Getting my first penis on the way out of town
written by:
lucy

After a few years of marriage, my husband asked me how I lost my virginity. I was very hesitant to tell him since it made me look like a total slut, but I did. It was a calculated risk. I knew he was a kinky guy and it might turn him on. Lucky for me it did, and he helped me write the story. I was sort of a tomboy, and most of the descriptive phrases used are mine. I didn't have to embellish much! So here is my story...

I was a virgin until I was 25. That was 10 years ago. My sex life started with the kinkiest night of sex I have ever had. I did it all on the first try. It wasn't a romantic, loving experience. It was the kind of experience every woman dreams about from time to time and wishes they could have when they are in touch with their really naughty side. I was lucky to have had mine and not spend the rest of my life dreaming about it, wondering what it would have been like to have two studs do me like this.

I was one of the first girls in my class to have breasts. I started masturbating when I was 12. I had a very insatiable and wet pussy, and a very vivid imagination, all contributing to create a young teenager very eager to explore her sexuality. I had two older brothers, which helped me learn about sex quite a bit from a guy's perspective, and it gave me access to a lot of porn. As an adult, I probably watched more porn than most men. If I didn't have a date, which was pretty much all the time, I was masturbating to porn. I am 100% sure nobody would have guessed this about me, since I was the shy nerd who was active in the church and dressed very conservatively.

And yet I never had sex, I just imagined it. The reasons were complex. I was religious, and wanted to have sex with the man I married, or at least would marry. I had not even been in a serious relationship and been tempted much. I went to a conservative, small college. I had a nice figure but did not dress well or make myself up well. The few times I met a nice guy who made me want to have sex, I did not get approached. Or I went on a date and it didn't work out. I would spend the night on my stomach in a dorm room quietly rubbing my clit until climax, trying not to be discovered by a sleeping roommate that I did not know well.

It was about a week before I was to leave North Carolina. I had given up on my job here since the economy was rough and I was really going nowhere. I was in I/T, and my plan was to return to Iowa and get a job closer to my family. My aunt and uncle had moved away from NC, and I didn't have many girlfriends here. I wanted to be married by now, and I wasn't meeting many men here either. Personally and professionally, my life was going nowhere.

I had finished packing up a lot of stuff, and I was sweaty and preparing to take a shower. I looked in the mirror and admired myself as I took the spandex and sports bra off I had been wearing to the gym before packing. I had a tall frame at about 5'10". This is not exactly petite. I was slightly big-boned, but not overweight. I have a slim waist and large, C-cup breasts. I have black hair and full lips that I was very proud of. I thought I was awesome naked. But in the office with all the women who dressed well and had the best hair, I felt like a plane Jane. But if only all the men could see me naked, that would be the great equalizer. I worked right down the hall from all the young, skinny sluts from accounting, and they were a tough act to follow! I did feel great about my body, though. Plus I had trimmed down a little over the past six months, and I knew men were seeing me a little differently. I got looks from guys now, which did not happen as much before. I liked them. It wasn't just because I was naturally so horny. It was because I was unspoiled. Unlike those blonde, petite Barbie dolls that had men dying to fuck them since junior high, I did not get so much attention. I was humble and never took it for granted when I could tell a man looked at me and I got the vibe that he wanted to fuck me. I thrived on the attention.

Oh I forgot the most important detail about my appearance. I am black. This of course changes everything. Would you expect a black woman that looked good to be a virgin at 25? I felt like an alien on my own planet. I grew up in small town Iowa, where there was a very small group of black people at all. We didn't speak Ebonics. We blended in. My friends were white. I went on dates with white guys. If you didn't like the one or two black guys your age at school, you had no options. I came to Raleigh and was so disappointed. Black men as a whole were so frustratingly irresponsible and immature. All the women were overweight and had little in common with me other than skin color. Even though in my opinion I had the best black ass in town, the men seemed to go for the fat girls instead! Argghh! I shied away from the social events where all black people self-segregated and hung out, and instead hung out on my own or at the church which did not have many blacks. Plus now I experienced some bad attitudes from people, black and white, due to race. This was so appalling. I never had issues like that in Iowa where there were only a few of us, but we were more truly integrated. Because of that, I had absolutely no chip on my shoulder, unlike all my "sisters" from the south.

This all contributed to me not dating much. Plus I wasn't attracted much to the white kids to be honest, and they were totally intimidated by me anyway as the tall, black lady. And that is how I still had a cherry at my age when most of my peers had already had children.

I continued to admire myself in the mirror. Over the years I had developed some insecurities about my body like any woman, but overall I was pleased, and at this point in time I was more pleased than ever. I had the full, beautiful lips typical of women that looked like me. While not a beauty queen, I was happy with my cheekbones and the overall appearance of my face, and I had brushed my teeth growing up and had a good smile. I really liked my breasts. They were C cups, but I could probably get away with wearing a D-cup bra. They were very firm and shaped very well. I liked my dark complexion and the way it looked with the even darker circle in the middle with the different texture of the large areolas. My nipples were good sized but not obnoxiously huge. They were very sensitive also, and when I stimulated them as well as my pussy I always got off better and faster. I turned quickly, and I saw them jiggle nicely. Now I looked at my ass. After working out hard to get back to my high school body fat levels, I was left with a stronger, firmer ass that even those times. I definitely had some junk in the trunk though. My African genes had left me with plenty of booty for people to look at. If you are a guy favoring the typical Chinese girl with a flat chest and extremely narrow hips, then I was not the gal for you. But if you liked a girl who was fit but still had some serious curves, I would do just fine. I turned to admire my front.

I had rather large labia and a pronounced clitoris. I could see them well because I kept my pussy shaved bare. I tried shaving once and thought my pussy was so pretty, and the hair so ugly, that I kept it this way even though nobody but me saw it. My lips were large enough to hang down and look very cool from behind with my legs spread. I began to run my fingers between the lips, up and down, spreading them apart and playing with them. I liked the dark lips and the light pink flesh between them when I pulled them apart. I couldn't really see the hole since I was standing, but I could see the clit, and I rubbed it between my fingertips. I ended up on the bed to get myself off before taking a shower. This time I was thinking about a white guy in my church group named Ken. He was tall and well-built, with a great personality, and an exception to the rule about white men. If only he would notice me. Oh yeah, and leave that attention-hogging bitch he was with. Ken and I were pretty close as friends since we worked out at the same gym and he was sort of my unofficial trainer. I had a rock hard ass, and he was partly to thank for it. Too bad he wasn't here now to enjoy it. He was a white guy though, and I just knew it wasn't really practical anyway as a long-term match. While my body craved him for short-term attention, I knew I would restrict myself to long-term compatibility for any sexual relations. It was too bad. I wanted to try a white guy once in my life.

I did owe Ken a lot. He offered me his services for free and off the record, and I think he had a sense of pride in the hot body he had created. I always liked it when he put his hands on me to show me a certain exercise correctly, and I did sense his hands stayed on me a little longer than they needed to. I had masturbated often to a certain fantasy I had where we stayed past closing, and he fucked me on one of the weight lifting benches in various positions, all sweaty from our workout.

After a few minutes of expertly rubbing my clit, I slipped a finger inside my very wet pussy. The finger went in easy after years of practice. I was still a virgin, but was unsure if I had any hymen left. I had even put two fingers in a few times and felt the tension of my tight pussy. I imagined a large cock entering me. It was almost too much. I felt a deep longing that only a cock could satisfy. Soon I would be starting over in Iowa, and who knows how long it would be before I could feel the real thing inside me. I felt a sudden sadness and sense of urgency, worried that I would never get to put this great body to use.

The next night I went to my farewell dinner gathering with my church singles group. Ken and Randy were roommates here, about my age, and part of my church group. There were 10 of us, both guys and girls. I was feeling very good that these guys put this on for me, although I wasn't particularly close to any of them. And I kept things in perspective. Everyone who left the city got a farewell like this. Randy was perpetually single and had a reputation for being a bit of a player. They made quite a pair as roommates. I had fantasized about fucking them both. The cool thing was there were rumors that two different women were involved with a threesome here. These women were not in our church group of course, so we weren't sure what was true. We knew for a fact one other girl had dated Ken first then switched to Randy for a while. I had also fantasized about being one of those girls before! Randy was a sharp looking fellow also. Too bad that would never happen. I wanted to remain a virgin until I was married, but a girl could dream, and this was quite a dream.

I enjoyed my dinner, but I kind of felt like I was being teased, leaving town and having to say goodbye to these guys. Things picked up a bit because Ken's bitch girlfriend was not there, and when one of the other girls inquired about this, he told us they had broken up a few weeks ago and just not told anyone. My heart leapt. Not that I would be with him anyway, since here I was leaving just before possibly something could have happened. I didn't know Randy's status, but I imagined he was single also, keeping his options open. Ken's stud roommate was equally as hot, but he kind of made me nervous. He was very nice and always talked to me and smiled, being very confident. He had a lot of sex appeal, and had a reputation as sort of a player, having supposedly slept with a few of the hottest girls at church in addition to the stories I mentioned earlier.

There was one black guy there named Theo, but we didn't really click. He looked good and all and was single, but he never made a move as long as I had known him. We did talk a lot, and I think maybe he cock-blocked the white men just by being in my church group. Maybe he was intimidated. He was a couple inches shorter than me. That wasn't a show-stopper for me, but guys were just as weird about that sort of thing.

This was a church group, so the conversation stayed pretty tame, and only a few of us were drinking. But it went on for a few hours since we watched a movie, and by the end I had drunk a few drinks and I was feeling pretty tipsy. I had been horny all night thanks to the masturbation session I had conducted the night before coupled with the presence of two men I was dying to fuck. People starting leaving, and soon it was just me and the two boys. Even Theo left without much fanfare. This was perfect. I was not great friends with the women, and I was not interested in the other men. They were nice fellows, but also less attractive and much more conservative. I felt it appropriate that I helped clean. I guess I also fantasized about them putting the moves on me and giving me a turn for a threesome. But I would have to decline anyway to keep my virtue, but maybe it would make me feel good just for them to try. It definitely was one of those fantasies I would wish would happen, but would never actually come true. Like I said earlier, I did want to try a white guy in my head. Too bad I wanted to marry a black guy, and marry as a virgin. Oh well. These white guys probably had smaller penises too, and that might have been easier for my first time. As we finished, Randy said, "Lucy, why don't we sit down for a bit and have another drink, then one of us will take you home. Tell us about your plans."

Ken and Randy sat on opposite sides of me on the couch and engaged me in conversation. I was able to carry a good conversation since I was a little drunk, and I quite frankly enjoyed the attention. They began to ask me personal questions and ask me about why I had remained single. They told me they were very attracted to me and began to specify parts of my body. They said just enough romantic stuff about my eyes and other parts of my body to keep it from being too childish and perverted. They jokingly asked me to stay and not move to Iowa.

"Enough! I said finally. I was enjoying the banter now. "I haven't seen a man naked since I have been here. It's time to see if men in Iowa want this." I stood up dramatically, and the men stood up to protest.

When Randy said he had always wanted to kiss me, it was too much. I leaned in and initiated a kiss! I t was a huge step for me, and it was exactly what they both wanted it turned out. He was very good, and soon our tongues were intertwined. I broke it off to see Ken smiling at us. I was worried it would be awkward since I can only kiss one guy. He smiled and rubbed my back. "Continue" he said. So I did.

Soon though Ken had seen enough and wanted to assert himself as a participant, not a spectator. "Stop hogging her," Ken said and pulled me away. He cupped my face and leaned in and kissed me too. This was really weird, but I was going with the flow, since this was the most action I had had in ages. As Ken kissed me, and he was also an awesome kisser, Randy rubbed my back. I barely noticed he was under my shirt until my large breasts suddenly felt the resistance of my bra disappear as the strap was expertly undone and they hung naturally.

"Oh wow. I don't know," I waffled, the nervous virgin in me protesting. This was actually happening. The rumors about them were true. I had to turn them away, even though I would regret it forever and always wonder what it would be like to have these guys fucking me.

"Let us give you a great send-off and make up for all the neglect you have suffered in North Carolina," Ken said.

"I've never kissed two different guys in a week, let alone at the same time," I confessed, trying to justify my protest. The look on my face was of concern but excitement, and while my look might have suggested I don't want to do this, it really said "I want you to talk me into it."

"You deserve the best attention tonight. We want to please you and make you happy."

Ken began to kiss me again, and Randy moved behind me, and I felt him cup my breasts. He rested there a minute feeling their fullness, and then tickled the nipples. Soon he pinched them a little more firmly, which is just the kind of pressure I needed at that exact moment. He was very good. It felt awesome, and the stimulation he was providing me caused me to kiss Ken more passionately. Randy moved one of his hands to my front, and the button to my jeans was undone and the zipper moved down halfway. I barely felt the tug on my clothing, Randy was so fluid and adept at removing a woman's clothes! Ken stopped kissing me and looked into my eyes and smiled, reassuring me as Randy pulled my pants down. I felt cold and exposed. Goosebumps flared out across my body. Ken smiled and slowly pulled my shirt and bra off over my head and stood back to admire. "Wow, girl. I had no idea. Your breasts are perfect." I loved the admiration. I felt the same way about my tits and was very proud. I was a bit of an exhibitionist at heart, and this was a huge turn on. I guarantee I was the only virgin on the topless deck of the cruise I went on with my parents when I was 18, when they weren't around of course!

"You should see her tushie," Randy said. "Didn't you say you worked out with her? You should be very proud!" He had a great view of my ass, because I was wearing a sexy black thong. I had no idea it would be needed tonight, but it made me feel sexy to have it. I liked to feel sexy even if I wasn't getting any. The sexy undergarment was in stark contrast to the drab shirt and loose jeans I was wearing over it.

Ken leaned down and kissed my right nipple while Randy kissed my ass. I stared off in the distance, scared to death, but not wanting to miss the hottest moment of my life thus far. It helped that this was my last week here, and I would not have to see these guys in church the next day. These were the perfect circumstances, the only circumstances, where I would have allowed this to happen. We were all single and attracted to each other, and I was about to leave and start a new life.

Randy eased off my thong, and I held my breath in anticipation. No man had taken off my panties before, and I was worried and insecure for a moment. I shaved myself bare, and was not sure what they would think.

"You have a beautiful pussy," Randy said. "I like big lips and a close shave." This made me feel relieved. Those of us with large labia are always self-conscious, so it's good to know the guy you are with has that taste.

I laid back on the couch with their encouragement. Randy disappeared and Ken sat next to me, continuing to kiss me and fondle my breasts. A few minutes later, Randy returned, stark naked. "Oh my god," I said. He was ripped and had beautiful abs. His penis was limp, but still obviously quite large. He was uncircumcised, which I thought was odd. I had never seen that before. Truth be told, I had only seen a few cocks in real life before, and only touched one when I got drunk at a party in college and performed my one and only blow job. That penis, while black, was definitely smaller. This man was larger than my brothers I had seen. My hunch turned out to be correct. Over the years after this I saw many penises, and the only one larger than this I would come across was Ken's.

Randy knelt between my spread legs and rubbed my thighs, waiting for now before attempting to touch my most private places. "Wow. You're very horny for us already I can tell. That is one wet pussy," Randy said, as he could see the lips glisten with moisture. Ken lifted my legs up and back into a very obscene position, allowing Randy see my exposed pussy and asshole.

I felt unsure about how far I should let this go, and I pulled Ken's hands off my legs, but I only partially closed my legs, still leaving Randy access. "Oh my god, I can't believe this is happening." I paused. "Listen guys, I don't know if I should do this. You are not even my boyfriend. Boyfriends. Whatever."

Randy said, "We know it's what you really want. We'll go really slow and do things when you're ready." Nice. It sounded good, but what that meant to me was, "We're still going to fuck you, just let us keep manipulating you until you beg for it."

It felt so good to have these two studs admiring me. In an odd sort of way, having two of them instead of one made this easier. Who would have thought a threesome was easier for my first time than a good one-on-one lovemaking. There was no pressure since I was leaving tomorrow. Having two people on me gave me a sense of security since there were more witnesses to keep each other honest. I felt safe. I don't know. This all just seemed too easy.

Randy kissed around my waiting vagina for a while as Ken continued to look at my eyes reassuringly as he fondled my nipples. After he knew he had me dying for what was going to happen next, he kissed me right on the clitoral hood, then gave it a gentle suck. The feeling was something I had never felt before. I practically came on the spot. It was so much better than my finger. I looked dreamily back at Ken. "Get naked," I told him, for lack of a better expression. Ken did just that, and I was rewarded with a stud with just as good a body as Randy. He was slightly taller, and his penis was downright enormous. I took my focus off him as I felt Randy begin to perform excellent oral sex on me for the first time in my life.

"Mmmm," I said contently as I ran my hands through Randy's hair. I was nearing orgasm already, and my breathing quickened. I turned my attention back to Ken. His erection was growing now and he had a good semi-hard cock. It was very attractive and perfectly shaped and large. Ken shaved also, and had no hair on his cock and balls. I decided I liked this aesthetic look. Randy shaved also and had just his patch above his penis. I reached out tentatively and grabbed the glorious cock in my hand and gently stroked it up and down.

Ken got up on his knees on the couch and moved closer so his penis was at the same level as my mouth. He didn't need to say anything; I knew what I saw supposed to do. It wasn't the first time a penis was in my mouth. I had given one blow job before at a party. The penis was much smaller, and apparently I gave great head because he came in about two minutes. I took his load, and I liked it.

So I had no fear when Ken's tool approached. I let the tip slide between my full lips, and I opened wide as the shaft slid inside my mouth. His cock felt huge in my mouth compared to the cock I had sucked a few years ago. My jaw opened wide painfully as I tried to keep my teeth off his penis. I cupped his full testicles as I got to know his penis more, and I could tell from Ken's comments that I was good. Meanwhile, Randy continued to warm up my hole. I felt him slide a finger inside me as I continued to lubricate and move towards orgasm. I could tell how wet and loose I was becoming, and wondered if they knew that I was a virgin. I decided not to tell them. I am not sure why. I think it is because I didn't want to change anything, since I was beginning to think this was happening just like I wanted. I was not being treated like a little girl. They were respecting me like someone who knew what she was doing as they seduced me, and I liked it. I must have had them fooled. I think the shaved pussy lended well to the lie, since probably most virgins don't shave it bare. Randy was clearly just as interested in prepping my hole as he was in getting me off, as he removed his tongue and watched his second finger ease into my vagina. I could feel my pussy stretch to its largest penetration to date, and it hurt a little, I put my hand down and stopped him. "Gently," I told him. "It's been a while for me."

"I have just the thing for you," Randy said and produced a bottle of lube that he had brought in with the towel. He worked it on his fingers. It felt cold at first, but then as his fingers slid inside my tight, virgin pussy, I could tell the lube was helping, and I began to suck cock again. He worked his fingers in and out and twisting them, pressing them at various angles to the sides of my unused tunnel, preparing it to receive a cock. Randy was thinking to himself that I had a tight pussy, but he could tell it was large and deep, probably due to my above average height. Randy then held his fingers steady inside me, two fingers pressing up against the upper wall of my vagina. He focused on his fabulous licking of my labia and clit. He moved his other hand to my vulva, and he pulled back the hood to my clitoris and licked the sensitive button directly. He did this for about 10 seconds, then I went over the edge. I pulled Ken out of my mouth and cried out in passion as my body convulsed with the pleasure. It was amazing, and so much better then my self-administered orgasms of the past.

Ken was playing with my nipples and gazing over my body as I recovered from my orgasm. My heart was racing and I know my face was flushed. I was beginning to sweat. I could feel him looking at the various parts of my body. I enjoyed knowing that he wanted to fuck me. It gave me an odd satisfaction. I am sure Randy was feeling the same way as he gave my over-stimulated pussy a brief break. "I really like your pussy, Lucy, if you don't mind me saying so," Randy told me as he rubbed my thighs, still positioned off the couch looking up at me between my legs. He could barely see my face thanks to the large breasts perched in his view.

Ken took his eyes off what was between my legs and looked into my eyes and smiled. "Do you think you might want to take the next step with us," he said seductively, with just the right balance of hope and nonchalance, making me feel like I was calling the shots when really he was in total control.

"Maybe," I said and smiled, then paused before continuing. "You guys are great at this. How many women have fallen into this trap?" I said jokingly.

Randy answered. "I'm sworn to secrecy, but I promise you're our favorite." He gave my clit a kiss, sending a now-familiar jolt through my body.

My heart was about to explode. I was so excited. This was finally it! I wanted sex so bad. I was done waiting. I was good looking, a nice girl, and a hard worker. I would get that awesome husband one day with or without my virginity. Tonight I was going to take advantage of this great opportunity. I was finally going to have sex.

Randy came up and stood to my right side by the couch. Ken stood to my left. Both had fully erect cocks. I reached out and grabbed them both. I stroked them both up and down slowly for a couple minutes admiring them. Ken's was about the same length and circumcised. It was definitely thicker, although I knew for a fact Randy's was well above average. A little pre-come oozed out of Ken's cock as I milked it slowly. I leaned in and licked off the drop with the tip of my tongue. I looked closer at Randy's cock. It was magnificent also in different ways. It was very big and hard also. I found the tip was completely visible now that he was fully erect and had pushed through the foreskin. Oddly, both men were shaved. I had only seen this in a few porn movies I had seen. I liked the look very much. It seemed very clean, and made the cocks stand out as the center of attention without any distractions.

"Ready?" Ken asked with a grin. I smiled and looked into each of their eyes before answering. They were both so good looking. Each was handsome and over six feet tall and very athletic. I would have been happy fucking either of them tonight. To them it might not be a big deal who fucks me now, but to me, as a virgin, it was a huge deal. I was closer to Ken, had masturbated thinking about him more times, and we seemed to connect better. I just wasn't sure about taking such a large penis into my body for the first time. But I decided I was up for the challenge, even if it hurt a little.

"I think," I said slowly, as if I had given this tons of thought, "I want to try this one first." I gave Ken's cock a gentle squeeze and looked at him so he'd know he'd been chosen. "If you go slowly, since I've never had one this big," I added nervously. I could tell he appreciated my concern, which was really a compliment to him. I turns out both of these would be the biggest cocks to enter my life for a long time.

"I thought they made these in black all the time," he joked.

"Well the biggest one I have seen is white, and it's about to be inside me," I said and smiled.

"We're going to stretch you out on the floor to get started," Randy said. They each took my hand and helped me off the couch, where I had been for the past 20 minutes enjoying myself. I didn't notice, but they already had placed the towel on the floor, on top of their very comfortable, thick carpet. I tentatively laid down with my butt on the large bath towel, and Randy appeared with a large, comfortable pillow, which he placed behind my head. Ken helped ease a smaller decorative pillow under my butt. It was a very comfortable position actually, and there was plenty of room around me for the men to work. They had obviously given this some thought. Excellent. I liked confident men that were good planners!

Randy laid next to me propped up on an elbow, with his head near mine. He had one hand on his penis, and the other one went around my head and played with my right breast. He leaned in and kissed me deeply.

Ken had positioned himself between my legs. I subconsciously spread my legs to make more room for him. Ken had not really seen my vagina up close, and he didn't stop to do it now. He was looking me in the eyes and smiling reassuringly as he got into position. The pillow underneath me raised me up to the perfect height, and I could see his magnificent cock standing up straight, hiding his belly button. I saw the bottle of lube next to my head on the right. I opened the top and put some of the slipper stuff on my fingers. I reached between my legs and gently grasped Ken's penis, rubbing the liquid on the head and first few inches of his shaft. I stroked him up and down a few times. Randy put his hand down to my crotch and put his middle finger inside. "You're so wet and ready, girl. Go ahead, put it in your pussy," He pulled his finger out then used it with his thumb to spread my prominent labia and push them to the side, out of the way.

I brought Ken's cock downward. He pulled his hips back to give me room, and the large head pressed firmly against my labia. First it struck my clit near the top, and then I pushed him downward and felt the tip slip inside my wet cunt. There was no mistaking what was going on. Part of his penis was inside me now.

Slowly and gently he eased forward. He was still looking me in the eyes, which I thought was very tender and erotic. "Lucy," he said, "I think you are stunningly beautiful. I knew since the first day I met you that you were hiding a wonderful body from us. I've always wondered what it would be like to fuck you. I've wanted this for a long time, and there's nowhere I'd rather be than inside you right now."

"I've wanted you like crazy, too," I said.

He continued forward, and I felt a blunt pressure building up inside me. I also could feel the tension in my vulva area as the skin and tissue all around my hole was stretched and pushed to the side. More and more of my pussy started sending me a mixture of pleasure and pain as he penetrated and made contact with more parts of the vagina, deeper and deeper inside.

"Oh my God," I said.

I wasn't sure if it would hurt, but it did. I thought I didn't have a hymen anymore, but there's no doubt when he pressed forward a little more, he popped my cherry. I felt it change from a firm feeling of stubborn pressure to a sharp pain. Ken seemed puzzled by the brief resistance, but I think he thought I was just tight from not having cock in so long, or perhaps still a little dry on the inside. He didn't pause much, and he continued inside me. I could tell he had pushed past my cherry. The pain was starting to subside, but the dull ache from my entire walls stretching more than they had ever done before was still getting worse as he probed deeper. "Ahhhggh," I said, which I tried to make sound like pleasure and lust and omit the small groan of pain mixed in. I put my hand on his hip reflexively and exhaled deeply, holding him from going further. After a few breaths I decided to get it over with, so I let go, and Ken continued. He was still tender and slow, and it took him about 15 seconds to fully penetrate me. I felt his hips meet mine, and I could feel his balls on my butt cheeks. I couldn't believe that whole cock was inside me. I was so proud of myself.

"Mmmm. That feels great, baby," Ken said. He slowly began to pull out his large cock. It felt like his penis damaged my inexperienced vagina on the way out too, as the tight folds of flesh inside protested to the friction and stretching the other way. Ken pulled out just far enough to where only the head remained inside, and I could see the shaft back up from between my legs. He then drove forward back into me and began a steady tempo of penetration. I closed my eyes dreamily and gripped his forearms. He was propped up supporting most of his own weight as he stroked me. I opened my eyes and saw Randy looking at me and smiling as he pinched my nipple again. I imagined that he wished he was the one fucking me right now.

Ken probed in and out, over and over. He was driving his cock in with full thrusts, deep into the back of my pussy. I felt his balls flatten against me at the end of each deliberate cock-stab. I was quite tight, and Ken was sweating with exertion. He was still taking his time, and the penetrations were coming at slow intervals, which my newly deflowered pussy thanked him for.

After about five minutes of this, the pain inside my torn hole was mostly gone, as my vagina was sufficiently opened. Ken's enormous cock was rubbing my clit perfectly, and the stimulation along all the rich nerve endings inside my pussy was driving me crazy, building me up to another orgasm. As I would later learn from experience, this man had a very big cock, and it did things for me other men could not. It accessed the deepest part of the pussy and brought me more pleasure there, while the walls of my pussy were stretched and rubbed better as his impressive girth filled me up.

Ken began to pound into me harder and harder. My breasts started bouncing up and down in a hypnotic rhythm. I welcomed the escalation, because now I was ready for it. Ken expertly had put me on the floor instead of a bed, and this allowed him to get faster and more firm penetration since there was no give in the floor, and we wasted no energy as his cock worked its magic on me.

"Wow, my Lucilda. You have an awesome pussy. I can't believe how tight it feels; I never would have guessed. Especially since you can take me so deep. It's such a joy to be able to stuff my entire cock into you."

I thought now was the best time to tell him. "Well, that's because I am a virgin. Well, I suppose I was a virgin until you broke me," I said with a sexy tone.

Ken gave me a shocked look, then recovered and smiled. It made sense now. He then turned to Randy. "Wait a minute. Those two fingers you held up were a ‘V' for ‘virgin' not your way of complaining because you were going second." Randy nodded. Ken looked back at me. "He must have been able to tell when he was going down on you because he signaled me right before I mounted you."

He pulled his cock out and looked down. There was a bit of blood on the pillow it turns out, which he commented on. He asked why I didn't tell him.

"I don't know. I think it's because I didn't think you'd believe me. I didn't think I had a cherry even until I felt that monster go in."

Ken said, "Well, we're going to give you a great first time tonight. It's our pleasure!"

"I can't believe how lucky you are," Randy said. "Now even if I get sloppy seconds, you won't leave any tread on it for me," he teased. "Come soon, dangit, and leave some virginity for me!"

I laughed as I felt a particularly deep penetration deep inside me and cringed. "There's none left. My pussy will never be the same."

"She'll be great for you too, trust me," Ken said and smiled at me as he put is cock back in and sheathed it to the hilt. "I want to come. I'd hate to wear you out too soon and make you too sore."

I looked at Randy and saw that pouty look of regret on him. I reached down and grabbed his cock. "Come on, Randy. He just broke it in and made it good for you. Give me a chance and I promise I will please you, too." Randy loved that, I could tell, and his precome oozed out as I slid my grip up to the head of his shaft. "I'm still half a virgin anyway. Maybe you'll get really lucky tonight. I guarantee my asshole is tight for you. Nothing's been shoved in there yet."

"Oh god baby, don't tease me like that," Randy said. "I'll come now!"

Ken began rapid thrusting again, and soon I was building up again near a climax. Then suddenly it happened, and I had my first orgasm from sex. It was the best one I had ever had, and it must have lasted 30 seconds at least and left me weak. I shuddered and babbled as I convulsed. My pussy spasmed around Ken's cock, bringing him closer as well.

As my orgasm subsided, it was time for me to focus on pleasing my new lover. I concentrated hard on my pelvic region. I began to contract my muscles and grip the intruding member. I had learned this through my overactive masturbation habit, although gripping the seemingly largest cock on earth was different than my finger. I was so stuffed it made it hard to grip him. I think it would have been much harder at the beginning of the fuck fest, before I was stretched out so much.

"Oh my god, I'm almost there," Ken said. He leaned in and laid down on me, flattening my breasts. It felt good to hold him close, and his weight did not crush me. I saw a look of concentration on him, then he gave the cutest face that looked like he was in pain. "Uh. Uh uh," Ken muttered, and his whole body jerked as he poured himself into me. I couldn't feel it inside me yet, but I could tell Ken was pumping a huge load of come deep into my pussy. After about five contractions with his cock all the way in, he began to pump in and out and finish ejaculating., coating my deflowered vagina with sperm. I could feel the cock flow in and out much easier from the lubrication of the come, and his penis started to soften, giving my more room to spare inside. I was on the pill by the way for other reasons, and as I reflected on that, I remembered that Ken knew that from our discussions at the gym of medications and so forth. How convenient! I was happy I was getting a ride without a condom and receiving his load. I wanted the most realistic experience my first time.

Ken pushed his cock in deep one more time, then pulled out quickly. I heard a deep slurping sound as my vagina had formed a tight seal around his cock, and he suddenly left me vacated. A good amount of Ken's spunk came out with his cock and flowed down to the pillow and pooled up between my butt cheeks. Ken stood over me, and I could see the semen and leftover blood on his glorious cock. I wish I could see my pussy at that point, since watching come ooze out was always one of my favorite moments in a porn flick.

I was very curious, so I reached down and stuck my finger in. I didn't recognize my own pussy. The hole Ken left was enormous, and I knew I could fit four fingers in it if I wanted to. I pulled my finger out and looked at it. It was covered in come.

Ken picked up the corner of the towel to wipe my vulva. I put my hands on the floor and lifted my butt off the floor and shook it to let his load ease out. For some reason I thought it would be cute. Ken loved it, I could tell. "Oh yeah, here comes the mess." Ken admired my gaping, open pussy that he had conquered, and it turned him on to see his come pour out. My nice ass and tits were shaking and jiggling in a sexy way. Soon I stopped and laid back down, without the soiled pillow this time.

"Spread your legs wider, Lucy," Randy said as he came around to take a look. "Nice job, buddy, you broke her in well. Her pussy is still hanging open!"

Randy took Ken's place and to my surprise leaned down and kissed my clit. He began a light caressing and licking of my whole vulva region, then he slipped his tongue inside. Ken sat next to us watching, spent for the moment.

"Are you too sore to continue after that thorough fucking?" Randy asked.

"There's a dull ache that may never go away, but it gets easier with every thrust," I answered. No way was I done receiving pleasure yet!

Apparently my sloppy vagina and remnant of another man's come did not bother Randy, because he began performing great oral sex. It wasn't long before he took things to the next level though. I felt a lubed finger press against my asshole. Now this was something new. I had never explored this before! I was nervous but didn't want him to stop. Randy didn't apply much pressure and his finger didn't go in for a while. He just sort of pressed it there and let my cute little hole spasm for a while as it worked its way in. Soon it passed the sphincter, and for the first time something went into my ass the other way. I gripped him tightly with my inexperienced ass. I had yet to learn the fine art of relaxing when being anally penetrated.

Randy left the finger in my as I got used to it. Ken excused himself to wash the lube and other fluids off his cock. The finger in my ass definitely did not feel as good as it would in the pussy, but it was weird and exciting. It felt good in a different way.

Randy began to slowly pull his finger in and out of my ass, and periodically he would apply more lube. The discomfort I felt initially was gone, and the finger felt quite good. I was used to it, and the tightness in my ass was gone as the internal involuntary sphincter relaxed and dilated.

"You got used to that quickly, Lucy. Are you really an anal virgin?"

"Yes. I am just a talented one," I quipped back.

"You are ready for cock anytime now."

I looked at his large penis and compared it to his tiny finger. "Don't I need to work my way up to that?"

"It doesn't work that way. Your ass is used to any penetration, and that is all that matters. Watch," he said and held up two fingers. He put them in me, and there was no pain at all, although I could tell I was fuller. He was right. Ken was back in the room watching with interest. "You have a great body, and I am ready to enjoy it now."

His confident and commanding voice turned me on, and I was ready to take him. "Do you want to try my pussy first?"

"Of course, no question."

I rose to my feet and said, "Will you take me doggy style? When I masturbate, I often think of someone fucking me like this. In fact, I think I have masturbated thinking of you fucking me like this," I said and smiled. These studs might have seduced me into giving them my virginity, but really it was me getting my fantasies fulfilled today.

I got back on the couch, and there was just enough room for me to get on the couch with my knees just barely on the cushion still. The couch has a small back, so my head rested comfortably on the top of it. I shook my ass a little and got comfortable. I was glad I had been working out a lot lately, so I was comfortable in this position with my ass on display. I might not be 5'2" and petite, but I know I had a great ass, and just as soon as I thought that, both men told me how great I looked in this position.

Randy was able to stand off the couch and fuck me, with his cock aligned perfectly with my waiting ass. I felt his hands grip my hips. I looked over my back and saw him with a big grin on his face as he brought his cock to my pussy. I felt a now familiar blunt pressure against my lips, then Randy penetrated me. It felt heavenly. There was no delay or painful, slow penetration this time. Randy slid in easily and began thrusting into me with a steady, unimpeded pace. I gripped his cock with my pussy, enjoying the sensations it brought me. I could tell it was a smaller cock, but it still brought me great pleasure. It was fun to be able to focus more on gripping him since there was more room, and not be distracted by the emotions and pain of a first time.

Each time he penetrated me, his hips bumped mine and sent a ripple of what little fat my ass had on it up to my lower back. The vibration propagated up my spine and jarred my large, natural breasts forcing them to jiggle. My nipples brushed against the coarse fabric of the couch at the end of each thrust into my pussy, turning me on even more.

"How is she?" asked Ken as he looked on, his penis beginning to rise again.

"Spacious," Randy said and laughed. "You're awesome, Lucy. I have to be honest here. I wish we'd have done this before the week you are leaving."

"I wouldn't have had the nerve to do it if I had to look at you every Sunday, Randy. This is the only way I lose my cherry in a threesome to two guys that teach Sunday school to minors. Shame on you both, by the way," I said in a sexy, joking voice.

Randy began to stoke me faster, and I was moaning like a whore in pleasure. I felt so great. I couldn't believe I had waited this long to have sex. And at that point, I knew in my heart I would be having a lot more sex in the future, wedding or not.

Ken was smiling at me again and running his hands through my hair. He looked back at Randy. "She's ready. Give it to her." He moved his hands to my ass, and I felt him pull my cheeks further apart, exposing my asshole a little better.

Randy took his cock out. I protested. I wanted that cock inside my pussy. I looked back and saw Randy applying lube to his cock. I knew what was happening next. Once again, my confidence evaporated and I felt that nervous feeling a virgin feels.

"Easy does it, Lucy. Let us know if you need us to stop, okay," Randy said as I felt his cold, lubricated head contact my anus. "But I think you are ready and this will be no problem."

Randy pressed forward. I felt a painful stretching sensation as my asshole resisted. It wasn't bad, just a dull ache. After about 30 seconds, Randy pulled back and applied more lube. He then pushed forward again. This time he opened my first sphincter that was under my control, but my inner ring resisted. I again felt a small burn as he tested that barrier but did not pass it. He pulled out and pushed back in to the same point. He did this about five times, each time causing a little burn as my sphincter protested the large object trying to pry it open. The next thrust, he did not pull back but left his cock there, applying a steady pressure. Quite suddenly, my ass opened completely around his cockhead, and he drove past, burying about three inches inside me. Oooof," I moaned from the sharp pain of my sphincter surrendering completely and being impaled. Randy drove in further and left his cock almost completely sheathed. My ass was smasming against the intruder, and it hurt. Gradually it subsided and my asshole stopped panicking. Randy knew this was happening, since he apparently was a seasoned ass fucker. The cock must have remained inside me for about a minute before Randy pulled it out. My ass gave a plopping sound as the head caused a little pain once again pulling out of my ass. Overall it was bearable. Just like my cherry, I knew I had to endure it for more pleasure later.

"Now it will be much easier," Randy assured me. Sure enough, this time when he put his cock inside, it went into me without causing hardly any pain at all. He began to slowly fuck me, taking about five seconds per thrust. This time he did not pull his cock all the way out past my ass ring as he withdrew, allowing a more pleasant fucking until I was more used to it.

Randy continued to stroke my ass, and Ken played with my nipples as I remained in a sexy doggy style position. Randy probed in and out for a few more minutes, gradually picking up his pace and sinking his cock in now all the way. Soon he started pulling out all the way with each stroke. I was pleasantly surprised to feel none of the pain from before as his cock completely escaped, then drove back into my tunnel, testing my elastic opening. I was fully relaxed and dilated and enjoying anal sex. I found that when I wanted, I could now contract my ass muscles around the cock and grip it, similar to how my virgin pussy was doing this moments before. I experimented with different times and lengths of contractions, and Randy voiced his approval, clearly able to tell what I was doing.

"Check it out," Randy said. Ken peered over and looked behind me and murmured his enthusiasm.

"What is it?" I asked.

"I could barely see your asshole and tell there was a hole there before, but now it is pretty gigantic," Randy said. I could tell he was right just by the waft of cool air I felt enter each time he withdrew, along with the slurping sound my ass gave each time the cock pulled out.

I looked down and saw that Ken was almost fully hard again. He was sitting on the couch now and was slowly stroking his cock as he watched. He was turning me on, and I decided to take things to the next level and try something new. I had seen this in porn and had always wanted to try it. We'll I had always wanted to try a lot of things I guess. I hoped they were not too homophobic for it, since they would be awfully close. It turns out they weren't. They'd probably even done this together before.

"Ken, my pussy craves your cock again. Do you want to put it in me?"

Randy was about to protest. "Don't worry, I told you I'd please you, and I will." I think Randy suspected what was happening because he suddenly got very enthusiastic. I came back to my feet after Randy's cock left me ass vacant again. I moved over one cushion, straddled Ken, picked his cock up and brought it to my hole, and slowly slid down. "Oh yeah. God I missed that already," I said dreamily. I was a size queen already. I looked over at my shoulders and Randy was standing there. I whispered in Ken's ear, "Spread my cheeks for me and let's see if he gets the hint."

"You think you are ready for the double penetration?" Ken asked.

"We'll see. I hope so. This might be my only chance to try it, you know."

"Come on stud, let's go," I said as I looked back at him and blew a sweaty strand of hair out of my face. I felt my cheeks get opened wide again. Ken held still for a minute with his cock buried and Randy inserted his into my ass. The feeling was incredible.

"Holy shit, that is intense," I said. The fullness was amazing. I never thought I could feel so full. The men started stroking slowly in their own rhythm, and I could feel them rubbing against each other, pulling me in all different directions. Each cock seemed to grow in width by 50% as they took space away from each other in my pelvic region. Every nerve ending in the whole area seemed to light up at the same time.

I actually had an orgasm, which completely surprised me. I didn't even sense it coming hardly. The men continued through it and stroked me for about two minutes before I looked at Randy and said, "This is awesome, but you can come any time. I don't know how much longer I can take you."

Randy said, "I want you to tilt your head to the side and open your moth for me and take my load, okay." It was more of a command than a question, and I obeyed, eager to taste come for the second time in my life, this time from a real man.

Randy pulled out of my ass and came around to face my side. His cockhead contacted my outstretched tongue, and I felt a hot fluid suddenly and with a lot of force rocket into my mouth and strike the back of my throat. I then felt a warm sensation spread down from there across my tongue all the way to the tip as his first spurt coated the bottom of my mouth. Then he proceeded to milk his cock and shoot off another five or six volleys into me, and some of it spilled down the corners of my mouth. It was a huge load, built up from arousal and frustration while watching Ken fuck me first. I caught most of the load and let it sit in my mouth for a moment as I enjoyed the taste and texture, then I swallowed with several gulps. It was a large load, and definitely bigger than the one load I took in college. Both men seemed surprised. I had gone from virgin to a sex fiend with the whole anal, DP and facial events. I did not take his cock into my mouth. Randy was content to hold it and shoot off for me, probably since he was in my ass moments before.

"Oh fuck yes," Randy exclaimed, and then he walked away and disappeared behind the corner.

Most of the load was gone, but I could feel a glob in the corner of my mouth on my lip, and I knew there was a large drop of the viscous fluid slowly trailing down my right breast. I felt like such a dirty whore, but at the same time I was never surer of myself. This is what I loved doing. I was having the time of my life, and I refused to stop and feel guilty. I also never felt sexier, and my confidence was shining through to the men.

I turned my attention to Ken again, and continued to rhythmically lift and lower my hindquarters on him and slowly ride his cock. "Did you like watching that?" I asked him and smiled.

"Heck yes. The dirtier you get, the more it turns me on."

I intentionally had left the come on my lip and breast still. My tall frame and long black hair enabled me to actually look slightly down at Ken, with my hair all around and hiding everything else from his view, putting him in our own little world. I was grinding my crotch down on him, taking his cock, milking it with my pussy muscles, and rocking my hips back and forth, giving him a great fuck. I could tell he loved it. I was glad I had watched all that porn and read Cosmo so I could be as skillful as possible on my first time.

"Oh yeah, Lucy. I love fucking you."

I looked over my shoulder to make sure Randy was still not in the room. "I've always wanted to do this, so don't freak out," I said and smiled. I looked down at my nipple, and took my finger and wiped off the goo, then transferred it to my mouth. My tongue took care of the sticky drop on my chin, and smeared it all around. Ken laughed as I did this. I very slowly leaned in to kiss him, giving him plenty of opportunity to object. He did not. My lips, smeared with Randy's semen, met Ken's. My kiss lingered for a moment as I let him begin to taste and smell just a hint of sperm, then I opened my mouth and our tongues met, and we kissed passionately. The rest of Randy's potent load that I had never swallowed was mixed between us and shared, and the strong spunky aroma filled our mouths. Ken seemed to not mind it. I could tell it was his first time. We broke our kiss off, and he licked his lips and swallowed, happy to have tried it, but eager to dispose of the evidence and move on.

I swallowed too, then said, "Okay, I think it's just us again," and laughed. I kissed him for about three minutes as I worked him with my pussy muscles, and soon I felt Ken climax in me for the second time, and about that time Randy came back from wherever he had gone off to.

I sat on his penis for a couple minutes and felt him go soft inside me. At this point, I was completely satisfied. The flames that had built up inside my virgin pussy for so long were finally extinguished, at least for now. I leaned forward and allowed the spent penis to slide out. Both men were speechless and just enjoying the moment post-climax.

I slowly got to my feet, found the towel, and was going to wipe up the semen that was already outside my pussy. To my surprise, there was none. I must have milked him dry the first time! I then grabbed my jeans and shirt and put them on, along with my heels. I had my bra and panties in my hand with my keys. Suddenly what felt like a huge glob of hot come in my pussy leaked out and begin to run down my leg. I guess he had just shot his load deep enough to where it took a while to work itself out. I was back in the drab clothes with no fashion sense, and my nipples were not showing through from my braless natural breasts. My sexy body was covered like before, but this was not the same Lucy. This time I beamed with confidence, and I just knew I was sexy. That flushed, glowing, post-sex look probably helped a little too.

"Thanks guys, I needed that," I proclaimed. "You hit this real good."

Ken had stood, and I grabbed his muscular left ass-cheek on my way out as I gave them both a huge smile. "Come visit me, boys."

And then I left without a hug or a kiss or even a goodbye. Just like that. So much for the clingy virgin!