Where it happened: Parent's basement
Langauge: english
Sex: Female
Rating: 10
Category: Straight
This was not actually my first sexual experience, but was my first sexual experience with a guy, actually two guys. My first experience was with another girl, Suzie. We dated for 11 months and ended up having sex a couple times a week. She very quick introduced me to her dildo then shortly after she bought a strap-on. We were really into each other but we both really loved vaginal penetration. I absolutely love giving and receiving oral sex with other women, but my absolute favourite sex acts were (and still are) vaginal and anal penetration. Therefore, let me tell you about my first sexual connection with a guy (s).
I started my relationship with Suzie when I was 14. We broke up 11 months later in August 2001 as she was leaving to go to school in another province. Sadly a month later she passed away of a drug overdose just 2 weeks after 9/11. January of 2002, my mother and father came to me and told me that the auto parts plant my dad was the manager of was closing, and that he was being transferred to the company’s head office in Michigan. My mom had a successful accounting practise in my hometown and besides they didn’t really want to take me out of my high school. Therefore my dad worked in Michigan during the week and came back most weekends. My mom kept our house and my brother and I stayed with her. During this time, there was so much upheaval in my life with the still painful loss of Suzie, dad being gone several days a week and the general angst a teenage girl can go through. I was really missing sex but given all the stuff I was dealing with, it was just easier to pleasure myself.
Things would change in July 2002. I didn’t have a regular summer job as I worked at the local Cineplex. Some of my shifts were afternoons, but most were actually evening shifts and therefore I was often home during the day. A couple of my guy friends also worked there, and we’d hang out whenever our shifts lined up, go for hikes or go swimming, typical summer stuff. One day in early July we were swimming down at the beach. I usually wore a two piece bathing suit as I felt I had a reasonably good body. I played basketball and soccer in high school and was in good shape. Derrick was my age at 16 and was also quite athletic, playing a lot of rep hockey. He was a very confident (maybe a bit cocky) person, sometimes annoyingly so. Ben was a year younger and while he was also in great shape and a hockey player, he was quite quiet and shy. I actually preferred spending time with him as he was just a great listener and always made me feel special. Still, I just wasn’t looking at either guy for sex or relationships as I was still thinking I preferred girls. I found myself looking at girls much more than guys based on my experience with Suzie. Still, when I was down at the beach that day, my mind opened up a little.
The water was still rather cold that early in July despite a recent heat wave. We got to the beach and I peeled off my tshirt and cutoffs – the boys also pulled off their Ts and in we went. The water was cold but we quickly got used to it and stayed in for probably 15 minutes or so. While doing so, the wind came up and some clouds started to roll in. Ben had heard it might storm that afternoon, but when we sat out for the beach there wasn’t a cloud in the sky. We got out and sat on our towels for a few minutes. Despite the heat, the wind had really cooled things down. We were talking about all sorts of different things, sports, the next big party, the latest gossip, that sort of stuff. I noticed Ben getting a bit uncomfortable while Derrick just had a big stupid grin on his face. I began to notice he was looking at my chest, in fact was having a hard time taking his eyes off of it. I looked down and noticed my nipples were very hard and erect under my bikini top. I guess the wind had a put enough of a chill in me to make them come to attention! Ben then started to turn his back to me. I didn’t understand this at first. Meanwhile Derrick just sat there grinning and staring at my breasts, not caring to be discreet. I just stared back at him and reached for my T-shirt and shorts. As I was pulling them on, my eyes flashed across his midsection. He had a very obvious erection! I’m sure I must have turned very red as my cheeks literally started to burn. Fortunately the awkward situation was abated when the now overhead clouds started to open up. The clouds were growing darker by the minute so we knew this wasn’t going to be a quick shower. Derrick said that we should go back to his house and watch TV. Given that his house was only a 5 minute walk from the beach, it seemed like the best plan. As we got within two blocks of his place, the clouds really opened up. We sprinted back the last couple hundred metres and under his covered porch. All three of us were drenched so Derrick said we should go down to his basement where we could watch TV and chill out.
Both of Derrick’s parents worked day jobs and weren’t home. His older brother was home from university for the summer but worked as a bartender at a local resort. After a half hour of channel surfing and not finding anything interesting to watch, Derrick suggested we watch a movie. Ben asked what he had and Derrick just laughed. Said he was going to grab his brother’s video collection and I noticed that Ben immediately blushed. Wasn’t sure what that was about but I soon found out. Derrick came back with a small box of CDs and asked what we wanted to watch. He started reading off a bunch of cheesy titles that I almost immediately figured were porn videos. I was instantly disgusted as any proper girl should, but quickly I began to think that I actually wanted to watch some of this. I just didn’t want Ben and Derrick to think so right away so I protested mildly for a couple minutes more. Finally I said something like “Ok, fine”, and Derrick couldn’t move fast enough pulling a CD out of the box. The first CD wouldn’t play for some reason so he yelled at Ben to pull another one out of the box. The second CD played. At first I was a bit disappointed – the video quality wasn’t very good at first and it appeared to be made back in the 80s sometime. Ben said that it should be a good video though because it starred a guy names John Holmes. This surprised me a bit that he would know this as he always was so quiet and not the type to watch this type of stuff on a regular basis. Later in life when I started to work in the adult film industry I learned just a legend he was!
As we watched the video, Derrick was sprawled on a big easy chair constantly looking over at me and not hiding the fact that he had a raging boner. Ben curled up in a ball facing away from me – I still wasn’t quite sure what was up with him. About a half hour into the video Derrick got up, said he was going to the bathroom. He leered at me as he walked by me and wasn’t trying at all to hide his erection. He was gone over 10 minutes, later in life I finally understood what he was likely doing! Meanwhile I was starting to get into the video and was getting serious turned on. The penis on John Holmes was absolutely massive and I actually shuddered thinking about that thing inside me. It appeared to be much larger than the dildo or the strap-on that I had used before and I thought it would split me in two! Still despite the thoughts of pain, I began to wonder what it would be like to have a real penis in me. My pussy was getting very wet and my nipples had returned to their stiffened state. I was really getting into this and was legitimately confused that I could actually be wanting a guy inside me. I was also quite confused about having a guy’s penis in my mouth, not before today had I ever imagined wanting that. The moment I saw one of the guys cum into one of the actress’s mouth I was instantly disgusted and yet moments later I was so aroused!!
About 5 minutes after Derrick returned from his extended “bathroom” break, we saw Derrick’s dad’s car pull into the driveway. Derrick frantically pulled the DVD out of the player and stuck it back in the box before sprinting back to his brother’s bedroom. Moments after returning to the TV room, Derrick’s dad called out to him and he went upstairs. A minute or two later Derrick came back down and asked if we would mind going home. His dad had left the office early not feeling well and he just wanted to rest quietly. While I was disappointed in not seeing the entire film, I almost felt it was a blessing in a way – I wasn’t sure how much longer I could have lasted before having to take my own extended “bathroom” break!! As I was getting up to leave, Ben did as well. I only caught a glimpse of it, but his crotch had a big wet stain on it and the bulge made Derrick’s look small! I was shocked yet strangely excited.
Interestingly I was scheduled not to work that evening at the theatre and had previously made a date with a few girlfriends to get together as they all worked daytime type summer jobs and it was hard for I to get together with them on a regular basis. I didn’t say anything at first about my unusual experience that afternoon with Ben and Derrick. I knew that our conversations always rolled around to sex anyway at some point so there was no need. All three of my girlfriends were sexually active in some manner, but given that I didn’t want to divulge my lesbian relationship with anybody, I played the role of the innocent virgin with them. Sure enough my one friend Kate started complaining that her boyfriend Dave was continuing to pressure her to suck his dick. She had had a bad experience with a previous boyfriend who had cum in her mouth without warning her and it turned her off to the entire experience. However, my other two friends were big fans of performing oral sex on guys. Amanda had the reputation of being the school slut but truth be told, at this point in 2002 she had yet to actually have sex yet. However, by her own admission she had given head to over 30 guys by this point (remember, we were all 16 at this point) and was the queen of every party to say the least. Guys would practically line up to try to get her drunk enough to get her to service them. She professed that she really enjoyed the experience (she said most guys tasted really good, something I was eventually to learn was not always the case) and that it allowed her to feel sexy without having to give up her virginity until at least university (made sense to me then but I realize now she must have had a screw loose). Julia had been dating the same guy for the past two years and they had been having sex on a fairly regular basis for the past year. We talked some more and I left them feeling like I wanted to have some type of sexual encounter with Ben and Derrick, but serious didn’t think it would happen the next day!
The next day, Ben called me in the morning. He had spoken to Derrick and apparently his dad was still sick. So we made plans to go to the pool instead of the beach that day instead as it was much closer to my place where we could go to make a late lunch. We were at the pool by about 11 AM and the sun was already high in the sky and the temps were rising quickly. I was in another 2 piece bathing suit despite thinking that morning about going with a less revealing 1 piece. I’m still not sure why I made the choice I did, maybe I was looking for something to happen that day after all. In the pool we went and while it was quickly becoming a scorcher, the pool wasn’t very busy. Most of the others there were young parents with babies or toddlers and stuck to the shallow end of the pool. It was basically just the three of us and we spent our time goofing around, splashing each other. At some point, Derrick came up behind me and put his hands briefly on my hips and spun me around. I splashed him playfully and he let me go, but not before letting his fingertips run down the sides of my thighs briefly. I felt a chill run down my spine and I instantly got a little horny. I turned and looked for Ben – he was treading water a few feet away so I swam over to him and gave him a playful shove. He grinned and went to shove me back. However, I saw what he was trying to do and as I pulled upwards and back his hand, which moments before had been on target to playfully punch my shoulder ended up catching me square in my left breast. “Did you get a good feel” I blurted out laughing and he turned beet red in embarrassment. I instantly felt bad and swam back to him to give him a friendly hug. When I wrapped my arms around him I felt a poke from something in my upper thigh. I didn’t say anything but moments later I realized it must have been his erection. By now I was becoming increasingly horny and I felt like I needed to remove myself from this situation. I rather lazily swam over to the ladder and said to the boys that I was just going to sit by the poolside and work on my tan for a few minutes. Truth was that I felt like I was starting to lose control of myself and I just had to get away from them for a little while. Derrick started squawking that he was hungry and that we should back to my place for lunch but Ben wanted to wait a bit – I think he still had that raging boner!!
After another ten or fifteen minutes Ben finally got out of the pool, we toweled off and set off for my place. Mom had known that the boys were coming over for lunch and had gone shopping quickly at lunch to pick up some sandwich meat, rolls, carrots and some cookies. She left a note on the counter as to where everything was and we set down to start making sandwiches. Now you might find it odd that my mom would knowingly allow two boys to come spend the afternoon, but she was pretty cool for a mom. I appreciate her even more now than I did then. The previous summer in 2001 I went on birth control pills to help deal with menstrual issues like cramping. She took me out for ice cream the evening after the doctor’s appointment and we went down to a local park to sit and chat. She said that she too had suffered severely with menstrual cramping when she was younger and she was hoping the pills would help with that. She just asked that I not use being on the pill as a licence to start having sex (again, she didn’t know about the extent of my relationship with Suzie) but rather wait for a time when I was mentally ready for sex. She said that she hadn’t waited until she was married (this freaked me out a bit inside – I don’t think anybody likes to think of their parents doing it ;-)) and she didn’t expect me too, but she just asked that I at least be comfortable with my decision.
So as I was making my sandwich, this all came flooding back to me and I began to wonder yet again if I really wanted to do something sexual with these guys. They were both very good looking guys, and Ben in particular seemed to care about me. I just didn’t know. Part of me just wanted to try something, while another part of me was completely questioning who I was. A couple of days ago I was sure that my future only involved other women, and now the thought of having a go with a guy was making me wetter than ever. Anyway, I thought we would just go downstairs and watch some TV or play some music after lunch and I just parked these temporary feelings of anxiety. After all, I didn’t have any porn…..
Within twenty minutes, we had finished our lunches and were just sipping on our Cokes. We went downstairs and turned on the TV. We have one large sofa situated in front of the TV and a couple lazyboy type chairs either side of the sofa. The problem with the lazyboys is that because of the shape of the room if you sit in either of the chairs, you don’t get a good angle at the TV. Anyway, I was last downstairs as I loaded the dishes in the dishwasher and put away the rest of the meat and condiments. When I got down there, I saw that Derrick and Ben were sitting either side of the sofa, leaving room for me in the middle. I didn’t think much of this at the time but it was to play a role maybe a hour later. Like yesterday, nothing much was on and in about a half hour, I got up to turn off the TV and throw a CD in the stereo. Derrick suddenly spoke up and said he had something we might want to see. He reached around the end of the sofa and pulled up his backpack, which he must have brought downstairs with him. He reached in and pulled out several DVDs which I suddenly realized must have been more of his brother’s porn collection. While before I might have recoiled at the prospect of watching porn, today I surprised myself by saying “awesome”! Derrick picked one at random and inserted it in the DVD player then came back to sit beside me on the sofa. I did notice that he seemed to be sitting a little closer to me this time and wondered if that meant anything. I can’t remember the name of this particular video but it was much more recent than the John Holmes one we watched the day before.
The actors or “performers” didn’t waste much time in getting into the action and quickly the warmth between my legs returned. It was at this point that I realized I should have put a tshirt on as my nipples were getting hard. I also noticed that Derrick had slid even closer to me and was sporting an obvious erection. I glanced over to Ben and even he had slid closer to me. I was suddenly finding it hard to catch my breath and wasn’t sure what to do next. Part of me was hoping one or both of them would jump me while another part of me was saying to myself that this wasn’t right. Yet another part of me was wondering if I should make the first move. All this time and I was still overthinking things. What to do?? Then Derrick made my decision for me when he placed his hand on my left knee. My breath audibly caught and he slowly began to rub his fingers up and down on the lower part of my inner thigh. I was in heaven yet still nervous. Then I felt a hand on the top of my right thigh and I looked over to Ben working his fingers up to the top of my thigh. OMG, I couldn’t breathe! I didn’t spread my legs so much as simply rolled my knees to the outside to give the boys a little better access to me. They continued to run their fingers up toward my soaking wet pussy. As they got closer my hips began to involuntarily wiggle, and moans were escaping my lips in between ragged and irregular gasps of breath. I so badly wanted their fingers and their tongues inside of me yet I was still experiencing some conflict. Yet as Ben moved his finger from the inside of my thigh to the outside of my bikini bottom I could feel the stirrings of my first orgasm building within me. As he ran his fingers down between my pussy lips (my bottom was still on) I came almost instantly, my hips shooting towards the ceiling with only my shoulders and feet still touching anything. Wave after wave of intense pleasure hit me like never before. I lay back and all I could say is “oh wow, oh wow”. However, the boys weren’t done. Ben looked like he had already cum in his bathing suit but he was starting to gently lick and kiss my tummy. Derrick meanwhile had moved down onto the basement floor and was spreading my knees apart. He began to kiss the insides of my thighs and was working his way up. Ben had worked his way up to my breasts and had moved his hands up to my left breast, gently squeezing it as he stared curiously at it. At this point I raised my right hand to his chin and guided his lips to mine. I could tell Ben was a little nervous but we smooched and I gently stuck my tongue between his lips until we touched. I started to wrestle with his tongue a bit and by this point he was getting the idea. I wrapped my arms around his neck and pulled him passionately into me.
Meanwhile, what Derrick was doing between my legs was absolutely incredible. He was slowly licking the insides of both my thighs and was nearly at my pussy. Then I felt his tongue begin to lick my lips through the bikini bottom. Bang! I had a little orgasm right there and actually nipped poor Ben’s tongue due to the surprise. Ben pulled back and looked at me with a puzzled look – all I could do was look sheepishly back to him and shrug “sorry!” He obviously forgave me as he came back in to kiss me. Then I felt Derrick’s hands reach up to my hips to try and pull my bikini bottom off so I lifted my hips up to allow him to slide them off. He attacked my pussy with a vengeance and even though it became apparently pretty quickly that this was his first time doing this, he hit all the sensitive bits enough for me to start to feel my third orgasm begin to well within me. I’m still making out with Ben at this time and I let my hand wander down to his penis which I grabbed softly through his bathing suit. He was already hard as a rock but I could feel him stiffen even more as I held him. He groaned loudly and said “careful or you’ll make me cum” to which I said something like “isn’t that the point” and grinned. By now Derrick was hitting my clit with regularity and I was getting closer to my third orgasm. At this point I guess he decided it was a good idea to stick a finger inside me. This pushed me right over the edge and my last but most intense orgasm of the day sent me squirrely – my hips were bucking and I was swearing to God and a lot of four letter words (which I don’t normally use much of) spewed from my mouth. Waves of pleasure kept hitting me for what seemed like minutes but were likely only seconds and finally I collapsed back against the sofa. I was still holding Ben’s penis through his bathing suit but I suddenly I realized my hand and his shorts were all covered in his goo. I looked up at his face and his eyes were nearly rolled back in his head! I guess I didn’t let go of him when Derrick got me over the top and I basically jerked him off as I was shuddering through my orgasm.
I closed my eyes for a few seconds and I’m sure I had a really big smile on my face. I opened them when I felt my legs being spread again and saw Derrick with his penis in his hand moving in to enter me. I grabbed his penis and yelled “whoa” or something to that effect. I don’t know if it was some sort of sudden regret on my part or I was trying to salvage some sliver of my previous good girl image, but I told both boys that I wasn’t just going to give up my virginity (they didn’t need to know that I had already given this up to Suzie) right away, but that they’d have to prove they could be quiet and keep this all a secret if we were going to start this special privilege amongst us. “We are going to stick with oral sex for now. We won’t be doing “it” for a few weeks at least – I’m only going to do that when I feel ready and I feel I can trust the two of you”. The look of disappointment on both their faces was almost funny but I think I got my point across. Derrick almost seemed to sulk and basically said that was easy for me to say because I was the one who was having all the fun up until now. “Don’t worry, we’ve a great opportunity for all three of us to learn a lot more about sex this summer – we’re all going to have a lot of fun” I said, and tried to put on my sexy face, looked back and forth between both of them and said “both of you are going to leave this afternoon with big smiles on your faces”. I smiled devilishly at both of them and felt something funny in my left hand – I still had ahold of Derrick’s penis and he was getting hard again!! So I reached down with my right hand to Ben’s swimsuit, put my hand inside and pulled him out. He was hard again already.
I looked at both of them and said that I just realized I had a problem. “Which one of you do I suck first?” That produced groans from both of them and I thought Ben was going to cum again right there. By now, I was really getting into the bad girl thing and I just shook my head. I said something that to this day I still shake my head about – “I’ve always wanted to know what a guy’s cum tastes like” and I licked my lips. Ben looked like he was going to faint and Derrick had finally stopped with that wolfish grin of his and just sat there staring at me slack-jawed. Had to admit I loved having a bit of power over these boys. But how was I going to choose which one to blow first? Then I remembered there was some change on the end table so I asked Derrick to grab me a quarter. I told Derrick he would be heads (never even got that pun until now!) and Ben was tails. I flipped it up in the air, caught it with my left hand and slapped down on the back of my right hand, covering it so neither could see the result. Then I waited to tease this out a little longer. A series of groans from both of them told me this was having the desired result! Finally I pulled my hand away to show that heads was the winner and it was Derrick’s turn to nearly faint. Ben looked devastated so I looked at him and said “tough luck on the flip, but to be fair guess who’s going to fuck me first”, gave him a wink and a quick tug on his little guy. It took him a moment to get it, but then a big smile leapt across his face and he nodded. I released him while still holding on to Derrick and pulled him up to his feet, turned him around and sat him down on the sofa. Now it was my turn to get down between his knees and as I approached his stiff penis I could almost hear him struggle for breath. A couple inches from his head, I stopped and gently blew on the head and up and down his shaft a bit. He started moaning as I scrambled to figure out my next move. I had never sucked a penis before and hadn’t even practised on my dildo. My total breadth of knowledge stemmed from the 2 pornos I had watched in the past 24 hours. So I started by licking around his head for a bit and his moaning continued. I began to intermix my licking and gentle sucking of his head with longer licks and kisses up and down his shaft. Meanwhile, Ben had moved in close to me and was just gently stroking my lower back and running has hand over my butt. It felt really nice and soothing, but I was much more focused on the job in front of me. After a couple minutes I somehow got the sense that Derrick might cum soon so I put mouth around his shaft and started to move up and down while continuing to swirl my tongue around the bottom of his shaft. I stopped for a moment and asked him if he wanted me to slow down, if that would keep him from cumming for a few more minutes. He just shook his head and I started again, moving slowly at first but every few seconds stepping up the pace. By this point I was quickly figuring out that if I also stroked his shaft with my fist it took a bit of the strain of my jaw. Also by this point, Ben had moved his hand down and was gently stroking between my butthole and my vagina. Even though I was trying to stay focused on Derrick, I was hoping Ben would put his fingers in me, really hoping he would….
Now Derrick was starting to quiver and shake and his hips were begin to buck a little too so I knew I would be getting a mouthful at any moment. I squeezed my lips just below his head while stroking his shaft faster and faster. All of a sudden, he thrust his hips up a bit and he groaned louder than before. I could feel his cum explode against the back of my throat and despite an urge to gag I just started swallowing. He kept shooting and I was struggling to keep up, but finally he stopped. I marvelled at the taste of the last few drops – very salty yet tasty. I was always into salty things more than sweet treats – good thing I guess!
I rolled off of Derrick and we both sat on the sofa. Ben meanwhile came and sat down beside me on the other side and just looked me in the eyes. He just smiled and squeezed my hand for a few moments, then just rested it on my right thigh. I looked over at him and smiled, our eyes locked and something within us both changed. We wouldn’t really understand it for a few months, and I will cover it more in the following post (I’ve written 8 pages in MS Word and still am not done – I need to seriously edit this story!!!), but our encounter today would ultimately change the rest of both our teenage lives. I grabbed his penis but I told him to give me a few minutes. Now that I reflect on this years later, I think I just wanted to truly be in the moment when I first pleasured Ben.
Well I finally caught my breath and I began to stroke Ben’s dick gently. It had been only semi-erect while we were relaxing but I could feel him almost immediately begin to harden. I can’t begin to tell you how anxious I was to worship his unit. As he became fully erect, I turned to him, looked him in the eyes and then began to settle between his legs. I continued to stroke him gently, without ever losing eye contact with him. He was beginning to breathe heavily as I did this and I slowly lowered my mouth to his head. My tongue danced around the tip of his head and I licked up the drippings of his pre-cum. I savoured the taste and appreciated the differences between Derrick and Ben. I began running my tongue up and down Ben’s shaft and began to sense that Ben was indeed better endowed than Derrick. He was probably an inch longer and while not dramatically, at least somewhat thicker despite being nearly a year younger. I closed my mouth around the head of his cock and began to bob the length of his unit. I could actually feel the head strike the back of my throat and I fought off the urge to gag. My tongue swirled against the underside of his dick and I could feel it continue to engorge. My eyes never left his and I could sense his breath quicken into ragged gasps as he fought the inevitable orgasm that was about to overcome him. I was desperate for him to shoot his sperm into my mouth but yet at the same time I wanted this to be his experience. I knew he was getting close when he started to talk. Ben has always been a pretty quiet guy ,but when he started to mutter things like “ God Jackie, that feel s so amazing, oh fuck, don’t stop” then moments later he started to literally shout “oh shit, I think I’m going to blow! Fuck, I’m cumming!!”. I clamped my lips down around the end of his penis and then maybe a second later felt his penis start to jerk. Whereas I was able to handle the volume of semen from Derrick, I started quickly to fall behind what Ben was putting out. I was swallowing probably every second, but I remember losing the battle after swallowing 4 times. Cum filled my mouth then overflowed past my lips down my chin and onto the upholstery of the sofa and onto the carpet below. Still he pumped two or three times more. I licked up what I could and then it struck me how much I liked his cum too. I filed that away quickly though as I panicked about staining the sofa and carpet as I knew my mom, cool as she was, would find this eventually and make for an awkward conversation between her and I. I grabbed a towel and a small bucket from the downstairs bathroom, filled the bucket up with hot water and began to wet down and blot up the stains.
That basically ended the first sexual experience I had with Ben and Derrick. The three of us would continue to explore each other over the next several week s of summer. I would have sex at least once or twice a week with both Ben and Derrick, often all three of us but sometimes just individually. I will make another post shortly to describe both my first vaginal and anal sexual experiences with both of them. I will definitely be more concise than I was today. I’ve written over 9 pages in MS Word, will keep it shorter next time! I will also post the two other major sexual milestones of my life down the road – the first time I had sex with a relative and the first time I had sex with a co-worker
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