head area to have a tax reason to fly down there. Patty was working at the coffee shop that summer before her senior year. In conversation, she asked what I was up to and I explained that the following week I was going down to Hilton Head and spending a week, closing on the occupancy permits and hiring staff for the storage site. She begged to go with me. I thought she was just making conversation, especially since I noticed a small engagement ring on her finger, but I treated it as though she was serious and told her she was welcome to come down but that for the first part of the week I would basically be tied up working. She vacillated for a few moments and said that she could take herself off the schedule for most of that week and could get a sub for the other 2 days; she would love to have a week or more at the beach to relax. We set it up. Saturday morning she met me at the small airport outside town, I preflighted the plane, got the weather forecast and off we went. We landed about 3 hours later. I called a cab to take us to my condo, which from the HHI airport was only a 5-10 minute ride. There I kept a used Jeep. I set her up, while she protested, in the master suite and I took the guest room with adjoining bath. We went out to the supermarket and got enough fresh food for a few days and stuff for me to take for lunches. I showed her the path to the beach and helped her pack the little cart to tug it to the shore. She looked good in her swim suit! Patty had brown, shoulder length hair, brown eyes, nice legs, nice boobs, though, forensically speaking, her hips were just a tad wider than what I considered perfect at the time. She seemed cognizant of that and it wasn’t until I saw her in her suit that I noticed, since heretofore the way she dressed had hidden hid that insignificant attribute. True to my word I was basically tied up all day Sunday finalizing the site preparations and meeting with the manager I had hired. I asked if wanted to take the Jeep the next day and she said no, she did not know how to drive a manual transmission. I offered to teach her then and there. She agreed and learned quickly, HHI being rather flat, and within an hour she was capable of driving it herself. The only thing she had to remember was that if the Jeep started “bucking” to put in the clutch and start again. I suggested that on Monday she drop me off at the Storage facility and keep the jeep, I’d let her know when I was done. She agreed. We did this schedule Monday and Tuesday and by Tuesday evening I was done everything I needed to do. The city permits would not be signed until Monday so there was no way to have our opening until the following week. I am an early riser so on Wednesday I was up at 630am; Patty slept in til roughly 900am. For the past two days she had been out to the local shoppes and artisan places, which I had already seen. We both decided to hit the beach. That worked for a couple of hours, but then it got really hot and I could tell from the wind shift that we were in for a rain storm soon. We went back to the condo, showered, changed and elected to eat out. We had a nice lunch, and then came back to the condo. Up to this point we really had not spent too much time together. But that afternoon we had a blast talking and playing some board games. She did talk about her ring. Her “fiancé’ was in an ROTC program and gone for most of the summer. They were affianced without a set day for a ceremony. I realized she was a really nice girl, an intellectual equal, a valuable friend, she treated me as a peer and she was quite attractive. I was torn between wanting to pursue her and feeling that her engagement ring was a barrier of sorts. I admit i was a bit old fashioned by many standards. But at the same time, I noticed she had ramped up her flirting. That evening, after dinner and clean up, we agreed to walk the beach. In was dark and there was almost a chilly sea breeze, which at that time in the summer was a real treat. We were having a lot of fun talking and getting to know each other better. I brought up the name of her finance a couple times but each time she seemed to deflect talking about him or considering if he would approve of her spending a week on the beach with me. It was one of those things that happens. We had gotten to the turnaround point of our walk and as we turned she mentioned that she was feeling chilled. Without hesitation I unbuttoned my Hawaiian shirt and put it on her. After she thanked me it seemed as though her mood changed and she quieted down for a few moments. She paused and turned towards me. I faced her and she lifted her hands to gently frame my face and pull my face to hers and our lips met for a long kiss. After our lips parted we stood there hugging each other. I let out a breath and just said, “Wow!” I barely heard her, her face against my chest, say the same thing. She then looked up at me and in all seriousness said something like, “Dave, you treat me so nicely. But from what I’ve seen you are a gentleman with everyone.” Then she simply finished with, “Thank you.” I mumbled out something like, “You make it so easy for me…” We broke our embrace with a quick lip-to-lip kiss, and turned to continue our stroll. My thoughts were racing, my heart was pounding and yes, my manhood was stirring, big-time! We took maybe five steps and I reached my hand out until hers brushed against it. Her fingers curled in mine and we walked that way with her other hand on my arm. We climbed the wooded boardwalk towards my condo. When we reached the far steps by the parking lot, she paused once more. We faced each other and she put her hands on my bare chest (it felt absolutely electric!) looked me in the eyes and asked if we could had to sleep in separate rooms tonight. I answered immediately, “No, we don’t!” Then my memory caught up with me and I thought things through. I was a virgin, I had no experience; I was betting she did. I held her to me and then hoping I was not going to blow a sure thing…. (I don’t want that to sound calloused, I really did not look at her that way, I just really enjoyed her in all aspects and did not want to do anything that might jeopardize our relationship as it was…well, plus, I really wanted her to be the “first”)… I said, “Patty, can we talk?” The way I said it she suspected something was up. She immediately said, yes, we can, and asked if there was a problem. I assured her that it wasn’t so much a problem as it was a situation. I paused again to take a deep breath and to hold down the tears I felt welling up. She was perceptive and could even tell from the way I took in my breath that I was struggling to tell her something profound. She said, “Dave, whatever it is, its ok…” Then she added, “ is it about Ray?” (Her fiancé) I shook my head, “no” and held up a finger to tell her to give me a minute. She nodded assent. I noticed a singular table and chairs out by the tennis courts, pointed to it and led her there. We sat down. It took me a moment to gather my thoughts. My voice broke momentarily as I started but then I was able to suck it up and get it out. It went something like this, “Patty, I am really fond of you and I adore our friendship. I don’t want to do anything to jeopardize that. You know I had a kinda unusual teen experience. I have invested a lot of time and energy into what I think are some really cool things. I got the education I wanted at a young age but at so young an age that I missed some of the things guys do, that are of regular college age, so there are some areas in my life where I feel I am at a deficit, experience-wise. Intimacy of the type that is implied by sharing a bed is one of them. I’m a virgin, and I am sure a clumsy one at that.” I had not been able to make eye-contact with her until my last sentence. I then looked her in the eyes. She put a hand to my face and was compassionate. She stood up slowly and (I thought she might walk off, I was so confused) got closer to me and held my head against her breast and kissed my head. She said something like, “Dave… I am so glad you chose transparency and shared that with me now, before we go back to your place. I imagine that took a lot of courage. Honey, your experiences, sexually, up to this point aren’t a concern for me. I really enjoy your company, too, and our relationship, and this moment. Likewise, I do not want to do anything to jeopardize our friendship and relationship or any personal commitments you may have about who you want to have that first intimate experience with.” I stood up and held her closely and I told her I could not talk yet, but to just wait a min. I then said something like, “Patty, I didn’t conspire to bring you down here for any purpose than to give you a vacation and enjoy your company. My only personal commitment was to wait for someone mature and for whom I had strong feelings. (She interjected at that point, playfully, “Well, I guess you were unaware that there were at least two girls on my dorm floor who would have been happy to give you that first experience when you were 15!” We both laughed it off.) That broke the seriousness of the moment. I held her and she leaned back against my arms and looked into my eyes, smiled and said, “So, where are we?” I took a deep breath and answered, “We are on the beach at HHI, on our way back to my place, where I hope my dear friend will teach me patience and what I need to do to be a sensitive lover.” She smiled, shook her head and told me I seems to have the sensitivity stuff down already. We strolled slowly to my place where I had trouble, with shaking hands, getting the key into the lock of the front door…

  • Name: Dave
  • Gender: Male
  • Age of Virginity Loss: 18
  • Current Age: 59
  • How would you categorize your story?: Loving
  • Country: USA
Oct 122015
 

He is my Dream. I met him while working for same company in my college day. He was cute and tall. we went out for first time and we kissed. After few day my mom went out, i call him up my house. I kissed him straight way he entered in. He picked me up and took me to on sofa. He removed my all cloths and moving hands all over my body. i hold his penis and start rubbing. soon it was hard as rock. he start moving his penis on my vagina. I asked him to pushed in bcoz i already had orgasm. He fix me up and placed penis straight on my vagina hole. He pushed in, i hold him tight and screamed. He pushed again and i could feel his tip inside me and pain which made me drop tears. soon he entered full in me and i could feel bones cracking inside me. I asked him is he full in he replied no. i asked him to go full in but slowly..so he did. He take out his penis and changed position . i m laying on sofa n he was standing he pushed in again and starting going slowly. mean while he was pumping i start feeling i has reached orgasm again, he was keep going and increased speed as well. he took lil rest and start fucking me again but this time he was rough. i was in hell of pain but with time i start feeling good. he cum inside me and i reached my 3 orgasm meanwhile. to make him feel special i want to suck him but his penis was wide so i couldnt fit in mouth.

  • Gender: Female
  • Age of Virginity Loss: 20
  • Current Age: 21
  • How would you categorize your story?: Loving
  • Country: Australia

 

Oct 122015
 

Now to start I want to make clear that I’ve never been really a ladies person, I’ve always found it hard to talk to them and then to try to take it further was impossible. I’ve had my odd bits and bobs around but nothing really worth bragging about. When returning from a day of college I met an old friend on the bus ‘Hazel’. I hadn’t seen her in years so I wanted to talk and catch-up. We did. We ended up talking on the bus home for at least an hour… during these talks we somehow managed to get onto the topic of sex and experiences. She had a boyfriend of about a year and she said that she has done pretty much everything and enjoyed it. I was the opposite, I’d kissed a couple girls and maybe seen boobs once or twice. So when I said that I haven’t done anything she first looked at me like. I don’t believe you or really… She then lent over and whispered in my ear. “There is always time to change that” before she kissed me on the side of the cheek and announced whilst walking to get off the bus “I’ll talk very soon” For the next couple of days I heard nothing and was a bit disappointing as I thought she was stunning and I would be lucky to do anything with her. The fact that she had a boyfriend never even crossed my mind. I got home from work a day or two later to a message of a new account with the name as ‘Heizuchan’ saying – Tomorrow… I want to meet and I want to talk about something… just talk. Meet me on the fields on the village outskirts. I did

There was a small square field on the outskirts of the village surrounded in trees and bushes. She was there just sat waiting. We met and she didn’t say anything she just grabbed my hand and took me through a bush that let to another small field completely surrounded by trees and bushes, you could see a thing. There she had laid a blanket on the floor. She Walked me over and whispered in my ear. “What’s the one thing you want most” I stuttered back “probably a blowjob.” I don’t know why, but i felt that they would feel the best. She told me to close my eyes. I did. I felt something tugging at my belt and buttons, they slid down to my ankles. Her cold hands grabbed the elastic of my boxers and pulled them down too. I was already hard with anticipation. I felt her cold hand on my shaft slowly starting to tug at it, after about thirty seconds it stopped and then I felt her. I opened my eyes and looked down, her mouth was half way down my shaft, she was doing amazing things with her tongue… flicking it, playing it around my head. It was the most amazing feeling I’ve ever had. She then took all of her clothes off, she was there on her knees completely naked. I got even harder and more turned on. She took my cock out of her mouth and wrapped her big breasts around it and started moving me… I couldn’t wait any more, I wanted to taste her. It had always been a bucket list of mine so I grabbed her hair (She told me she liked it kind of rough] and put her on the floor, working my way down her body with my lips i reached her. and I did not hold back, i licked all over kissed her thighs, and slid a finger in there whilst I was exploring her with my mouth. She pulled my head up by my hair and shouted to get in side of her. She told me she was using contraception and i believed her. I leaned forward and inserted myself into her. It was the most amazing feeling to be so close to somebody and to feel there every movement. I got fasted and deeper more passionate. I kissed and licked her nipples whilst i fucked her and she moaned quietly in my ear. She grabbed my ass cheeks, one with each hand and made me fuck her faster. It didn’t take long for me to tell her that i was going to cum. She sat up, made me slide out of her and reached down and started tugging on me again. She said “I don’t want a mess, so cum in my mouth.” That was the way i wanted to finish most so her saying that made me get to climax much faster, I stood up and without hesitation she put her mouth around my head and furiously tossed me off. I grunted the fact that i was going to cum so she sped up and put her head back. I came. Hard. But not a bit to waste. She swallowed the lot. Five minuets passed and we were both fully dressed. She took the blanket and put it under her arm. I felt the need to thank her. She said it was my pleasure. and walked off… i never heard from her again.

  • Name: Elliot
  • Gender: Male
  • Age of Virginity Loss: 17
  • Current Age: 19
  • How would you categorize your story?: Loving
  • Country: UK
Oct 122015
 

I just had sex for the first time today. My boyfriend and I were at the beach yesterday, and became very turned on while changing together in the car. We tried having sex but it ended up hurting too much and I bled a little after. We still had a great rest of the day, even after an emotional scene of feeling bad for both myself and him. Today we were alone together after his dad left the house. I said I wanted to try again. I just wanted to get it over with. It hurt a lot at first and there was a lot of fumbling with the condom, but we managed to make it work. It was weird because we decided to do it with mostly clothes on just in case anyone happened to come home, only my pants were off and his just barely. He layed me down on the edge of his bed and stayed standing. I’ll admit, at first it hurt. Then I really didnt feel much. It was probably just because of the angle and he offered to try a different position, but I was too worried I’d feel pain instead of pleasure, so we just kept going until he came.

It felt like an out of body experience. There was really no pleasure for me but he made it up to me right after until I had my release. I’m both happy and sad about it. I know it could be much worse. I had sex with my first love and someone I know is very much in love with me. But when you’re 16 you imagine your first time being magical, with a large white bed full of rose petals and a romantic song playing in the background and afterwards lots of naked cuddling. Mine was not like that. Mine was pretty rushed but I have someone who loves and respects me and thats all I could ever ask for. No its not some incredible love story good enough to brag about but the boy sure is.

  • Name: Em
  • Gender: Female
  • Age of Virginity Loss: 16
  • Current Age: 16
  • How would you categorize your story?: Loving
  • Country: USA
Oct 122015
 

My best friend is known as one of the biggest bad boys in our town. He loves to smoke his pot, get into fights, steal, & of course.. Be rude. Lets call him “C”.. “C” is rude to everyone except for me, the only time he can be a dick to me is if his friends are around. But once his friends leave he’s back to sweet boy “C”. Anyways.. One day me, “C” and one of his friends went out, we decided to head to the skate park down the street. “C” was of course being very rude to me by calling me names, talking bout other girls and comparing their looks to me. “C” and I use to like each other very much about a year ago our feelings for each other never went anywhere and mine for him eventually died down.

I got heart broken once he started comparing my looks with other girls and him trying to impress his friends by tearing me down, it hurt. I then began to cry and ran off. He felt terrible and chased after me, at that point I hated him so much I just kept running I didn’t care that he was chasing me yelling out my name to stop. He eventually caught up to me he grabbed me and wrapped his arms around my waste I kept crying with my hands over my eyes. He then said “babe I’m sorry, it was just a joke I never meant to hurt you.” I looked up at him and he had a tear running down his eye. “You’re beautiful” he said “can you please forgive me?” I nodded and gave him a big hug. I asked him if he wanted to go for a walk and he said yes. We walked on this path that lead into a forest, it was windy and I was getting really cold. We were deep in the forest all alone where he sees me shiver he asked if I was cold I said yes. He then took off his sweater and wrapped it around my shoulders then put his arm around me. He smiled then suddenly I leaned in and kissed him. He smiled again, grabbed my hips pulled them in close and kissed me again. This time it was much longer. I eventually told him that I was ready and wanted to have sex with him. Being the bad boy that he is and very experienced he always has his condoms on him. At first he said “no. I’m not letting you have sex with me. I want you to save it for someone special and I don’t want you to regret it after.” I told him that I was in love with him and that I wanna be with him more than anything. He kissed me and pulled my pants off, while I unbuckled his belt. He said “you don’t got to do this for me” I told him to do it. He said “I love you, always had & always will” & he went in. He went so soft & it wasn’t just sex we were both making love to one another. Gentle, passionate, love. A week after he asked me to be his girlfriend of course I said yes. We are still together till this day and we’ve been now dating for 3 years. I’ve known him since the 1st grade and he will forever be my best friend.

  • Name: Annie
  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 18
  • How would you categorize your story?: Loving
  • Country: USA
Aug 242015
 

I’ve been with this 16 year old guy for about 3 months. We made out and everything. He lives out of town, but people were saying he’s homeless and a gipsy. We live in a completely white country so all the brown people usually beg and are a gipsy. We did it at his house it hurt, but I really love him and he loves me. My best friend at the time said to tell her if it happened ,she thought he might have been using me for sex. After it happened I told her not to tell anyone, but she told her sister and her mum. Now we’re not friends anymore.

  • Name: lea
  • Gender: Female
  • Age of Virginity Loss: 14
  • Current Age: 14
  • How would you categorize your story?: Loving
  • Country: Croatia
Aug 232015
 

My boyfriend that Ive had for 2 months (I know seems short but we have alot of history) and I would meet up at night, I would go over to his and he would come over to mine secretly. Recently he came over and that was the first time we had sex. We were laying in my bed listening to music and we just started kissing, he was feeling me up and I could feel the boner he was getting in his pants. I was honestly so turned on. We’ve done other things this wasnt the first time we’ve met up at night, the last time he came over we were close to having sex but I wasnt ready so we didnt do it, but this time I knew I was ready.

He pulled my pants down exposing my G-string which he played with then pulled those off aswell, I took his shirt off and was scratching his back he started feeling my boobs so I took of the jersey I was wearing. He slid his fingers in pushing hard so I opened my legs more I laid down ontop of him and started kissing down his stomach I ended up giving him a blow job and as soon as I was done he slid it in. It honestly hurt really bad he kept asking if I was okay and said to wrap myself around him if it hurt to much, we had to be quiet because my dads room right next door so when ever the bed would start making a squeak he would slow down.

10-15 minutes later he came we laid next to each other kissing then went in for round 2 Honestly I have no regrets, it was unprotected but Im on the pill so Im fine with pregnancy and we were both virgins that night. We are currently still together.

  • Gender: Female
  • Age of Virginity Loss: 14
  • Current Age: 14
  • How would you categorize your story?: Loving
  • Country: New Zealand
Aug 092015
 

My boyfriend at the time was a German and he was my neighbor, we both got along at the time, we hung out and did things together; one day it was really hot outside like 100 degrees or so but we took a walk to a rental house bc his friend had just moved out of it. So the AC was still on and we kind of laid out on the master bedroom floor, me and him talked for a while but we made out too, I noticed that he was always touching my breasts in the process, so we sat down on the floor again and then got back up and kissed some more, we decided to just sit in the house nude, bc no one knew we were there, we had the house to ourselves and it just happened, I kissed him and he kissed me, he laid me on the floor gently and kissed me on the neck. The only thing he asked me if I wanted to try again bc we had already attempted to have sex before but he didn’t respond so great that day. But it finally happened, as he was inserting his dick he asked me if it hurt, I said no, he asked again and I said no just push it through. He said he didn’t want to bc it would hurt, I told him I didn’t care so he did and yes a tear came out of my eye but after that it just happened. I lost my V-card to my German boyfriend and I don’t have any regrets I just wish he wasn’t such a jerk after we broke up, but we had sex twice after we made up from our last break up, but it was still special. Oh yeah, this was a few months ago not recently.

  • Gender: Female
  • Age of Virginity Loss: 19
  • Current Age: 19
  • How would you categorize your story?: Loving
  • Country: USA
Aug 092015
 

Well, me and my boyfriend had been dating for a year & 11 months before we had sex. We had always planned it out & said we would get a hotel & we would smoke some weed and just chill when it happened. It ended up being nothing how I thought. I ended up sneaking and lying to my mom saying I was going to a friends house & I went to my boyfriends. That whole night we chilled and then it came to around 1am we were laying in bed playing music and he just started pulling my pants down and then my panties and he just slid it in, it wasn’t easy I was very tight and we must have tryed for 10 minutes trying to get it in. It hurt like hell but once it was in I enjoyed it so much. I didn’t bleed. And we did it on a mattress in the middle of his poppops apartment. Partynextdoor was playing and it made it a little romantic. I enjoyed the sex only disappointing thing was that I didn’t loose it somewhere more romantic. The day after we woke up had sex again it hurt but it was all fine after that. My house actually burned down that same day I lost my virginity. So I couldn’t really take in that I lost my virginity. Me & my boyfriend are still together going on 3 years and my first time was unprotected. I regret that.

  • Age of Virginity Loss: 17
  • Current Age: 18
  • How would you categorize your story?: Loving
  • Country: USA