Love Tax

"You're still a virgin aren't you Sean?" whispered Regina to me as she saw I was ignoring the professor's lecture.

"No," I said trying to sound insulted even though it was true.

"Thought so," she said with a smile. I'd known her since I started taking this class and she actually had become something of a friend. But she was mean and nasty to me, while she did help me out a few times with class notes and homework. She was smart, but I never even once considered dating her. "I could help you out with that if you want," she said chewing on the end of her pen.

"With you? No way in hell," I scoffed and returned to try and pay attention to class.

She leaned in close and whispered, "I never said with me..." I looked back at her and she pointed a finger at the girl I'd been looking at instead of paying attention in class. I'd taken this boring Literature class in the first place just to try and get closer to Shawna.

I looked back at her long silky black hair and my pulse quickened. "Are you saying..." I started a little too loud. I tried to collect my jumbled thoughts and whispered back in shock, "She's a prostitute?" I didn't really know her at all. I'd had one class with her last semester and only briefly talked with her once, but I was bitten by the love bug hard that first time. I thought our first meeting went well, but then she seemed to go out of her way to avoid me. I figured I must have made a bad impression, but from what I knew of her she was very shy and into reading, very smart and always at the top of the class, but even when I'd sat right next to her she always ignored me completely. With all that I just couldn't fathom that she would be the type to sell her body to men for money.

"Hey," Regina quipped, "college is expensive." She left it at that for ten minutes and I struggled with my morals. My heart said pay whatever cost it took to be close to Shawna, but my brain said if what Regina said was true she must have slept with dozens or maybe even hundreds of guys. And if that was true, I'd just be a nameless John that she could never care about. "Two hundred dollars and I'll see to it she comes over to spent the night," she eventually said and my mind became clear.

"Deal," I said like I was making a pact with the devil. "I don't have it on me, but I'll bring it tomorrow."

Regina smiled, "I trust you. And in good faith, I'll tell her to come over to your place tonight at nine." I couldn't concentrate the rest of the class and just watched Shawna leave the classroom like any other student as Regina ran up to talk with her as they left.

I decided to skip the rest of my classes that day and cleaned up my small dorm room. I hid away my porn and suggestive posters, did my laundry, and even vacuumed the floor and changed the sheets on my bed. Then I showered off and dressed as casually as I could and texted my roommate to go find someplace else to sleep tonight. That's not usually a problem for him, as he rarely used our room in the first place. If he didn't have a girlfriend he had tons of friends in several frats and often crashed there for some overnight party or another.

Everything was set for hours as I just anxiously waited until nine o'clock. I was watching every tick of the clock for the last half-hour and pacing back and forth madly until I finally heard the knock on my door. I ran to it and looked through the peep hole, as if I didn't already know who it was. In the distorted fish-eye lens I saw Shawna's face up close with the rest of her body distorted down and away. She'd been dolled up as I'd never seen, with long lashes and lots of make-up. Her body shimmered in a green skin tight dress. I hurriedly opened the door and she quickly came in as if embarrassed to be seen outside as she was. I guess she didn't want to get caught prostituting or she might get thrown out of school.

"Hi Shawna," I said dumbly.

"Hi Sean," she said softly, as I almost always heard her talk, but this time she said my name. It was just excited that she even knew my name, and my heart which was already racing skipped a beat.

She walked in and looked at my room, and I didn't know what to do next so I just said, "Make yourself comfortable." She moved in and sat on my bed. I was too nervous to suggest jumping right to the reason she was hear so asked, "Would you like something to drink?"

"No," she said and then took a deep breath as if she was nervous also. "I'm ready for you now, so I want to fuck." The words sounded so strange from her delicate lips that I almost couldn't believe it, but to prove it she unzipped her dress and revealed she was wearing nothing at all underneath. No bra or panties, so was now completely naked as she kicked of her high heels.

Not only was I a virgin, but I'd never gotten past kissing in high school, so now only a few months into college this was completely foreign territory to me. I was frozen looking at her small but nicely shaped naturally pert breasts and her trimmed little bush between her long thin legs. I must have been petrified for too long staring at her because she said then worried, "Is something wrong? Am I... not pretty enough?"

I couldn't believe she might think that. "No, of course not. You're just so amazing that I couldn't stop staring." She blushed and turned her head away and I decided I needed to act. I swooped down next to her and took her chin in my hand, turned her head toward mine and kissed her on the lips gently for several moments. It wasn't a passionate kiss, but a loving one. When we parted she decided to take over and grabbed at my shirt and pulled it off my head, threw it away to grab at my jeans. I stood up to help her and soon they were roughly pulled down along with my undershorts and I was naked with her as well.

My manhood was firm and pointed out proudly, ready for action, and she eagerly got to her knees and began slobbering over my knob. She didn't go deep, but sucked and flicked my mushroom head with her tongue hard and fast. I was really excited, but didn't want to cum in her mouth. I was paying two hundred dollars for this encounter, so I wanted to make her mine. I pulled her off and ordered her, "Get on the bed."

Shawna didn't argue and just did as I said. She sat on my bed, laid down, and preemptively spread her legs open to show me her damp gash open for business. I didn't waste any more time climbed on top of her, rubbing my hard cock up and down her moist slit a few times before pushing into her tight folds. I screwed my eyes shut at the tight amazing sensation of pushing into her wetness and she moaned out in a little pain as I did. I had no experience and didn't want to ask stupid questions, so assumed I'd done it a little too hard at first. I pulled back and thrust forward again and found I penetrated even deeper into her. She whimpered slightly, but didn't complain so I just kept at it, each time pushing deeper.

After five or six thrusts I felt the some last part of her open and suddenly fell into her lake of passion and I was pleasantly drowning in her. She gasped out, "Oh God!" and shook as she grabbed onto my shoulders and I felt her womb shudder around my entombed penis.

"Are you alright?" I asked concerned I'd done something wrong.

"No, it's alright," she muttered, but I just looked at her and she said, "You're just a little bigger than I expected." I laughed with relief and she did as well, and it was weird how I could feel her pussy walls vibrate with her laugh around my cock. Then she added, "I'm fine if you want to keep going."

With her permission I did just that. I became an animal, grabbing at her small rubbery breasts and jabbing her insides with my burrowing cock. I just let instinct guide me as I touched and fucked and kissed her body. She was mine for tonight, bought and paid for, so I took and used her completely. I fucked her hard and made her mine as best I could and held out trying to enjoy her to the fullest until my balls could take no more as they screamed for release.

It could be she was just trying to make me enjoy it, but she seemed to be panting and enjoying it just as much as I was, and I hoped she really did. I had fantasized about this moment so many nights since I first meet her, but now I was imagining that I was the best she'd ever had. She'd suddenly announced to me she was giving up prostitution and wanted me to marry her, all while I kept fucking her, and then my will broke. "I love you!" I cried out before kissing her one last time as I wedged myself as deep into her womanly crack as I could and the world when white. I had the biggest orgasm I'd ever had as each and every salty ejaculation squirted into an actual womanly womb for my first time.

When I came back to myself I pulled off of her to allow her to get up and looked down at my shrinking member. I was wet and sticky with my cum and her female lubricant, but also had some blood around my base. "I'm sorry, did I hurt you Shawna?" I asked with concern, but she just turned away from me, put on her heels, collected up her dress and ran out my door before it was all the way on. I didn't know if I'd upset her, or done something wrong, or if she just really couldn't stand me that badly.

I was crazy upset with guilt that I'd taken her this way, but also strangely sexually invigorated at having finally 'done it', and that it was with the one girl I really liked. I was a torrent of confused emotions and hardly slept at all that night. The next day I hit the ATM and withdrew the agreed upon two hundred dollars and went to Lit class and sat next to Regina to pay her. I spied Shawna in the front row as usual, but also as always she never once looked at me as if I didn't even exist.

"Thank you very much," was all Regina said as I handed her the money and then just paid attention to the professor for class. I wanted to ask if I'd messed up with Shawna, or if she'd said anything about me, but I just didn't have the courage. After class ended I decided I would ask her at least if I could still hire her again in the future, but Regina took off to walk next to Shawna for another class.

I ran up to them, ignoring if I made a scene or not, I had to talk to them. "Hey, Regina!" That's when I saw Shawna was handing Regina an envelope. "Wait!" Now upon them Regina turned to face me and put the envelope behind her, while Shawna didn't turn to face me, but stopped walking as well, just waiting for her friend while she was talking to a stranger. "What's in the envelope?" I asked now very suspicious.

"This?" she pulled it out to wave it around quickly, "Nothing, it's just..." and I surprised her by swiping it away quickly. In it was a stack of twenties just like I had handed her, two hundred dollars by the look of it. "Okay, fine! You caught me," Regina said laughing kind of nervously. "Shawna has had a crush on you for months and I saw you staring at her as well, so I trick you both," she confessed. "I told her she could sleep with you if she paid me, same as you."

"So..." I said walking over to force myself in front of Shawna, "You're not a prostitute?"

That freaked her out and she finally looked at me with crying eyes, but still didn't speak. "Pfft..." Regina blew that off, "She was a super cowardly virgin like you until last night. To be honest I wasn't sure if she would actually go all the way with you without me coaching and dressing her up last night. Now, give me back my money Sean."

I had nothing else in my mind but Shana now and scooped her up into my arms right in the crowded hallway and kissed her, fiercely to show her my love for her. To my joy and surprise she hugged and kissed me back. She was crying now, but I could tell they were tears of happiness, and I joined her in wetting my eyes as well.

I think we would have kissed the day away there if not for Regina. "Great. Hello! Guys, I'm going to be late for my next class!" Then I felt her gust trying to tug the envelope away from my grip.

"Here," I said handing her the money. That made her go away and instead of going to our next classes I pulled Shawna with me, holding her hand the whole way back to my dorm room once again. It was like a dream come true. Where before today she would always look away, now she stared only into my eyes, as I did with her. This time she spent the whole day happily and breathlessly in bed with me, and even stayed the entire night this time, even if we didn't get much sleep. In fact she spent every night with me after that and never looked away again.