True Story: Losing My Virginity....twice, In The Same Day!

[jdtum]

Losing my virginity twice in the same day.

 

Part1:

This is actually a true story but of course I’ve changed the locations. So a little about me and how I lost my virginity twice the summer before my 10^th grade of HS. I’m 5’9, about 160lbs, toned body…not muscled up, just wanted to keep everything tight – light brown hair that tends to go sandy blonde in the summer.  Well growing up in the deep South, sex was not a topic brought up in most families except for “don’t do it before you get married or you will go straight to hell!” comments or talking about the local tramp that got knocked up by the local drunk.  Us guys are always pushed to start dating certain girls from certain families. Well earlier on, I realized that I had to work extra hard to be interested in girls. I always thought I was just a “late bloomer” – hell, my older brother Ray was co-captain of the high school football team, one of the best baseball players and was always getting some early on.   He dated and messed around all through jr high & high school.  He was constantly having teammates over to swim in our pool, so I got to hang with most the guys. Ray and I were close. We were brothers but we were also best friends – very rarely did we ever fight or get mad at each other.  We’ve spent a lot of time together this summer, bc he will be a senior this next year and has received a baseball scholarship to the major university another state. As soon as he graduates, he will be moving there to get settled in, so we’ve been making the best of our time together.  They use to pick on me a little asking me if and when I had fucked my girl…and I always, just did the typical “shrug it off” moves and changed the subject.  I remember starting to notice the guys more as we got older.  I would look at their chests…some were hairy – some were smooth…some had tiny nipples, some were a little thicker.  I also would notice how differently their chest sizes were and how their abs were different. When I started looking at their abs I would notice how some had those v-lines that would disappear behind their swim trunks.  Something in me, starting to stir…I would try to put it out of my head  Every time I was with my girlfriend and we were making, I would start thinking of those v-lines and my 7in cut dick started getting hard of course my gf Abby always thought it was her.  I had to put these thoughts out of my head – I’m not gay…and being gay sure as hell wasn’t an option. My family and friends would kill me.

Well one weekend the parents were going out of town and left my brother Ray in charge…fat chance. Our parents told us we could only have certain people over but no more. No girls could be at the house past 7pm. With us having the biggest pool in our neighborhood, everyone came to our house. Anyway my brother could have his 2 bestfriends Luke and Mickey over to stay and I could have my bestfriend Will over stay. Saturday, several more friends came over that afternoon, including my gf Abby.  The guys were giving me hard time about not getting with her and still being a virgin. Well Mickey, who was a little more countrified. He had a big ol’ bumpkin head – sorta stocky, very hairy all over.  He was always pulling at his junk which was about 7 inches uncut and showing us his hairy ass. Anyway, he was standing next to me really giving me hard time asking if I just had a small dick  that was scared of pussy…he said “I hope you aint no fag – I’d hate kill one of lil’ brothers.  (Mickey and luke always considered me their kid brother also). My brother was like “dude, what’s the deal – when are you gunna hit it, I know your dick works and it’s not small. (we shared a bathroom and I thought I had shut the door and caught me as I was shooting my load into the garbage can.)  He, mickey and several of the other guys were laughing…so apparently he had told them he had caught me. Ray and I were close and he could tell I was starting to get upset but more embarrassed …and was like dude, it’s cool…we all jackoff – hell Mickey here does about 10 times a day….they all started busted out laughing…it was very evident that I was still upset and embarrassed. While all this was going on, I had noticed that Luke was getting out of the pool while telling the guys to leave me alone. As like Ray, I’ve known Luke my entire life. For years, I actually thought he was my brother since he and ray were always inseparable but never knew why he had to go to the house next door to sleep.  The 3 of us always hung out, played sports, games…etc. He was tall, blonde hair, bright green eyes, very pretty lips, no hair anywhere that I could see – he had one of those vlines on his very sculpted body.  I had seen his dick before in the showers and soft I looked like a monster. Luke, knowing me so well – he knew I was upset. He walked up behind me and wrapped his arms around me and was like guys…cut it out..he will get his when he is ready. He made a comment to one of the baseball players and making fun of him saying that I didn’t want to be like him and shoot my load all over the girl before I even got it in..and then he made a couple other comments that slipped my attention. Something was starting to happen. I could hear that Luke was talking and I could that the other guys were talking but it sounded like the teacher from Charlie brown. All I could focus on was these 2 strong arms wrapped around me… I was starting to get hot…that sun must be glaring on us…but it’s cloudy….I could feel the warmth of his breath on my ear and the side of my face as he is talking to the other guys….. I could feel rise and fall of his chest that touching my back – skin to skin. He was wet from being in the pool, it was cool –yet, felt great against my skin. But what really had me thrown off was that I was paying attention to how he felt up against my ass. I was starting to have all these crazy feelings…it’s not like I haven’t felt his groin up against my ass before, hell I’ve even sat in his lap before in the jeep headed to the lake…but this time it was different to me for some reason – although Luke’s swimtrunks were sorta thin and you could always see the outline of his dick swinging – I swear I felt it bounce a little against my ass a couple times…then I felt a rush of panic come over me – I felt my dick getting harder in my shorts…right there in front of brother and all his friends….what the hell is happening to me……

 

To be continued……..(Let me know what yall think)

[MackyJay]

nice start

[sleazebugga]

More please......

[bareall77]

Very nice start. Please continue. This could be a hot yet compelling story with likable characters. I personally prefer Luke!

[Docebrown]

Great start. Looking forward to reading more.

[Corkbb4poz]

Very nice

[Mvillebottom]

Great start, look forward to reading more

[jdtum]

WARNING: Some straight sex in this part. If you don't like that, skip this part of the story.

thanks for the encouragement. I know it's a little long...but I hope yall still like this.

________________________________________________________________________

Part 2:

I didn’t know what was happening to me. Here I was standing in front of my older brother and all his high school friends in and around the pool and my dick is starting to get hard. What the hell, why am I paying more attention to Luke, my brother’s bestfriend and a guy I considered a brother also. Ive seen him naked a million times, we’ve rough housed around my entire life, he lives right next door – so we always see each other… he is standing behind me with his arms wrapped around me like he has done before – our bodies were touching. His bare, wet, sculpted chest was touching my bare skinned back. I could feel the water running down my naked back and his naked chest all the way to tops of our swim trunks we were wearing as his crotch was pressed up against my high ass. Why am I paying so much attention to this, why am I all of a sudden getting these weird feelings…why did it feel like his dick just bounced a couple times into my butt cheeks. Whatever it was, set off something in me. I started to panic when I realized that my dick was getting hard in my shorts and then came back to life as Mickey yelled.. “hey luke, you pinch’n Ryan’s little tits…he’s starting to get some wood” I was in panic mode as started to cover myself and try to figure out what to say..wait, did Luke’s dick just up against my ass again? I felt Luke’s grip around my body tighten and told the guys…”turn around and yall will see why Ryan is getting hard”…that’s when I focused on the end of the pool and saw that Ray’s girl of the month was rubbing tanning lotion on Abby, my girlfriend. Then the guys, led by Mickey was like ahhhhh yeah, lil’ bro gunna get him some tonight! Oh yeah. You know, typical hs locker talk…ray was like “why don’t you and Abby go up to the game room and hang out….in the bottom drawer of the green cabinets toward the back are some condoms…make sure you use them.” Then Ray shouted to Abby saying that I wanted to show her our new pool table…” of course Abby was game..she knew where this might lead – she had told me she was ready since she was a year older than me. All of sudden I felt cold and realized that Luke had stopped holding me but I could still feel our bodies slightly touching as he stood behind me. As Abby walked around the pool and all they guys with shit-eat’n grins on their faces, my dick had gone back to normal…thank goodness….As Abby got to me…she grabbed my hand and said lets go…as I turned around I looked up and met Luke’s gaze into my eyes like a million times before, but there was something different this time as he smiled at me. As I moved passed him, I felt a graze against my dick but this time it felt like it was almost on purpose – but it couldn’t be. Luke was straight, had a girlfriend and me and ray had walked in on them having sex before…no, he’s not gay. But I turned my head back to him and noticed he did another grin and winked at me….

So me and Abby get up to the game room and we start messing around and while we were kissing she was massaging my dick….”did Luke really touch my dick on purpose?” “what was with that smile and wink?” “he looks really good…..” my attention was broken again as Abby snapped me back into focus…along the major discomfort I was feeling….”You must really like that & me…you are super hard” – I realized that my dick was hard and confined in my shorts…What was going on with me….I’m sitting here kissing my girlfriend while she is rubbing my crotch and all I’m thinking about is Luke and how he felt so strong as he was holding me and the wetness from the pool running between….focus ryan abby said. I am ready to do this with you and by the looks of it, so are you, abby said. My sister told me that since we are both still virgins, that I should give you a blowjob first bc you would probably last longer on your second ejaculation. I was nervous but said okay….we both got undressed and laid on the floor kissing. She started licking the sides and stroking it…of course it was hard, I’m a teen. Wind blows against it, I’m hard….but all I could think was I was about to lose my virginity with my gf while my brother and all his friends were downstairs…with Luke….damn, my dick jumped and I realized that Abby had swallowed my dick and thinking of Luke my dick thicken causing her to gag a little. As I focused on her it just wasn’t as hard as it been earlier. She noticed and asked if she was doing something wrong. I told her it felt great, I was just a little uncomfortable on the floor like this…so we moved to the big chair in the corner. Here I was able to sit and lay back and let my full balls hang over the side of the leather chair. As she scooped up my balls and started licking and sucking on them and swallowing my dick, I leaned back and closed my eyes and tried to focus on the sensation but all I could focus on was Luke. I was picturing his tall, sculpted body….how the water dripped from his blonde hair down the side of his chiseled face to his thick neck…what is going on, I thought…am I gay…I can’t be – it’s not right…those shorts really are fitted on him…it really showed his dick swinging today. Omg – what is going on…I’m straight – ive got a girlfriend, I’ve got to get married and have kids….my family will kill me. But I just really am having all these crazy thoughts about Luke. Luke with those beautiful green eyes, those full lips…I just love how his nipples are tiny…but they are hard, I could feel them in my back as he was holding…..oh his arms felt warm and strong…..it was cool how for a moment it felt like our breathing had matched up as his naked torso was pressed up to my naked back….his torso…so tight and tan…that six pack that is really starting show…that scar on his right side from when Ray flipped them on the bike years ago….but that scar is right above where his v-line starts going down to his shorts that were pressed up against my ass…was that his dick that bounced…oh I can just imagine what it looks like hard…thick and veiny just sticking a mile out in front of him….ohhh damn, I’m must be getting cold I’m start to get chills and shake…but I wonder if his skin rolls back over the head so it looks like he is cut like me or if it just hangs….i wonder what it would be like to hold something that big or even taste it….OMG I can’t breathe oh this pressure….what is going on. I refocus and realized that I’m shooting cum all over the place. Abby was trying her best to swallow, but that was a lot of cum. I can’t believe that I thought about Luke the entire time she was sucking me. I was so wrapped up in thinking about him that I didn’t focus on Abby giving me my first blowjob.

As I’m sitting there trying to catch my breath, My mind is going 90 to nothing…what is wrong with me. Maybe I’m just so horny that I’m thinking about everybody. I can’t be gay…I’m just horny like Ray and Mickey said. Refocus….Abby is cleaning up a little, I walk over to the bar counter to get us a couple paper towels…I give some to abby then I go back and I tear one off and wipe the cum off my stomach, dick and balls…then tear off another to wipe the sweat off my face…that’s when I look out of the window and see Luke laying there probably asleep on the chair in his shorts and sunglasses with the water glistening on his body now that the sun had come out….God his body is beautiful..i felt my dick bounce….what is going on with me…this can’t be happening…I lean down to the counter to gain some composure then I glanced back out the window and down at Luke….his hand was rubbing across his chest slowly….my dick bounced again…he then started to move his hand slowly back and forth down his rippled stomach…omg my dick was starting to rise….what is going on….wait, is he going further….he rubbed all the way down to the top of his shorts and just pulled the band down a little as he worked his hand down the side of his shorts…….i’m thinking, he has to be sleeping – he can’t be awake and doing that…I then noticed that my dick is bouncing against the cabinet door….lukes hand was moving so slowly up the side of his shorts…then he adjusted his dick….my dick went solid I and I had to step back. Holy shit…my dick got hard by watching my neighbor, my brother’s best friend, my brother readjust himself….

To be continued….. (let me know what yall think)

Edited August 30, 2016 by Herts
Added warning

[jdtum]

WARNING: Some straight sex in this part. If you don't like that, skip this part of the story.

Part 3:

Holy shit…my dick got hard by watching my neighbor, my brother’s best friend, my brother readjust himself….what is happing to me….I can’t be gay! Abby walked over and asked me what I said bc she couldn’t hear….(oh hell, I’m starting to say it out loud) Oh nothing, babe….she then noticed that I was hard…and asked I was ready for their next step. I glanced back down at Luke….his hands were back behind his head again not moving……(did he move or did I just imagine that – refocus) . Abby had started kissing me again while stroking my dick….then I noticed she had was rolling a condom on my dick. I guess, Ray’s girlfriend knew where they were….she pulled me over to the couch and laid down. I looked at her as she was naked. She is so beautiful…her pubes, nicely trimmed…were darker than mine…(I wonder if Luke’s is blonde or if he has any)(FUCK – what the hell I’m not gay – stop thinking about him) (I’m about to fuck her and prove I’m straight…) I lean in kissing her and she grabs my dick and starts putting it inside her. …I exhale as she gasps….remember, we are both virgins and I have a hard 7 inch moderately thick dick….I was scared I was hurting her, but I was more scared of being gay…..I was trying to wiggle it in as slowly as possible. I do really care for Abby & I didn’t want to hurt her….after applying more lube and taking a little extra time…I had done it! I have officially lost my virginity! ( I am a man, I am straight, I am not gay…I was just horny) while I’m sliding into her slowly, in my head I’m just repeating in my head that I’m straight, this is right…this is the way it’s supposed to be) - it was then that I and abby released that I was losing my hard on. I was starting to panic….i don’t think I came again…Abby could see the panic on my face. So she suggested that we change positions. And let her ride me. By the time I had pulled out and gotten repositioned I had gone soft. I was scared. What happened? Again, she saw the look of confusion and disappointment and don’t worry….babe, don’t worry – this happens…I told her, I’ve never gone this soft after being so hard and not Cumming, She asked if I had ever had a condom on for a time period? I thought about it and said…actually no… I thought about the first time I ever dealt with one. I had been in Ray’s room doing something and came across one. So I opened and was looking at it and playing with it. Of course being a little younger, the idea of sex got me hard….so I decided I would try to put one on…you know, just in case I got lucky sometime. Well striped down and was sitting on the end of the bed when Ray walked and I freaked. He started laughing and told me not to cum on his stuff. He then saw the open condom and he asked me if I had put it on yet? I said no, I was about to try. He was telling me about how to pinch the tip to get a little extra room but he saw that I was confused…so he said here…let me show you and wen to put it on my dick. Of course I was like hell no…so he said he would show me on his own dick. He popped in a dvd then all of sudden porn came on – my dicked jumped. Well he stripped, I blushed and he said – look, we are brothers – we both have one – no big deal….so I watched as he got hard….it put mine to shame. He sat there stroking his at least 9in cut dick with his huge hairless balls underneath. He got another rubber and put one on. The entire time this was happening, I was hard & didn’t really pay attention until he pointed it out. So gave a fresh rubber and I started putting it on…well I was having a little trouble – so he was like let me show you again…so he pulled my arm and the rubber and placed it at the tip of my dick and then said, you will then just wrap your other and around and roll it to your pubes and he demonstrated across my head…after that, I finished rolling it on. “you good? You got it?” yup I do! - well you’re still hard and might as well not completely waste these rubbers…here.. He put a little lube in his hand and grabbed my dick and did a couple strokes…that was the strangest feeling I’ve ever had. Well it didn’t take long for me to blow my wad into the condom….Ray was still stroking his when he asked me to wrap my hand around his balls and give a slight tug. So I did and it wasn’t long till he filled up the end of his rubber with the most cum I’ve ever seen. I grabbed my clothes and was headed to my room and he said, anytime you want to jackoff together, just come on over. I’ve got a good stash of porn.

Anyway, When abby asked if I had used a rubbers before….I said no, but told her I had put one on years ago, but not sense then. She said I probably wasn’t use to them that she heard her brother say that his dick wouldn’t stay hard with them so he and his girlfriend never used them. I knew Ray hardly ever used them…I think he has had the same stash for years. So Abby suggested that I try entering her without one but just make sure I pulled out if I felt like I was going to get close. So I walked back over to the counter and got a little lube and started to put some on my dick…there was a response. I then looked out the window, and there he was…still laying there. Abby told me that taking it off worked…I was refocused and realized my dick was rock hard! Abby grabbed my hand to pull me back to the couch…I glanced back and saw Luke’s head move up as if he was staring up at us…maybe he was just shifting his head on the pillow or something. But I asked Abby if we could try something, might be a little fun. I told her let me sit in front of this window in this chair and you could get on top then lower yourself at your speed. Abby looked down at everybody to see if anyone could see…nobody was looking at the house. Pretty mush all the guys were in the pool with a couple girls. Then a couple were in chairs, but figured they were asleep. She was nervous but she decided to try it. I sat down with a clear eye shot to the pool below and then Abby starting working her way down my hard dick. Oh the sensations were great. I really am a man, I’m sitting here fucking this girl with no rubber on. Just skin to skin – pure. Although we had connected, I just wasn’t satisfied. I started looking around and then saw Luke’s hand move to his glasses to lower them a little. I wasn’t sure if he was looking at us or someone else. I saw him get up and move out of my vision. Where had he gone? I could tell that Abby was done with this position which was good bc I did want to last longer but felt my balls start to tighten up. So I was like hang on…lets try something else. I told her I had seen this position in one of rays movies and said that the girl really liked it. When I stood up I saw that Luke had moved further back and away from everyone else, again he was now laying more upright but noticed he had a towel over his legs…Abby broke my thought and ask how I wanted to do the next move. I told her to stand over the back of the chair which was behind the bar, she did. I walked up behind her and she freaked thinking I was going to fuck her in the ass….I was like hell no…that is gay shit. I was gunna stick my dick in her puss from behind. So she repositioned herself over the chair and helped guide my uncovered raw dick back into her. She reminded me to pull out. So here I am starting to stroke in her and I look at her smooth back going down to her ass…it was very beautiful – couldn’t really tell it was a female until she made a sound. I glanced down for a moment it looked like Luke was doing something under the towel. Maybe he was just readjusting himself, but it seemed more than that. I all of sudden wondered – what if he was staring at me and was jacking off….that did it…that one thought made my ball shrink up and shot my load….then I panicked bc I realized that I was still in Abby – we both freaked. She started screaming at me telling me I should have pulled out – I tried to tell her it was an accident and that it just happened so fast. I told her – wait here, I’m gunna go get ray – he will know what to do. I threw my shorts on and ran downstairs yelling for Ray….I told him COME HERE NOW…he jumped up and was like what the fuck - what happened…I told him & he started laughing and then I punched him and told this is not funny, I can’t get a girl pregnant yet…mom would kill me…I started sobbing….Ray took me and held me for a second…Ry, it will be okay – this has happened to many times and he would take care of this. So he went and got his girl, apparently he told her bc when they came back, she oh hun, it’s fine – this happened to me last week with Mickey. Ray shot up, Mickey, really? Damn. Anyway, the three of us went upstairs and ray’s girl told abby what to do. I was still crying and Ray told me they were gunna go get the morning after pill for her and then take her back to his girls house – then he punched my arm and said, he was gunna go get some after they got finished with abby. Well Abby collected her things, she didn’t speak to me as we all walked down the stairs…I told ray I was so sorry..he grabbed me and gave me a tight hug, then gave me kiss a little off to the side of my mouth and told me he would take care of it…try and relax – Mickey and Luke will be here…just don’t let Mickey fuck the dog when he was drunk….they all left. Ray must have told mickey bc he came up to me and was little bro, it’s all good…..happens to me all the time. I tell them ho’s opps the rubber broke or opps I forgot to pull out….it’s all good lil bro. I put on a brave face in front of everyone.

They all decided to go up to the game room for the rest of the afternoon as they waited for pizza that was ordered. I walked out and sat on the side of the pool. I was still panicking in my head. I can’t be a dad yet…I’m not out of school yet…plus I’m confused with other things. Then all of a sudden I felt a hand on my shoulder. I looked up and it was Luke. I sorta freaked – here I am stressing about knocking up my girlfriend and the fact that I’m having bad thoughts about…with him. I started crying again. Luke sat down beside me and told me that Ray had called him and told him that everything would be fine – but he was going to stay the night over at his girls house. For him, to keep an eye on me and make sure that everyone was out of the house soon…..and also to make sure that Mickey didn’t fuck the dog. Luke gladly excepted saying he would take good care of me….

To be continued……Sorry it’s so long, but I’m trying to get the struggle that some of go through on these journeys

[MackyJay]

Not too long, but damn hot for sure.

[Hellboy]

Hot start...

[Guest]

I'm looking forward to Ryan losing his virginity to a man, Luke, then to his brother and all of his friends

[barekinkfun]

Hopefully a new chapter is coming so that we find out how Ryan lost his other virginity, whether Luke and Ryan got it on, did Mickey get drunk and fuck the dog? let us know soon please.

[Spike1108]

is there a part 4?

[punaman]

yeah, want to see him get with Luke, enough of Abby