Obsessed with big boobs

I’ve always been fascinated with women’s breasts. A nice ass, long legs and pretty face can always get my motor running but nothing works better for me than a tight top with lots of cleavage. In fact it’s seeing them encased in a bra, camisole or low cut shirt that excites me more than just a naked set of big tits. I constantly wonder what my cock would feel like between each set I see. I wonder what they would feel like in my hands and I want to see my seed covering them. I’d rather cum on a woman’s tits than any other part of their body which I’m know frustrates my wife sometimes.

I have been with the same woman for a long time and my wife has what most people would consider average size breasts. She knows I love breasts and she has certainly caught me on more than one occasion staring at other woman’s tits. I’ve tried many times to cum on my wife while she is still wearing her shirt but she always protested against it claiming that she had just washed it. I always feel that our sex is planned and contrived. It always the same basic love making and she doesn’t want to try new or outside the lines of just lying on the bed like a plank of wood.


I love my wife very much but my obsession was about to get me in trouble. Our office was developing a rather large marketing campaign and I now had to train two well-endowed girls straight out of University named Lynn and Sara. These two girls couldn’t be anymore unlike each other if they tried. Sara was Italian with dark skin, dark eyes, long flowing black hair and wore tight revealing clothing. For her first day of training she had on a tight short skirt, a deep cut blouse extenuating her cleavage with what seemed to be D size beauties. She came off as very confident, sexual and knew how to use her good looks to her advantage. If she was sitting she made it a point to have her skirt ride up to show the top of her stockings or if she was standing she always leaned forward to show off her large tits. It wasn’t difficult to get aroused when she was in the room.

Lynn for some reason was even more intriguing which was strange as she really came off very much a nerd. She looked like she had never been out in the sun she was so pale and I’ve never seen a woman in her 20’s covered up as much as she did. She wore dress pants that were too big, loose long-sleeved tops buttoned up right to the neck, glasses from the 60’s and what looked like orthopedic shoes. Her hair was short but had very little style which matched her personality. She was obviously not confident as she spoke like a mouse, fidgeted like a nervous wreck and was very clumsy. What was so interesting was the fact that she seemed to have double D size tits that were tightly squeezed into a bra three sizes too small just waiting to be set free.

As the weeks of training past, my fantasies went into overdrive. I would think about each set of tits individually and then start to wonder about them together as two pairs. I would picture both women on their knees side by side taking my cumshot as I would release my load in the bathroom stall at work. Sara acted like she knew I was jacking off to her as she would constantly walk into my office and put her hands on my desk to talk to me. She would even jiggle her tits for me as I tried to get quick looks at her beautiful tits.

We only had a couple of weeks until our deadline so we all started doing a lot of overtime. Lots of late nights eating pizza at our desks to try and get all the work done on time. We were certainly starting to get to know one another better and Sara and I started teasing poor Lynn trying to get a rise out of her. It turns out she led a pretty sheltered life up until now and the fact that she was a preacher’s daughter made me think she was very inexperienced. Sara and I started flirting a bit and any sexual comments would embarrass the shit out of Lynn.

One night it was just the three of us in the office as it was around 10pm. We were trying to finish up to go home and I asked Lynn to scan the last set of documents before we left for the evening. As soon as she was down the hall Sara came up close to me and whispered in my ear, “Have you jacked off today yet? Do you need some inspiration?” At first I was stunned but then I could feel my temperature begin to rise. “I don’t know what you’re talking about and I’m married thank you.” Now why did I say that?

“I don’t care if you’re married and I just want to help. You can’t blame a girl for trying can you? Besides for someone who jerks off so much, you sure as hell can’t be getting it at home.” Sara definitely had a point there. “I’ve seen you staring at both our tits you dirty bird. Don’t tell me you wouldn’t want to see my tits. Do you want me to show them to you?” Sara could see I was trying to avoid telling the truth but I had come to the conclusion a long time ago that if I ever did cheat on my wife it would have to be to fulfill my particular fantasies.

“There’s only one way that would ever happened.” I said to Sara in a shaky voice. “And that would be?” Sara asked with a smirk on her face. “Yeah, I don’t know if we can have that conversation and I don’t even know if I could trust you with that kind of information.” I explained. Before Sara could say anything else Lynn came back into the office. “All the files are scanned Mr. Roth. Anything else you’d like before I leave?” asked Lynn. Sara looked at me with a big smile on her face and I said, “Lynn, I told you to call me Jack, none of this mister crap ok?” Lynn blushed, lowered her head and whispered, “Yes Mr. …uh Jack sir. I’m sorry I’ll try to remember that.” And off she went.

There was no way I was going home tonight. I needed a drink bad. I sent a text off to my wife stating that I wasn’t coming home and spending another night on the couch in my office. She was used to me doing this around crunch time for campaigns and she texted me back to say “Don’t work too hard, call me in the am” I walked around the block from our office and hit my favorite sports bar to pound back a couple of drinks.

It was now 12:30am and I was feeling no pain. I finished what I thought was my last drink, set the glass down and then heard beside me, “Buy you another drink Jack?” I turned around to see Sara standing over top of me with her hands on her hips. “How did you know I was here and what are you doing here?” I asked with a sloshed accent. “I was taking a cab home from Finnegan’s bar and noticed your car was still in the parking lot. I figured you’d be here. Are you just gonna sit there or are you gonna ask me to join you?” Sara said. She seemed pretty drunk too.

I ordered another round of drinks for us and tried to make some small talk with Sara. Sara on the other hand wanted to get right to the heart of the matter. “So Jack, all I can think about is what it’s going to take to get you to tell me how this could happen?” I could tell Sara wasn’t going to let this go and I was feeling pretty brave and intoxicated. “What the hell. I have a thing for big tits.” I stated. “No shit, tell me something I don’t know.” Laughed Sara. “Well, there are particular things I like to do so, yeah but hmm…. I don’t know how to explain it.” I was struggling with my words. “Just tell me what you like Jack. I want to know.” Sara seemed really interested at this point.

“Well, I really like cumming on them but I also like it when, hmmmm, when the clothes are still on. Have you ever seen the category on porn sites that’s called Clothed Sex?” I had a hard time looking Sara in her eyes but she reached out and put her hand on mine and said “Go on, tell me more.” “Well, I really like it when they cum on a woman and they’re still wearing a shirt, bra, whatever and it’s all over their tits and clothes. I just think it’s really exciting.” “Now was that so hard to say?” laughed Sara.

“If that’s all you want then let’s go back to your office right now and you can cum on me.” Sara said all this with little effort. Now that I had her interest I thought I might as well go for broke. “Well if you can convince Lynn as well, then you have a deal.” I said with a smirk. “Now that might be a little tougher now wouldn’t it. I’ve known Lynn since high school and I have never seen her with a guy, ever. She’s not exactly what you’d call outgoing and it would take some doing to get you what you want.” Sara thought about it for a minute and then continued to say “Tell you what, you fuck me right now and I will get you the opportunity to cum on Lynn” “And how exactly will you get that to happen?” I asked. “That’s for me to work out. Do we have a deal?” asked Sara.

Within minutes of being back in my office, Sara and I were locked in a passionate kiss. Sara instantly grabbed both of my hands and placed them on her tits. I leaned back and took in the view as I felt all around her large tits through the silky fabric of her blouse. To be able to feel such a large pair of tits for the first time was everything I thought it would be. I stuffed as much as I could into the palms of my hands and I could feel her nipples poking through the fabric. Sara undid a couple of her buttons and I pushed her tits together and stared at her massive cleavage.

Sara reached down and began to unbutton my pants to let lose my eight inch erection. She cupped my balls with one hand and wrapped her other around my thick stick. She squeezed it hard and a drop of pre-cum drizzled out of the crown of my cock. Sara slid her finger across it and brought it up to her mouth to taste. “Ummmm, you taste good Jack!” she purred.

I reached into the fabric of her blouse and pushed it aside so I could see her red bra. It was so soft in the center with beautiful lace all around the edges. I brought my mouth down to her soft exposed skin and ran my tongue along it. Sara definitely liked this because she started pumping my cock with her hand. I ran my tongue all along her bra and up to her neck. I then reached into her bra and squeezed her nipple between my fingers. I slowly worked my tongue back down her neck while pulling her tit out of her bra. I hovered over her nipple with my mouth and breathed on it with my hot breath. I spit out a gob of saliva and dropped it on her nipple and continued to breathe over it for a couple of seconds. Then I opened my mouth as wide as I could and stuffed as much of her nipple in my mouth.

I sucked away at her tit and struggled to wet every section of such a large breast. I was in heaven and this was definitely the biggest tit I had ever tasted. Sara moaned away as I glazed her tit ferociously with my tongue and saliva. She had both hands pumping up and down on my shaft and she brought her lips to my ear and pleaded, “You have to fuck me now Jack. I can’t take it anymore. I need you inside of me now!”

I grabbed the back of Sara’s neck, turned her around and bent her over the front of my desk. With my other hand I lifted her skirt over her ass to expose her red thong underwear. I pushed it aside with my thumb and rammed my cock hard into her cunt. She was so wet that my thick cock slid in inch by inch until my crown pressed against the top of her inner wall. Sara let out one long grunt as I stuffed all of my cock into her. I held my cock deep inside of her, lowered my body onto her back and whispered to her, “Tell me how much you want me to fuck you.”

Sara groaned again and then pleaded with me, “Fuck me Jack! Fuck me hard!” With that she spread her legs more and gripped the edges of my desk with both of her hands waiting to be pounded. I began to slowly push my cock in and out of her swollen cunt while gripping her hips with both of my hands and holding her in place. Every time Sara tried to pick up the pace, I gripped her hips harder and held her down against my desk. “Jack, please give it to me harder. Fuck me harder!” she demanded.

After teasing her for a couple of minutes with my soft, slow thrusts, Sara looked back at me from over her shoulder with wild eyes and said through clenched teeth, “God damn it Jack. I want you to give it to me now, harder, harderrrrr!!!!” I felt she had waited long enough and I started to plunge my pelvis into her so hard the desk started to move under my power. I was like a man possessed pounding her as hard as I could. Her ass giggled with each thrust and you could probably hear the slapping of our skin down the hall.

Sara was now wincing with each thrust and she kept screaming, Yes, Yes, Yessss” All this time of having sex with the same woman unfulfilled had left me with a lot of pent up energy. My wife was more of a missionary no frills, lights off same day of the week kind of woman and now I was with a big tited young woman sprawled across the front of my desk at work in the wee hours of the morning pounding away like I have never been allowed to. The pressure in my nuts were telling me that I was close and it was the finish that I was most looking forward to. The image I constantly dreamed about.

“I’m close Sara!” I moaned. I pulled out of her and stepped back. Sara spun around and dropped to her knees. I took in the stunning vision that started from her legs enchased in panty-hose, her skirt pushed up and crumpled around her waist, one large tit pulled fully out of her blouse with the other in her bra with the blouse open. Sara held her arms open and raised her face to look me in my eyes. I was already jerking my cum covered cock and beating it with purpose. As I felt it build up inside of me I tried to hold it in as long as I could. With one long grunt I began to shoot my load. The first shot hit Sara’s face and hair. The second shot hit her blouse. The third hit her exposed tit. A couple more spirts covered her blouse some more with the remaining falling on her skirt and panty-hose.

I stood there for a good couple of minutes gazing at my seed all over Sara’s face, skin and clothes. I felt dizzy from the excitement of what had happened and what was kneeling before me. “Stay right there.” I asked. I grabbed my phone and took a few pictures of Sara which she gladly posed for. “You did your part Jack and now it’s time to do mine.” Smiled Sara.

Now Sara had a plan in place to invite Lynn to her apartment and get her drunk to loosen her up. “Now Jack, we are going to have to do this a bit at a time to get to the point where you can actually be there and hopefully get your fantasies fulfilled. What I can do for this time though is set up my webcam and you can watch from your office. I’m going to try to convince Lynn to try on some more seductive clothing and you can watch it all happen.” That sounded pretty damn fine to me.

I waited for what seemed like forever for Sara to turn on the camera from the computer in her apartment. I was starting to think this wasn’t going to happen. All of a sudden I receive a text from her saying that she is about to log on. I sat down at my chair and clicked the icon. Right away I’m hearing all sorts of laughter and Sara looking into the camera winking. She steps out of view and I can see Lynn sitting on her couch, a drink in her hand laughing uncontrollably. She appeared completely wasted.

“Lynn, I have known you for years and it’s time you started looking like a woman and getting fucked right proper.” The two girls burst out laughing again. “I don’t know Sara, I’m just not very comfortable wearing clothes like you, I would feel so naked.” Explained Lynn. “That’s because you’ve worn nothing but parka’s all your life. How’s anybody gonna see that beautiful body if you don’t show a little skin.” Shot back Sara. “I’m not as pretty as you are Sara and I don’t have a body like yours either.” “That’s not true and I’ll prove it to you.” Said Sara.

“Why don’t you try on some of my clothes and we’ll doll you up a bit Lynn. You’re about the same size as me I think except your boobs are a lot bigger.” Lynn went beat red with Sara’s statement. “You think you can make me look beautiful like you?” asked Lynn. “I know I can. In fact I’d bet you’d look stunning in some of my clothes. Let me top up your drink. You stay here and I’ll bring out some of my clothes for you to try on.” Sara left the room and I watched Lynn happily hum to herself swaying back and forth trying to keep her balance.

Sara returned from her room with a bunch of clothes which she threw onto the couch. “Now what should we try on first?” Sara seemed just as excited as I was. I was already rubbing my cock through my pants watching, wanting, waiting. “I don’t know, you pick something out.” Said Lynn. “Well first let’s get some of those clothes off of you so we can try some stuff on.” Said Sara. “I’m not sure I can do this Sara. I’ve never been undressed in front of anyone before.” Lynn was starting to panic a bit. “It’s no big deal Lynn, here, watch me. I don’t care if you see me. We’re just two friends trying clothes on.” With that Sara stood sideways in front of the camera and started to undo her shirt.

Lynn’s eyes went wide as Sara unbuttoned her shirt and pulled it out of her pants. Sara turned slightly, which I could tell she did for me and showed off her lacy black bra. Without asking Sara reached over to Lynn and started to unbutton at the neck of Lynn’s blouse. Lynn pulled back a bit but Sara pulled her forward and continued to work the rest of Lynn’s buttons. After she got to the last one, Sara tugged the bottom of Lynn’s shirt out of her pants and parted her blouse to expose Lynn’s bra.

Lynn’s tits were overflowing in her bra and Sara said to her, “We need to get you some new bras, this thing is way too small for you.” Sara ran her hands around Lynn’s bra to try and adjust it and Lynn gasped turning red in the face again. “Lynn, it’s no big deal, see?” Sara pulled her own shirt completely off and reached over to do the same to Lynn. She struggled a bit but quickly gave in and her shirt feel to the floor. Lynn had on a very large brown bra that was by no means frilly but I didn’t care. I couldn’t take my eyes off the screen at the site of those massive tits. Time to pull off my pants ?

Lynn was so nervous that she pretty much downed a whole glass of wine in one shot. Sara pulled her closer to her and their tits were now pressed up against one another. With wide eyes Lynn looked down at Sara’s tits pressed into hers in amazement. “Ok, let’s get your pants off next and then we’ll pick out some clothes to try on.” Instructed Sara. “You first.” Out of the mouth of Lynn. Sara smiled and wiggled her jeans off exposing her matched black thong. “My God, there’s hardly any material there.” Said Lynn. They both laughed and again Sara took the initiative and stared to undo Lynn’s belt synched around her waist. As soon as it was undone they feel to the floor because Lynn’s pants were so oversized.

“Jesus Lynn, those are granny panties you have on there.” I had to agree, there was a lot of material there covering Lynn’s ass but at the same time it was still pretty exciting. Sara reached down to the pile of clothes on the couch and picked up a pair of panties. Lynn shook her head no and asked, “Do you have anything with a bit more material? I’m not shaved like you are.” Sara smiled and picked up another pair and waved it at Lynn. Sara then dropped to her knees and started to pull Lynn’s underwear down to her feet. Lynn was very bushy and I was intrigued that Sara seemed to hover inches away from Lynn’s snatch.

Lynn stepped into Sara’s panties and Sara worked them back up to Lynn’s waist and cupped both her ass checks pretending to adjust them when it was pretty clear she was getting in a good feel for herself. “Those look nice on you Lynn” stated Sara. Lynn looked down at herself and seemed pretty pleased with what she saw. “Now I have this very cute long skirt that I think would look great on you.” Lynn obeyed and put it on. Then Sara handed her a cotton scoop neck t-shirt with no sleeves. Lynn pulled it over her head and the shirt hugged every part of her body. Lynn’s tits looked huge wrapped in the thin cotton. She seemed somewhat skeptical and downed another full glass of wine.

“Now let’s do something about that hair.” Sara pulled out a chair and placed it right in front of the camera. “Sit here and I’ll get some hair gel.” Lynn looked down and checked out her whole body while Sara was gone. Sara still wearing only her thong and bra, stood behind Lynn who was sitting in the chair in front of me and started to put gel in Lynn’s hair. Sara removed Lynn’s glasses, took a brush and combed all of Lynn’s hair back. What happened next almost made me blow my load right then and there.

Sara started rubbing Lynn’s shoulders, looked directly at me in the camera and smiled. Lynn’s eyes were closed and she was swaying a bit in the chair. Sara started to run her hands down the top of Lynn’s exposed skin on her breasts and then she leaned over and cupped both of her tits. Lynn’s eyes jolted open, “What are you doing??” “Sshh, just go with it. Let me show you what it can feel like to be a woman.” Lynn started to squirm in her chair but Sara continued to play with her tits. Slowly Lynn started to calm down and I’m sure being so drunk was playing to Sara’s advantage.

Sara reached into the back of Lynn’s t-shirt and unclasped her bra. It was obvious Lynn’s bra was very constraining because I watched her chest size expand even more. Sara then reached into the front of Lynn’s t-shirt and cupped one of her tits. No resistance from Lynn this time. Just a soft moan. Sara looked up at me through the camera as she played with Lynn’s tits.

Sara reached down even further from behind Lynn and pulled the material of her skirt up to her waist. I could now see Lynn’s panties plus an awesome view of Sara’s tits hanging over Lynn’s shoulders. She reached down and ran a couple of fingers over Lynn’s panties. “Stop, I don’t think we should do this. It’s wrong, you’re a woman” pleaded Lynn. “Who better than your best friend to show you what it could feel like. Let me show you how nice this can feel.” Responded Sara. She pressed two fingers hard into Lynn’s panties and Lynn let out another groan.

Sara grabbed Lynn’s face and kissed her hard. I had to let go of my cock or else it would have been all over for me. I watched them kiss some more, tongues swirling and Sara’s fingers working Lynn’s soaked panties. Lynn had now lost all inhabitations as she spread her legs more to give Sara’s fingers more room to dig. Lynn reached up with her hand and wrapped it around Sara head and kiss her deeper. I could see everything perfectly in front of my computer screen and the view was breathtaking.

Sara knew what she was doing and what it would take to bring Lynn along to a heightened state to make her next moves. Sara released her lips on Lynn, pulled out one of Lynn’s giant tits and moved beside her. Lynn’s eyes followed her the whole way as Sara took Lynn’s tit in both hands and stuck her mouth directly onto Lynn’s nipple. Lynn threw her head back as soon as Sara’s wet mouth touched her skin. Sara sucked Lynn’s tit and then run her tongue along it like a dog lapping up water. She continued and watched Lynn’s face as she was quickly becoming lost in pleasure.

Sara pulled her own thong off her body, stood up, looked Lynn in her eyes and said, “Pull off your panties.” Lynn obeyed without hesitation but stayed on the chair. “Show me how you touch yourself.” She continued. Lynn ran her hands down her body towards her swollen cunt but Sara stopped her. “Touch mine not yours.” Demanded Sara. Sara moved in between Lynn’s right leg and Lynn slowly reached up to Sara’s parted legs and stuck her finger between Sara’s cunt lips. Lynn looked into Sara’s eyes for approval to ensure she was doing it right. “Put your fingers in.” moaned Sarah.

Lynn did as she as was instructed but she didn’t move her fingers once inside Sara’s wet cunt. “Like this Honey.” Sarah reached down, pushed two fingers into Lynn’s cunt and began to finger fuck her. Sara was gentle to start as it was probably the first time anyone had done that to her. Lynn’s eyes went wide again with the new sensation between her legs but once she regained her composure, she started to mimic the finger movements herself.

Sara wisely let Lynn determine the pace. She knew once Lynn was ready, she’d pick up the pace herself. She wanted to make this a totally enjoyable experience and not frighten her. Gradually Lynn became more relaxed so Sara decided to stick a third finger into her hot wetness. Lynn mimicked Sara’s move and soon fingers were sloshing in and out at a quick pace.

Sara could tell Lynn was on the verge of climax so she leaned forward, grabbed Lynn’s big tit with her free hand and searched out her clit to finish her off. I wrapped my hand around my throbbing cock and began to pump it again.

Once Sara had found the magic spot on Lynn, she twirled and pinched at it until Lynn couldn’t take it anymore. She began to shudder and her juices spilled out of her onto the chair and Sara’s hand. Lynn continued to shove her fingers in and out of Sara trying to give her the same pleasure. Sara reached down and played with her own clit as Lynn pumped her fingers into her. I stood up from my chair and released gobs of semen all over my desk. I watched Sara start to convulse herself as her own juices started to run down the inside of her legs.

All three of us stood motionless panting from this spectacular experience. Lynn cumming for the first time under the power of another woman, Sara being brought off by her best friend while knowing I was watching from my computer and for myself, the most exciting thing I had ever witnessed in my life. I was also excited because I knew there would be more to come and I am very hopeful that I’ll get the chance to cum all over these two sets of big tits.