This story is about my first big cock. I am on the shy side and generally conservative. I guess I can be described as a professional woman. I have been with my fair share of guys but I have never been with a guy who was hung. I have a twin sister (we are not identical) and she was bragging about a guy she was seeing and how great the sex was because he was hung. My sister is the wild one and has been since we were teenagers. I have been seeing the same guy for over a year now and he could be the one I end up marrying. I have been thinking a lot about marriage and I felt like I should at least have a similar experience as my sister before I settle down. I guess my sister’s comments really got to me. Having been with a dozen or so men you would think I would have gotten lucky that way. After my conversation with my sister, I started watching a lot of porno videos of hung guys and it really was turning me on. Over the course of the next few weeks it had become an obsession. I knew I had to satisfy my curiosity. I did have an upcoming work trip to Boston. I figured that may be a good time because I would be away from home. I could have a one- time fling in the privacy of my hotel room with a guy I would never have to see again. That part of the plan seemed perfect. Hmmmm, but how do I find a guy to meet my “qualifications”? I didn’t want to leave it to chance.
So I decide to write an ad on Craig’s List. The ad went something like this:
First off, I am new to this. About me: I am a 30 year old female. I am 5’ 3” 120 lbs brown hair and blue eyes. Guys hit on me a lot so I guess fairly attractive,lol. So why am I posting here? I have been having a fantasy that I want to act on. I have never been with a well endowed man. I have a steady boyfriend so I am only looking for some no strings attached fun. This would be a “one- time only” fling for me as I am on an upcoming business trip the second week of November. My ideal man would be between 35-40, white and married. NO PLAYERS!!!. Your face picture gets mine in return.
As you can imagine, I got a bunch of responses. I didn’t realize how many horny guys there are out there…lol, although most of them didn’t even fit my request for a white guy between the ages of 35 - 40. After a couple days, I finally got one that interested me. His name was Steve and his written response was polite plus his face picture was attractive. He was good looking with blondish hair and looked to be the rugged type. He said he was 37, 5’ 10” and 195lbs. He was married and that this would be his first attempt at an affair. He had been married for 10 years and just recently decided that he would look to have some fun. I liked this since it seemed he wasn’t a “player”.
I responded back to him saying I liked his email and picture. I let him know I was interested and sent him my face picture. I wrote that if he thought I was attractive to let me know. It didn’t take him long to respond back. He thought I was a real “hottie” (his words not mine) and that he was flattered that I found him attractive.
I guess I should describe myself a little better. (I know when I read these stories I like the descriptions). I do work out so I am in decent shape. I am toned, my butt is a little on the big side (at least I think it is) but is also very solid. I do have freckles on my face and body. My hair is thick, brown and shoulder length. I have a nice complexion and tan easily. I have average sized boobs, 32C.
He wrote, “What is the next step?” I responded by asking him if I could see a picture as proof that he was indeed well endowed. I have to admit that it was very exciting waiting for his return response. It didn’t take too long. When I saw that there was an attachment my heart started to race just a little. He sent me 4 pictures. He had a good solid build. In the pictures, I could see that he had a really nice butt and that he indeed did have a pretty big dick that looked to be fairly thick as well.
I responded back by saying he definitely meets all my requirements . I told him that I wanted to exchange emails and get to know him first. It was important to me that he knows that I was not some slut and that this was really just me experimenting. I also wanted to be careful. Besides the physical attraction, I wanted to make sure we were both on the same page. We ended up exchanging emails for about two weeks. We would ask each other various questions. That in itself was a real turn on. I couldn’t wait to get the next email. I was happy to find out that he had been faithful to his wife and that I would be his first. I didn’t want a player and I certainly didn’t want to pick up any diseases. I let him know that if we do hook up that we will need to practice safe sex.
During those email exchanges, I found out that he can last long and can go a few rounds, as he put it. My current boyfriend lacks in both those skills so as you can imagine that was another big plus. It was interesting to hear the questions he had for me as well. He asked me about my” grooming habits”. I told him I was completely shaven. He said that he was hoping I would be. He asked about my orgasms. I told him that it takes me a while and that I only orgasm when I guy goes down on me for a while. I also told him I never had multiple orgasms during a love making session. He said he’ll take it as a personal challenge to change that. I did end up sending him more photos of me. I had a few sexy ones that were taken of me in a club. He wanted nude pictures but I told him sorry but I wasn’t going to do that. He said it was a turn on for him that he would be my first big one. He said that when he was single he use to love that first time a girl would see it just to see her reaction. He asked me if I had any questions for him. I said not really (I did but I felt funny asking him).
After a couple more email exchange, I finally got the nerve up to ask him. Does it always fit? I told him that guys have told me I am very… tight…. and that…well...they weren’t as… gifted as him. Again, I couldn’t wait until I got his email response back.
He said that he had never been with a virgin but that depending on the girl it could take a little getting used to. He went on to say that before he was married, he did have sex with a girl he meet on a cruise ship when he was on vacation. She was also very tight and that they started and stopped a few times. Although at first she was a little “uncomfortable” after a while she loved it. He said not to worry that he would be gentle and go slow until I was comfortable with it. His explanation made me feel more reassured that this guy would be perfect for me. We agreed to meet at the hotel bar on the 2nd day of my trip.
The time couldn’t go by quick enough. I had fantasies every day. I would look at the pictures he sent me and watch porno every evening. I would always look for the big cock ones and always imagine myself in the girl’s place. Those big, beautiful hard cocks . I even found videos of girls having their 1st big cock experience. A few of the girls did seem uncomfortable but they all seemed fine and well satisfied in the end. I couldn’t wait!!!
I was so nervous meeting that evening. I really am shy and this was definitely out of character for me. In fact, I even thought about cancelling it. I didn’t of course, but I was so nervous.
I wanted to look classy and attractive for him without looking “slutty”. I decided to wear a nice beige fitted sweater with my long brown skirt. I had always gotten compliments when I wear that outfit. Of course I decided this a week before I had to travel…lol. I had also decided to wear a black push up bra that was slightly padded with matching French cut panties. I looked in the full length mirror right before I went down to the bar. My figure really looked great in this outfit. I looked nice and curvy and shapely. I was sure to make a good first impression when he saw me. I took a deep breath and said to myself, “I am really going to do this”.
I sat at the empty side of the bar and ordered a glass of white wine. I needed something to calm my nerves. He wasn’t there yet and my mind was racing with all kinds of thoughts. What if he didn’t show up? What if he was a jerk? Should I just forget about it? What was I doing here waiting to meet a stranger? Luckily I wasn’t quite finished with my drink when he walked in the bar. I really don’t know what would have happened if he had been much later. I was having second thoughts so much so that I was thinking of finishing my drink and leaving. We recognized each other right away. Steve sat down next to me and introduced himself and shook my hand. He ordered us both a drink. We exchanged small talk for about the first 20 minutes. We both agreed that another drink was in order before we headed to my room. He admitted to me that he was nervous and we both laughed when I said “Me too, glad I am not the only one”.
Steve had a nice personality and made me feel really comfortable as he had a good sense of humor. He complimented me a lot. He said I looked even better in person. He even complimented my outfit. “You are very sexy and a real hottie”, he said. That did make me smile and laugh. He was certainly a charmer. We then started to talk about some of our email exchanges and he asked if I was still worried about the “fit thing”. I felt kind of embarrassed and said no then quickly changed the subject.
He finished his drink before I did and asked if he should order another or was I ready to leave. I took a deep breath then finished the last bit of wine in my glass. I was feeling pretty good (3 glasses of wine does that to me). I stood up and off we went. As we got on the elevator, I was thinking to myself wow, I am really going to do this. I was kind of proud of myself for not letting my usual shyness stop me. My heart was racing as I opened the door to my room.
I was putting my purse and room key on the desk when he surprised me by putting his hands around my waist. He wasn’t wasting any time which was probably the best thing for me at that point. He squeezed my waist and said “Your ass looks so good in that skirt”. He turned me around and softly kissed me on the lips. He then whispered in my ear, “I can’t wait to get you out of those clothes”. He kissed me again but this time it was more intense and passionate. As he was kissing me he started to pull my sweater up and eventually over my head. We kept kissing as he threw my sweater on the chair. He then pulled me in really close to him as his hands went down to my butt. He was squeezing both cheeks of my butt and it was all so exciting. Here I was in a hotel room with a stranger about to have sex with a guy who was cute, built and hung.
I made the next move and pulled up his sweater over his head. Since he was still squeezing my butt, I figured I might as well get a feel myself of his butt. His next move was to take off my long brown skirt. I helped him of course by first flicking off my shoes and wriggling out of my skirt as I tossed it on the chair. He stepped back a moment to check out my body. He said, “You are so sex, I really dig the black panties.” We embraced and started to kiss again. He was back to squeezing my butt and also just rubbing my back lightly as we were in a deep kiss.
When we broke the kiss he put his hands on top of my shoulders and looked at me. I knew what he wanted that very second. It was what I wanted too. So I lowered myself slowly and got on my knees. I loosen his belt and looked up at him. He looked down at me and just grinned. I then open his jeans and slowly pulled down his zipper looking back up at him. I pulled his jeans down slowly being careful to make sure his boxers stayed in place. This was like a Christmas morning and I wanted to enjoy the suspense and revel in the anticipation of my “present”. At that moment, I was thinking about the pictures he had sent me. I then slowly pulled down his boxers and out sprang my “present”.
He was only semi-hard but it still looked impressive. I admired it for a moment before I took hold of his magnificent cock in my hand. It really was a good looking cock. I started by wiggling it in my hand from side to side just to feel the weight of it in my hand. He said “So, what do you think”? I replied, “very nice”. I then started to pull and jerk his cock as I held him captive right behind his pretty dick head. I could feel it starting to come to life and grow. I circled the head of his cock with my stuck out tongue. I was looking up at him to see his reaction. He just let out an ummmm sound and I knew he approved. I focused on the area right under the head and wiggled my tongue back and forth. He let out with an “oh yeahhhh baby”. I then put the whole head in my mouth and I could feel the warmth. I circled my tongue around his head while keeping it in my mouth. I then started to move my hand gently up and down the shaft while alternately sucking and licking his cock head. He was now hard as a rock. I stopped for a moment to admire the effect I was having on his manhood. That is when I said” Oh my god, your cock is really big”. Now don’t get me wrong it wasn’t one of those monster cocks. It was just a nice big thick cock. Seeing pictures is one thing but having it right in my face was a whole other story. It was impressive and I couldn’t wait for him to put it inside me.
During our email exchanges he told me he likes to “shoot his first load” and then take care of his partner. He said because then when she is ready, I am too. So I had him lay on the bed while I kneeled on the floor at the base edge of the bed. I went back to work on his swollen cock. I started up again by licking his shaven balls (another thing I like) while pumping his cock slowly with my hand. He said ”That feels awesome baby”. I had watched so many pornos and this was my version of the “best of blow job scenes”. I would lick slowly up the shaft then suck on the head before returning to lick his balls. I alternated doing this for a few minutes. After that, I decided I wanted to see how much of the fat cock I could take down my throat. I have a pretty small mouth and I do gag easily. I could only fit about 3 inches down in my mouth. I then picked up the pace a bit by bobbing my head up and down at a quickened pace. When I did take my mouth off, I would use my hand and admire his firm, wet, hot cock. All the while I was thinking about how it would feel when he was pumping it into me. At one point, I found myself rubbing my pussy through my panties, God I was so wet. I guess I was impatient so I went into “make him cum as soon as possible” mode. My pace picked up. I found myself saying, “Oh, I love your big cock”, and I was making popping and slurping noises for that extra effect (I picked that up from all those pornos I watched). It didn’t take too much longer before I heard him say he was going to cum. I pointed his cock up towards his face as I jerked him fast and hard he started to cum while yelling out “ohhh yeah”. I kept jerking him off until I saw no more cum spewing out. That is when I put the head of his cock back in my mouth and circled the head with my tongue driving him even more crazy as he twitched and yelled out one more “Oh yeah baby”. Being the nice girl I am, I went into the bathroom and got a nice hot towel to clean him up.
I laid next to him on the bed all proud of myself for giving him a great blow job. He started to kiss me and then whispered in my ear that it was my turn. He was kissing me when his hands started to roam over my body. His touch was gentle and sensual. He started to lightly rub his fingertips over my bra circling my nipples over the fabric of my bra. He then lowered my bra straps and with his fingers was tweaking my nipples which were now very aroused. Next he took off my bra. Then his tongue quickly found my nipple. He was circling my nipple with his tongue and alternating each breast. He would also use his fingers and pinch my nipples. He seemed to love to squeeze by breast with his whole palm. While he was sucking on my nipple his hand slowly made its way down my stomach until his hand rested on panties. He was rubbing me through the fabric. He whispered in my ear, ”Good you are nice and wet”. His hand then went inside my panties as I spread my legs to give him access to my aching clit. He rubbed me that way for a few minutes as he knew he had my approval by my low moans.
He then kissed his way down my stomach. His hands eased off my wet panties and he threw them to the floor. He pulled me to the edge of the base of the bed and got on the floor, in the same position I was when I went down on him. He spread my legs and dove in with his face. He started by slowly licking my outer pussy lips but it didn’t take long until he was licking my clit up and down with his hot tongue. I was really enjoying his tongue skills so much so that I wasn’t even thinking about that big cock of his. He would alternate between intense licking and light sensual licking and it was driving me crazy. I was moaning softly and mmmm’ing and ahhh’ing. He stopped after a while so that he could “see just how tight my pussy really is” as he put it. Upon inserted his finger inside me he said “hmmm your pussy really is tight, you weren’t kidding. I am so going to enjoy breaking you in”. Then he stood up and told me not to worry that he was just going to rub his cock on my pussy. I actually love when a guy does that as part of foreplay. I propped a pillow under my head so I could watch. His cock was soft when he took it in his hand. He started to rub his beautiful bulbous cock head on my pussy. I could immediately feel the warmth of his cock. He would rub it in both directions, up and down and left to right. He would slowly jerk off making his cock bigger and harder. He then placed his cock on top of my pussy and holding my pussy open, he began to move his hips in and out. Just seeing how far his cock rode up my stomach was a turn on. This was so hot for me to watch as I could see his cock expanding and becoming rock hard. He was really making me hot and lustful. Then he held his cock in his hand as he moved his enormous head back and forth over the opening of my pussy. It felt so good, I was going out of my mind. “Oh god that feels sooo good”, I said. Right after I said that, I could feel his cock head starting to exert more pressure on my pussy opening. I knew he wanted to insert himself into me. Even though it felt incredible and I was going out of my mind, I had the presence of mind to ask him, “put….mmmm….. on….. a condom”. He said, “Baby, I will in a little bit, trust me. Your pussy is so tight. Let me just loosen you up a bit before I put it on, ok?"
I did understand what he meant so I just said ok. He asked me for a pillow and he placed it under my butt. He held his cock in one hand while his finger found my tight pussy hole with the other hand. Soon I felt the pressure of his cock head on my pussy opening again. He was slowly going to work that big hard cock into me. At that moment, I remember thinking that I was finally going to be fucked by my 1st big cock. I could feel and see him hitting a little resistance. He would just retreat and try again. When he got the head in, I could already feel the girth that I so craved for. Next came the slow push forward as I let out an “ohhhhhh” He asked if he was hurting me. “No” Should I keep going going? “Yes” as I bit down on my lip. He would pull back and slowly thrust back into me. He wasn’t making much progress. He said, “This is one tight pussy”. He increased his thrust and finally my pussy let him in a little further. “There we go, good girl” he said. He would go back and forth, thrusting into me but not trying to go any deeper. I guess he was letting me get use to him slowly. “Mmmm”, was my response with each thrust. Honestly, at this point I was in a little discomfort. I think he saw it in my facial reactions. I could feel myself being split open wider than ever and he was only a few inches in. Then came the next inch of cock. “ohhh” another inch “ohhh, “My God, your cock is so big” “You want me to stop?” he said. “No” I said in between my panting. I looked up and it was a just little more than half way inside me. In and out he rocked for a few more strokes before he pushed in even further, backing out then slowly back in. He was being gently with me. “There baby just a little bit more to go” he said sympathetically. “You want more of my cock don’t you?” “Yes” “You sure you can you handle it?” “ah huh” He lunged forward this time he wasn’t going to be denied. His thrust his entire thick 8 inch cock into me. I let out a long, loud moan. I could feel him inside me. He was completely inside me. As he just held his position deep inside me. I felt myself being stretched and that he occupied every inch of my cavity. He pushed the pillow out from under me and lowered himself down to my face and gave me a peak on the forehead. He whispered in my ear, “Now we are going to fuck”. I just looked at him as we were face to face, caught my breath “Oh”, bit my lip, “Ok”. He said, “You little sex kitten”. He put his face next to mine and withdrew most of his cock only to slowly bury it to the hilt. Each time he would grunt in my ear and I would have a low moan back into his. We alternated like this for a while. Each time he would pause and I could feel my cunt muscles contract and tighten squeezing his 8 inches of man meat. He said, “I think your pussy likes me”. Then when he was fully inside me he pushed harder, moving me up the bed. His grunt got louder and my moan changed into a loud, long “ohh”. We were going back and forth seeing how the other would react. Slowly out and slowly in and another thrust even harder lifting me further up the bed. His grunt was louder and my matching response “ohhhhhh” was louder”. Again and again, I would catch my breath in between thrusts waiting for the next one. I had never been fucked this way before. Eventually my head was hitting the headboard on each thrust. It was slow but forceful.
He got up and as he took his cock out of my pussy it let loose of the trapped air. (I always feel the need to apologize when that happens). He pulled me down towards the edge of the bed and put the pillow under me again. He grabbed my legs and spread them apart, one on each side of him. He took a hold of his cock and guided it back into my eager pussy. His cock was met by a lot less resistance from my pussy this time. A couple of in and out hip movements as he was working his cock back deep inside me. Holding my legs open, he began with a steady slow pace. I think he was just making sure I was still ok with everything. Right after that he heard me say “God this feels so good”. He started to pick up the pace. His fucking pace quicken but was still steady. I closed my eyes and started to let myself go more than I ever have. Looking back, I think the 3 glasses of wine helped to relax me. He started to talk to me,
“Melinda, you like fucking me?”
“Oh yes, Steve. It feels so good. Your cock feels soooo good” mmmmm
I think at that moment he knew I was his. He knew he could have his way with me.
He started to jackrabbit me (at least that is what I call it). He would go real fast for 6 strokes then slow down. The change of the pace was getting to me. “Oh yeah, oh yeah, oh fuck me Steve” He kept changing the pace and I kept moaning. I was getting louder with each round of fast pace fucking. It was totally out of character for me. I am never that vocal. All of a sudden he doesn’t stop after the sixth stroke, he just keeps the fast pace. “Ohhhh…… ohhhhh…. ohhhhh God, Steve I am gonna cum, fuck me, don’t stop, fuck me Steve”. Steve now plunges his cock deeper into me, our bodies slapped together with each thrust. I was cumming, I was cumming for the first time during intercourse. As I was cumming, I was really loudly “Ohhhhhhhhhhhhhhhh’ing” during the intense orgasm. My body was twitching as he kept pounding into me. Sensing I was done and needed a break, he stopped and got up. Standing at the side of the bed next to me he asked me to clean off his cock. I reached for the towel but he said “No, I mean with your mouth”. I had never done that before and it occurred to me, I just fucked a total stranger and he wasn’t even wearing a condom. In all the excitement I must have forgotten. I am on the pill but still I usually play it safe. I had seen it done in pornos. I guess I was a little drunk plus I just came off a great orgasm so I figured what the heck. I mean girls seem to do it in many of the pornos I watched. I grabbed his cock and guided my mouth on to his pulsating cock head. I gently circled the head with my tongue. Sticking out my tongue and teasing him with my slow movement as he looked down at me. I kept looking up at him. (I like to watch a guy’s reaction). I then licked the shaft until I went all the way around. I started to jerk him while bopping my head down on his cock. I thought he was ready to cum. After about a minute he stopped me. He asked me if I like doggy style. I said “yeah, sure”.
With that he joined me on the bed. I got on all fours as he knelt on the bed behind me. He started by rubbing my butt with his hand ever so gently. He said I had a nice butt. He then reached down and found my pussy opening and guided his big cock into me. He was slowly inching into me. I was looking under me watching his balls coming at me as he eased into me. This time he didn’t go in and out but rather just applied enough pressure to slowly slide into me. Once he was all the way in, he put his hands on my hips.
He held me steady as he moved his own hips back and forth. My low moans began immediately letting him know I approved. He started slow, easing in, stopping, then slowly easing out. It felt so good. He just stayed at that steady slow pace. We were in this position for about 5 minutes. He asked me if I wanted to change positions and get on top. He laid flat on the bed as I happily straddled him. I grabbed his swollen cock and guided it into me slowly easing my way down. Each up and down motion I would take in a little more. He immediately put his hands on my tits. He was playing with my tits as I slowly rode him. I then leaned over him so he could suck on my tits as I rode him a little harder. He put his hands on my hips and pushed me down on him controlling the pace. “You like fucking me don’t you?” he said. ‘Oh Yes” was my reply. I really was having the best sex of my life. We then switched positions again. This time I was on my knees at the edge of the bed. Steve was standing behind me. I had my butt in the air and my head was on my folded arms on the bed. Once he was inside me he wasted no time fucking me faster and harder than before. With each hard pump, I would instinctively let out an “Oh”. In “Oh”, Out breath, In “Oh”, Out breath In “Oh”, Out breath and so it went. I could feel another orgasm coming on. “Oh, Oh, Oh fuck, Oh, Oh,” He put his foot on the bed next to me so he could get more leverage. He was now fucking me as hard as he could. Our bodies would make a slapping sound with each thrust. I could feel his ball hitting my ass. “OH, OH, Oh yeah, OH, OH, OH GOD I AM GOING TO CUM, OHHHHHHHH”. He kept pound me as I had my orgasm. When he knew my orgasm had passed he slowed the pace down. Then he started pounding into me up again. Oh Melinda, I’m going to cum. “ Oh, Oh yeah”. He pulled out of me and I could feel his hot cum squirting on my lower back. After he caught his breath he returned the favor and cleaned me up with the towel.