0 comments/ 27658 views/ 1 favorites My First Real Man By: dystopia As I type this, Michael's sleeping. His fuzzy chest expands and contracts with each breath. I'm sitting Indian-style, perpendicular to him, with my computer on my lap. My back's against the cool smooth plaster wall. A cool breeze is coming through the open window to my left. His cum is seeping out of me. I've never had sex like I had tonight. Sure, I'm only 19, but I've been with a few guys. I felt like I knew what I was doing, but with Michael I quickly realized that I had only been with boys. Michael's a man. He's 27, and he said I was the 13th girl he's slept with. Lucky 13. I don't think that's too many for someone his age. Frankly, I figured he would've been with at least twice that many girls. He's so cute and charming. I just assumed he got laid all the time, but he said, "It's one of those deals where when it rains, it pours." He said he hadn't had sex in six months. He said he had a lot of frustrations and that he was going to take them out on me. He most certainly did that. I'm going to be really sore tomorrow. I met him at Larry's party last week, but apparently he was blacked out when we talked. I didn't know that until I ran into him yesterday at Angel's Café. I went there get my caffeine fix and work on an article I'm writing for a web site that provides sexual advice to teenage girls. He was sitting in the back, drinking a double espresso, and drawing in his sketchpad. He's a comic book artist, and he's really good. You might've seen his one book, Hate World. Though I guess it's kinda underground. He doesn't make much money from it so he works part-time for a local book publisher. Anyway, I got a coffee and asked him if he minded if I sat down. I felt so stupid when he didn't even remember me. But he was really nice, though, and he apologized over and over again once I told him about Larry's. I about choked on my coffee when he asked with obvious concern, "We didn't, like, do anything, did we?" I assured him it was all good and clean. We talked for a little bit, and then he invited me back to his place. He lives with a girl named Kimberly, who just turned 21, and is apparently the younger sister of one of his best friends from high school. She wasn't around, though, and from what Michael said, she goes home a lot with boys she just met. Whatever. As soon as we got to his place, he pulled out a blue glass bong and packed a bowl. I don't smoke pot on a regular basis, but I'm not afraid of it, either. It must've been strong stuff because I got higher than I've ever been before. We sat on the couch, passed the bong back and forth, and listened to the Deftones, which definitely earned him bonus points because they're one of my favorite bands. If the song "Passenger", featuring Maynard James Keenan from Tool, doesn't get your juices flowing then you're not alive. I asked him if he thought it was weird to be hanging out with someone so much younger than him, and he said it didn't matter to him one way or the other. We have so much in common and the conversation flowed so nicely that it seems like we've known each other for years. He suggested that perhaps our souls knew each other in heaven before we were born. He says the most beautiful things. I told him he should write, but he said he prefers to draw. I really don't know how it got started, but somehow we just started making out on the couch. He's such an amazing kisser. He made me feel like we were in a movie. I don't know if it was the weed, or maybe I was just horny (OK, I was definitely horny!) but I was the one who made the move that escalated things. I couldn't help it. I wanted him so badly. So while we were kissing I put my hand on his thigh and slowly worked my way up his shorts. He was semi-hard and I quickly determined that he had a nice package. There's nothing worse than that moment after you're getting down to business with a guy and the pants come off and you're like, "Ooh, that's a disappointment." I didn't have that problem with Michael. Once I started feeling his dick, our clothes came flying off pretty fast. In fact, we left a trail of clothes leading back to his bedroom. When we got into his room we stood there naked, in a tight embrace, and practically devoured each other with kisses. He was sawing his broad cock back and forth against my already sopping lips. He leaned down and alternately suckled each of my stiff nipples and bit them playfully. That got me so worked up I dropped to my knees and started sucking his dick. He was like throbbing steel by this point. I couldn't get my hand around his dick without squeezing really hard. It's about as big around as my wrist. What surprised me even more, though, was how big his balls were and how far down they hung. I never saw such a pair. I couldn't help feeling their heft and lightly playing with them. He loved that. I sucked him off pretty good for awhile but then my jaw started to hurt. As I went to stand up he gently pushed me back onto the bed, knelt down, and started eating me out. He had me orgasming in minutes. He was massaging my g-spot with two fingers and licking and sucking my clit. My juice was just pouring out. I muttered something about ruining his sheets, but he didn't care. He made me cum twice that way, and then I told him I had to have him in me. I think he was about to get a condom when I informed him that I was on the pill and that it was all good. I know most guys hate condoms, and he seemed pretty happy when I told him he didn't need one. I started to scoot back in the bed to make room for him, but he grabbed my hips, leaned over, and in the sexiest voice said, "No, I want you right where you are." He then pulled me so my ass my just barely hanging over the edge of the bed. I lifted my legs for him and watched as he began pushing into me. Even though I was absolutely soaked, it still took him some effort just pop the head in. Then he slowly plunged all the way in. His dick pried me wide open. That was the first time I felt pain during sex since I lost my virginity two years ago. He took a hold of my ankles and slowly withdrew until just the head remained in my steaming clutches. He continued the long strokes, but he sped up each time. Soon he was vigorously pistoning in and out. I was getting juicier and juicier. His pendulous nuts slapped obscenely against my ass. After not too long, I grew tired of holding my head up to watch, so I laid back fully and just enjoyed the sensations. Right after I did that he decided it was time to switch to a more conventional arrangement. I nearly swooned when he pulled his dick out with an audible pop. The sensation of him withdrawing reminded me of pulling the plunger out of a syringe. Nobody had ever filled me so completely. He wasn't too long, either, which was nice because it meant he could really wail away without hurting me too much. I don't mind some pain but I don't need to feel like I'm being skewered. Instead of being stabbed I felt like I was being opened up and massaged from the inside. I'm getting aroused just writing about it. Anyway, he climbed atop me, grinned, and drove it home with one strong languorous push. He held himself up with his muscular arms as he pumped away. Another orgasm exploded from my pussy, blazed up my spine, and finished with fireworks in my brain. I thought I was going to pass out. The edges of my vision went blurry, and I think I was hyperventilating. He began breathing heavy and muttered that he was getting close. He kissed me lightly on the cheek and told me he was losing his mind. He increased his speed and force even more. My whole body was quivering. It was like I was having one giant streaming orgasm. I pulled him down and wrapped my legs around him. He threw himself against me again and again like he was trying to kill me. Suddenly he grunted, "Fuck!", and he began convulsing and grinding his pubic bone against me. I could feel his hot semen jetting into the depths of my vagina. He seemed to cum forever. He continued grunting and grinding for quite some time before he finally relaxed. We kissed passionately and he gasped, "That was incredible." I agreed wholeheartedly. He withdrew his rapidly withering erection, rolled over, and collapsed beside me. Both of our bodies were totally sheened with sweat. He lightly traced a finger around my straining nipples. He smirked and noted that my chest and face were flushed. All I could say was, "Michael, you really went to town on me." That earned me a huge smile and another passionate kiss. He said he couldn't have done it if he hadn't had such a beautiful and amazing partner. Then he added that I have a "fantastic pussy". I told him he was naughty and gave his slimy dick a squeeze. "Watch it," he warned. "You might get me started again." That actually kinda scared me because I was pretty well sated. I didn't know if I could handle another round with him so soon. My thighs were twitching and the flush just wouldn't go away. We both had permagrin. So we kissed for a little bit and he caressed my body and we talked about meaningless shit and then he zonked out. I thought I could just fall asleep but I'm all wired now. He's so smart and considerate and cute mature and great in bed. What more could a girl ask for? I think he's captured my heart like he captured my clit in his teeth. My First Real Man My first two submissions to Literotica were my first attempts at fiction of any kind, not just the erotic. This third submission is not a work of fiction, but the true story of how I lost my virginity to a lovely kind and considerate older man. I promise this prose is 100% genuine. I first met Roy online some months ago; I had a profile on a well known Transvestite Website. I was a little put off at first as I had stated in my profile no admirers, " Girls Only" but there was something special about this man, he was sweet and so patient with me. Roy described himself as mid-sixties fit, tanned, and a lover of "Girls". Could see from his profile he looked nice and he sent me some pictures of himself with other girls. We chatted and got to know each other a little better. Sometime later we agreed to meet; Roy said his wife was working so he would have the house to himself. So our date was set for the following Friday morning, Roy gave me his mobile number with directions to his house, the idea was I would drive to his village and then phone him to get directions to his once. I spent all Thursday afternoon preparing for my first "date" I shaved myself all over, and selected what I was going to wear. The next morning I was so exited and nervous at the same time, I had to see my wife off to work then prepare myself. I started off by showering and pampering myself, then I dressed in matching bra, kickers and suspender belt with black stockings. Over which I dressed in a sweatshirt and jogging bottoms. I then packed a bag with my girl cloths, wig and jewellery, and set off on the journey to Roy's village. All the way there I was so exited, with butterflies in my stomach. I reached Roy's village and phoned him, but got no reply, I phoned about 20 times with no luck. I was so upset I could have cried, I wondered what had gone wrong. Dejected I made my way back home. When I got back in the house I dressed in all the clothes from my bag and spent the morning watching porn and playing with my panty clad hard cock thinking of what might have been. When I did eventually get in touch with Roy, he was so sorry, it turned out he had given me the wrong phone number! We both apologised and promised to meet again, I was just a case of trying to get time together, with one thing and another it took longer than either of us thought. Some time later we managed to arrange a day where we were both able to meet, so we decided to try again. I went through the same routine of shaving all over the day before, the next morning showering and dressing in my sexy lingerie over which I had on a track suit. I packed my bag again and set off. I phoned Roy as soon as I arrived in his village, he answered and we were both so pleased it was finally going to happen. I pulled up outside his door and walked up the garden path trembling. Roy opened the front door and let me in. We exchanged pleasantries, and then he showed me upstairs to where I could change. I quickly removed my tracksuit and dressed in a short skirt and white see-through blouse, I put on my high-heels and my long blonde wig, and I made my way downstairs and walked into the living room, all Roy said was "wow". We sat together on the couch and started to kiss and cuddle. I felt Roy's tongue exploring my mouth and his hand was on my knee. Roy then asked if he could take some photo's of me, I said why not, Roy had me pose sat on the couch sowing a bit of stocking top, he said "Lovely" We then went back to kissing and cuddling, Roy then asked if I wanted to go upstairs I agreed so off to the bedroom we went. I sat on the end of the bed with Roy stood in front of me and I undid his trousers and released his cock, I kissed the end of it lovingly then proceeded to suck the whole thing into my throat, I was in heaven. I sucked this mans cock for some time, the only other cocks I had sucked previous to that moment had always belonged to nylon clad girlies, this was my very first man. Roy then stood back and got undressed, he then joined me on the bed where we laid and kissed and cuddled. Roy began to undress me, I lay on the bed and Roy knelt above my head, I sucked his cock deep into my throat while he played with my nipples. I continued sucking this powerful mans big cock for what seemed an eternity I was so turned on and felt so sexy. Next Roy lay down beside me and we kissed and he held me in his arms. He then moved down my body and pulled my sexy black knickers to one side and slipped my girly cock into his warm mouth. This man certainly knew how to suck a girl's cock I was in heaven. Roy then asked if I was ready to give myself to him I nodded in the affirmative and positioned myself on the end of the bed on all fours. I felt his hands sliding my knickers down and caressing my bottom cheeks. He then knelt on the floor and proceeded to tongue my pussy, I felt his tongue move in and out of my pussy, this was a delightful feeling, then his tongue was replaced by his fingers, first one then two. I was enjoying myself so much I played with my nipples the whole time. Then it happened Roy withdrew his fingers and slipped his cock into me, at first he was very gentle, but once I was comfortable he really let rip and truly reamed me. I was so turned on I looked down between my own legs and could see come dripping out of the end of my cock, which was not even fully hard, I scooped the come of the end of my cock and licked it of my fingers. Roy continued to fuck me, and then I felt him stiffen up and come inside me. He came in 5 or 6 spurts and I felt them all deep inside me. Roy withdrew from me and took his condom off. I collapsed onto the bed totally used, but very happy that I had at long last lost my virginity. Roy lay on the bed next to me and I put my head on his chest, we chatted for a while and while we talked I started to play with his cock which soon started to grow, so I leaned over and started to suck his cock, I alternated between sucking him then wanking him, I was in T-Girl heaven. Once I had gotten him hard again I lay on my back and open my legs, this divine man placed my ankles on his shoulders and slipped his cock into me. I loved being fucked again, he started to ride me hard and I started to wank my cock, we carried on like this until I felt him stiffen and start to come, this pushed me over the edge and I came at the same time, my girly cock sprayed come all over my chest and I felt my orgasm from deep inside me. I lay back totally exhausted but happy in the knowledge I was no longer a T-Girl virgin, and had just been fucked twice by a very sexy man who had used me as his slut and I had loved every minute of it. I have spoken to Roy since that day but we have not managed to repeat it yet, we will tho and when we do I will add chapter two. My First Real Massage True story. I swear. I had been to a few massage places. They had been enjoyable but nothing really cfnm, until this one lady I called. I saw her add in the Reader. She sounded real nice on the phone. She was energetic and had a Boston accent. I made an appointment. She ran this service out of her house. When she answered her door I was pleasantly surprised. She was in her late 40’s but still really put together. She had on tight fitting shorts and a tight tank top. She seemed really please to see me too. She smiled, looked me up and down, then said in her Bostonian accent, ‘Ohh my, your real tall!‘ I’m only 6’ 3’’ but still I don’t mind complements, even if it’s bs. She showed me to the table. Smiling she said, ’Please take off ALL of your clothes...or whatever you feel comfortable with. You can hang them up over there. Then lie face down on the table with the towel over you. I’ll be back in a couple minutes’. As she moved toward the door I removed my shirt. With my hands on my belt buckle I saw her sneak one last peek before closing the door. Our eyes made contact and she seemed really embarrassed and she looked away and closed the door. I stripped off. Now down to only my boxers, I remember what she had said. ’Please take off ALL of your clothes’. I fondly remembered how she stressed the word ’ALL’ and how her eyes lowered a bit when she said it. Well I thought, don’t chicken out now, you might never get this opportunity again. Down they went.. I stood there for a second or two enjoying the weird sensation of being naked. I got on the table, on my stomach. The soft table felt exquisite to my cock, which soon became erect. I pulled the towel over me. It wasn’t a very large towel. It covered my buttocks and the sides but that was about it. Also it was a thin white towel. I wondered if it would be practically see through when I turned over. It might not be see through, I thought, but it certainly wouldn’t offer much protection from her gaze if she chose to look. But that didn’t bother me, in fact, I hoped she did look. I wanted her to look. That’s why I was here. That was my fantasy, that some legitimate masseuse would become so enthralled with me that she couldn’t keep her hands off me. There was a knock on the door and she came back in the room. As she was doing the massage we made small talk the whole time, you know TV, travel, sports, the weather etc. She was really good too, you could tell that she had training. As her hands worked my back, waved of pleasure shot through me. The feeling is indescribable as you get those chills down you spine. But anyway when she started on my legs, she really creeped up the inner thigh. Then she made long strokes up and down my leg. Each stroke got longer until her hands made forays to my cheeks. Her warm soft hands went under the towel, but each time she did so she pushed the towel farther off of me. She had moved the towel around so much she had to see my balls. Her hand came about as close as you can come to touching them. The conversation had died out at this point, we were both really concentrating on what was happening. She worked the buttocks too. (no anal shit mind you, that is where I draw the line). But this was great, definitely worth the price of admission, the previous masseuses didn’t do this. She spent alot of time here. Her left on kneading my left cheek , hip and side of my thigh, as her right hand worked the center of my thigh, then the inner thigh. Then she moved the towel back to it’s starting place fully covering me. Then she worked on the other leg, repeating the delightful process. Although this time her stroke moved the towel almost completely off of me. The combination of the physical sensations along with the other aspects of the situation were intoxicating. The feel of her warm hands masterfully working my naked legs and butt. The thought that I was almost totally naked before this strange lady. I wondered. What was she thinking? Was this par for course? Just a job? Boring for her? She had to be able to see my balls. Did she look at them? What did she think of them? Did they hold her interest, or was it like seem one you seen them all? Then she picked up the towel and then she asked me to turn over. I was looking at her when I did, so I could see her expression. She seemed to be looking away, but kind of looking out of the corner of her eye. As she put the towel back down on me, I exclaimed to her that felt GREAT. And it was the best massage I‘ve ever had, etc. She smiled and said thank you. This led to some more small talk and what not as she started working on my arm and hand. We talked about vacations, the coolest places we’ve been to, places we would like to go, our favorite music, foods, movies, etc. This was a really great experience the massage was great, even the conversation too. And this lady was not hot but she was attractive. She said I was so much nicer to work on then her other clients. She said she usually had rude old men. (I’m in my late 20’s and work out alot, I’m not a GQ super model but I’m not bad.) Need less to say when she was rubbing my stomach I couldn’t help but start to get hard. She seemed to be looking at it beginning to grow. Her hands were rubbing so close. I felt the cloth rub my cock as my cock expanded. This towel did little to conceal it. She could clear see the outline of everything. There is no way that she could not see my erection. This towel barely covered me. The bottom just covered my testicles while up top if my dick had been a half inch larger it would have protrude out of the top of the towel. As her hands traced little circles on my lower stomach along the edge of the towel, she smiled and seemed to purse her lips almost as if she was saying, ‘ooohh’. She finally realized I was watching her intently. She a little bit embarrassed, as she sheepishly smiled at me then broke eye contact. It seemed to say oops, I was zoning out a little bit there and you caught me. She grabbed the side of the towel and gently flipped it over to expose my upper thigh. As she did so the folded over part of the towel lightly landed on the area of towel that my cock was under. That light contact felt electrifying. She never touched my genitals, but she seemed to have ways of moving the towel around (during the course of a normal massage session) that would make the contact for her. She did the front side of my leg. Then she went to do the other. She grabbed this side of the towel and folded it over. Now I was completely naked except for this little towel, neatly folder over my erection. Her hands made long strokes over my legs, and stomach and around to the other leg and back again. She seemed to be waiting for me. I really wanted to ask her for a ‘favor’. ( I had never done that before so I was really nervous) but I chickened out. Finally with one hand on my thigh and the other on my stomach she said, ‘How do you feel, are you relaxed?’ I replied yes. Then the a little pause. Then she finally said, ‘take you time getting up’. And so ended the massage. After I paid her I asked her if I could set up another massage. When she came back with her calendar book she stood really close to me, within my personal space. I could smell her perfume and her being this close gave me a great view of her cleavage. My mind was swimming in possibilities. The next week, I’m back there again. We again made small talk as she let me into her house. The weird thing was that she followed me back into the room, still making the small talk. So I was like okay, and I took my shirt off. She’s still there leaning up against the wall. So next my shoes and I sit down to take off my socks. She is still there and we’re small talking. I’m thinking that this is really exciting. Her is this lady looking at me who other then small talk I really don’t know and I’m about to get naked. I stand up and pull down my shorts so I’m down to my boxers. She is still there!! She isn’t ogling but she is sneakin peeks here and there. I must admit I wussed out her. I stood there like a moron for about 3-5 minutes continuing the small talk in my boxers. Then she seemed to get the idea that I was nervous about this and she left the room. (mind you I’m not ashamed of my body, I’m in good physical shape and I sport 6.5 ‘’ when erect, but this was just weird, I hadn’t ever done anything like this. Ya I had gotten laid before but that was a totally different context. That was kissing and hugging getting warmed up etc. And it was always their clothes coming off first anyways. This was weird being so unclothed in the presence of a clothed women.) But anyway, she left and I pulled off my boxers and got on the table, on my stomach. Pulling the towel over myself I was thinking why did she stay? Was she really enjoying the view? Or did she do that with all the customers? When she came back in the massage proceeded like last time. Except this time I could have swore that when she was rubbing my inner thigh one of her fingers very lightly made contact with my balls. I figured I was imagining it. Then she asked me to turn over. She put the towel on me and started on my thigh. But she seemed confused and kept on fussing with the towel. I asked her if everything was okay. She said that she normally did not use a towel. And I summoned up the courage to say something like ‘Er ah we don’t need the towel’. Her eyes sparkled as she removed the towel. This feeling of being naked in front of a woman in this context was incredible! Better then coke, whiskey, acid, weed or anything! It felt as if her eyes were invisible hands that were massaging my cock! She continued the massage as before, totally ‘professional’ , except for I was completely naked before this women. And she was working my thigh and hip. She was looking right at my Johnson. Even though I was excited, I was scared so I was limp. We continued the small talk. Although the small talk had definitely changed at this point. We were talking about nudism. She said that a body was just a body etc. Not a big deal. (Then why was she totally looking me over? Was it my imagination? Maybe she was a nudist and this was just a normal massage?) But anyway, I was buck-naked and this fully clothed lady was rubbing oil onto my body. Later on she started working on my stomach. The small talk seemed to die out. She was doing circular strokes on my stomach and occasionally running a hand down the length of my leg, then back up again going up the inner thy back to my stomach then my lower stomach. This whole time she is now blatantly staring at my cock.. I had been only sneaking peeks at her this whole time but now I’m getting a little bolder. I’m looking at her and her eyes are fixed on cock almost willing it to get hard. I look at her tits and they are big. Almost too big for her skinny frame. Then it started to happen. My cock started getting hard. As it was uncoiling I looked up from her tits and at her face, was that a smile on her lips? Yes, that was, she is definitely enjoying this also. Here I am totally naked in front of this clothed lady and my cock is growing into a full erection. She is rubbing everything except my cock and balls. But she is so close to touching it. This went on for a blissful minute or two. Then she picked up the towel and put it back on me and said that was it. My mind was swimming. Was this lady a cop? Was I going to end up humiliated on public TV or the local paper? To hell with it I didn’t care. I asked her something to the extent of would she er um er and I put my hand on my cock through the towel and kind of rubbed it through it a little bit. She seemed to be thinking the same thing adding it up. Was I a cop? Would she lose her license? I would like to think that this was the exception rather then the norm for her ‘business’ and I was a lucky exception. Then she said ‘Okay sure!’ and with that the towel came back off and she applied some oil to my balls and went to work on them. For at least 5 minutes she rolled my balls in her hand. She dedicated herself to them, but she never touched my cock. That was until with one hand she grabbed my sack and pulled down on it. This forced my raging hard on to point straight in the air. With her eyes dancing from my cock to my face and back to my cock again she said, ‘I can’t believe I am doing this, I never do this’. I thought Ya dee ya dee ya da Was this some more ‘ooh your so tall crap’? But I didn’t care really. She let go of my balls and my cock slapped my stomach with a thud. She then grabbed the bottle of hot oil and starting at the base of my penis poured a trail of oil. She continued up the shaft to the head. Her hands felt wonderful when they made contact. She knew every trick in the book. I was in heaven. Finally, she settled on brining me off. Her left hand firmly grasped my shaft and the other tickled my balls. This lady fully clothed was now stroking my cock.. I put my arm around her, holding her close. I looked down at her hands working me then up at her face then I blew a load that would have put Peter North to shame. It went everywhere. I had been saving up this load for 8 days. The best part about it was that this lady was delighted, and squealed at the first squirt and then met each successive squirt with a ‘ooh’ ‘my’ ‘ewe’ ‘oh’ ‘ya’ With determination she squeezed out the final oozing of cum. She said she hadn’t seen that much cum in a long time. Inwardly I cried ‘YES!!’. She did a good job of cleaning me up. I’ve had about 80 massages (from mostly different masseuse), but I’ve never been able to repeat that. I’ve had lots of good experiences since then, but I guess there is something special about the first time. ---------------------------------- This story is a true story. It is lame though because it is told from my point of view. A man’s point of view. I’m not an author I can’t write in the 3rd or 2nd person or whatever it is. So I just did a brain dump of what I remember. What I would really like to know is our there any lady masseuse out there that have had similar experiences. I would love to hear those stories from your point of view.