Weeend of Sexual Surprises

April 3

For those of you didn't read the first part of my journal: My brother Artie invited me to visit him at college to celebrate my 18th birthday. He told me it would be a Weekend of Sexual Surprises, but I had no idea what that meant until I got there. Friday evening after dinner, I got my first surprise when a cute Chinese lesbian joined me in the shower, then tied me to the bed and gave me a tongue-lashing I'll never forget. Now I'll tell you what happened next.

After the Chinese Lesbian left the dorm room and I'd put on my nightgown, I was exhausted and could barely move or talk. That's what a three-minute-long-orgasm will do to you. So Artie and I kissed, curled up in bed together, and went to sleep. I love to share a bed with Artie. When I was a very little girl, I always wanted to sleep in Artie's bed, even though I had a perfectly good bed of my own. Mom and Dad would put me to bed and as soon as they left the room, I'd get up and move to Artie's bed. We weren't doing anything naughty, of course, just being close to each other and feeling each other's warmth and sometimes hugging. Always, just before we went to sleep, we'd kiss, just like we did that Friday night in the dorm. Even when I was four or five years old.

That Friday night, we'd been sleeping for a long while when I felt Artie get up, probably to go to the bathroom. I dozed back off, and he came back to bed. But soon after he got back in bed, it seemed something was strange. There was a hand going up my leg, and he was naked and had a hairy chest, which Artie doesn't. Even in my sleepiness, it didn't take me long to realize that the guy in my bed wasn't Artie. A quick touch told me that his cock was hard and already had a condom on. This definitely wasn't my brother.

So this was my second Surprise. I was going to get fucked by a complete stranger, in the dark so I couldn't see who it was. And he had a thick meaty dick, just like I like it. I tried to talk to him, to ask him who he was, but he wouldn't speak, and he put his fingers on my lips to tell me not to speak either.

The Stranger put my hand on his cock, motioning for me to rub it. He kissed me, gently at first and then more intensely and his tongue entered my mouth. He lifted my nightgown to my neck and massaged my boobs while we kissed. Then he broke the kiss from my lips and started kissing, licking, and eventually sucking my nipples. Each suck made my clit quiver.

I lifted my butt and he took my panties off and I spread my legs so he could put his fingers inside me and work directly on my clit. The Stranger moved his head back to my mouth and we kissed some more while his fingers brought wetness from inside my pussy up to my clit. My clit grew harder and harder and my breathing grew heavier.

Then the Stranger rolled me over onto my stomach and I put my butt into the air, waiting for him to enter me doggy style. But instead, he used his cock to massage my pussy and my clit. The shaft of his cock rubbed my clit and inside of my pussy lips, but for the longest time, he wouldn't entered me. His hands massaged my butt cheeks.

Eventually he relented and entered me, very slowly, and, when he was inside, began pumping. He put his hands around my body and massaged my nipples while he went at it. The pumping got fast and furious and I was panting and moaning. It was hard to keep quiet, but it was the middle of the night and I didn't want to be screaming.

After a long time, I rolled the Stranger over and got on top. He caressed my boobs and massaged my nipples with my thumbs while I rode him. Hopping up and down, panting and sweating like a pig, I put my fingers on my clit while I was still riding him. I came, my second time that night, covering my mouth with my other hand to keep from screaming. When I finished cumming, I collapsed onto his hairy chest.

After a brief rest, I dismounted, took off the condom and jerked him off. It didn't take more than a few strokes until he came, getting the cum all over my hands and his stomach.

I whispered "thank you" to him, but again, he put his fingers to my lips, and I was quiet. The Stranger kissed me, got out of bed, put on some clothes that were on the floor, and left, and Surprise #2 was over. Out the window, I could see that it was nearly starting to get light.

My breathing calmed. I rearranged my nightgown but I couldn't find my panties. I threw the dirty condom out of the bed and used my nightgown to wipe the wetness from between my legs.

Artie came back into the room and climbed into bed with me. As he gathered me up in his arms, I asked him who the guy was. Artie gave me a quiet "sshhhh", and told me to go to sleep. My hand was all wet and sticky, so Artie wiped it off on the sheets and gave me a sweet brotherly kiss on the forehead. I wrapped myself around him and we went back to sleep as Artie stroked my hair.

In the morning, I woke up before Artie, so I stayed cuddled in his arms for a while, hoping to let him sleep. But I really needed to pee, so I got up, put on my robe and went to the girl's bathroom. I peed, brushed my teeth, and got in the shower. This time, no cute lesbian joined me and it was just a normal shower. Too bad.

When I came back to the room, Artie was up. I tried to pump him for details on the Stranger. Who was he? Was he somebody we'd had dinner with? But Artie laughed and wouldn't tell me anything, other than that he hoped I enjoyed it. He wouldn't give me even the smallest hint. He told me about a "zip-less fuck" which is an idea that comes from some book in which the heroine fantasizes about being fucked on a dark train in a tunnel by a complete stranger that she never sees. I didn't know that my brother was literary, but I guess there's always time for porn.

Artie and I changed the sheets on the bed. They were a mess. We took the dirty sheets downstairs to the laundry and went outdoors to lunch, headed toward Artie's favorite sandwich shop downtown. Every time we walked past a guy on the street, I wondered if he was the Stranger. I looked for hairy chests.

At lunch, I gave my brother the complete story of the Lesbian and the Stranger, enjoying reliving and telling every detail. I tried to describe what the Lesbian had done to my pussy and how it felt, how she had kissed my fingers and toes and tied me up, and how she had teased me until she finally went to work on my pussy. We talked a lot about what she'd done to my asshole and how it had turned me on, and how it had shocked me into orgasm when her finger went up my ass. This time Artie answered my question from last night – he had never put his tongue up a girl's asshole and wasn't sure he wanted to. I was disappointed.

I told how I had discovered that the Stranger wasn't Artie, that he had a hairy chest, and how he rubbed his dick against my pussy before he fucked me from behind, and how I had ridden him to orgasm. I tried again to get some info about the Stranger, but Artie just smiled at me and wouldn't tell me a thing.

Walking back from lunch, Artie teased me, pointing out strange-looking guys and asking if I thought they were the Stranger. One guy was about 5 feet tall and skinny, another had a big beard and potbelly and looked like Santa Claus, and another was flamingly gay. There was an old man, about 80 years old, walking with a cane. Each time Artie pointed out a ridiculous possibility, I punched him in the shoulder and he laughed.

I kept bugging him, so eventually Artie agreed he'd tell me about the Stranger. We sat on a park bench. He leaned forward, like he was going to tell me a secret in great confidence, then he pointed out somebody across the way. "That's him," Artie said, very seriously. "Do you want me to take you over and introduce you?" I looked closely and it was a very butch lesbian wearing farmer overalls and work boots. I punched Artie twice that time, and he laughed extra-hard.

I never succeeded in getting Artie to give me any details about the Stranger. So I didn't bother to ask what the next surprise was because I figured he wouldn't tell me. I was surprised when he brought the topic up and started to tell me what would happen next.

Artie told me that he had a friend who was a very nice guy, good looking, clever and friendly, not gay, but very shy around girls. He was a virgin and had probably never even really kissed a girl. I was going to spend the afternoon teaching him about sex and removing his virginity.

What fun! I asked Artie how this had been arranged. Did he just say "My sister is coming up to visit this weekend. Would you like to fuck her?" Artie laughed and said that, yes, it had been pretty close to that. The Virgin, he said, couldn't wait to meet me. He'd been jacking off all week in anticipation (I shouldn't tell the Virgin that I knew that), but Artie had warned him to give it a 24-hour rest so that he'd been ready for me.

We went for a short walk around campus to get some air and enjoy the spring weather. Artie showed me where he had classes, where the labs were, and where he gets good pizza. Then we went back to Artie's room and Artie gave me a handful of condoms. I asked him what I should wear and we decided that regular clothes would be less intimidating than the sexy underwear I had brought, so I didn't change. Artie left and came back and introduced the Virgin. We shook hands (How strange was that? Have you ever shaken hands with somebody you were going to fuck?) and my brother left.

The Virgin was, indeed, reasonably good looking and very, very shy. He was a little tall and a little thin. I broke the ice by giving him a nice long sexy kiss, without tongue, and telling him that this time together was just for him. There was nothing he was supposed to do for my benefit, and that all he needed to do was relax and let his body do what it knew how to do.

I figured it would relax him to talk a bit. He told me that his name was Howard. I wondered if this explained why he was a virgin, but I figured it wouldn't enhance the mood to say that, so I held my tongue. He said he was a freshman and majoring in electrical engineering. I held my tongue a second time. I asked him where he'd gone to high school, and he said he was home-schooled. For the third time, I held my tongue. Poor guy – three strikes against him.

It turned out that he really was a pretty decent guy once you got him talking. He had a nice smile and a bit of a sense of humor, making jokes about his lack of experience with girls. Howard wasn't any kind of a reject and there was no reason for him to be without a girl. I don't mean that I would have dated him myself, of course, but I'm sure there were plenty of girls who would appreciate a home-schooled freshman electrical engineer named Howard.

Then it was time to get to business. I lifted his shirt over his head and ran my hands over his chest and kissed him some more. He didn't really know how to kiss, so I didn't press the issue, and I guided him to the bed and took off his shoes.

I figured that he was probably going to cum quickly the first time and he was probably worried about it, so I'd let him cum now and then get him hard again for the actual fucking. I massaged his crotch outside his pants and could feel that he was hard, so I started to open his belt and told him I wanted to see his hard cock and rub it and make it cum. He volunteered that no girl had ever done that for him before, and he had often thought about how nice it would be.

I pulled off his pants, laid him down on his back, touched his cock gently and started rubbing. Howard told me I should slow down because it would be over soon if I didn't, so I slowed down and let him enjoy the sensations. It was a pretty nice dick, average length and thickness, circumcised, and pointing up at a sharp angle. When I thought he was ready, I speeded up and I pumped him dry and the cum landed on his stomach in big squirts. Howard thanked me profusely as I wiped him dry with his shirt. I licked his cock to clean it and I could feel him tense up with surprise. Howard had a big smile on his face.

I complimented him on how good his hard dick had looked, kissed him on the cheek, and asked if he'd take off my clothes for me. He was shy at first and seemed reluctant to touch me, so I assured him that I wanted him to take off all my clothes so that I'd be completely naked, and I wanted him to look at and touch everything, especially my boobs and pussy. He lifted my shirt off and I turned around so that he could unhook my bra. Then I faced him and took his hands and put them onto my boobs and showed him how to pinch and massage the nipples. I stood up and asked him to take my jeans off. He unzipped them and took them down and I stepped out of them, took off my socks and dropped the panties myself.

We were both buck naked now, and I gently held and stroked his cock. It was still wet but it was getting hard already. I laid down on the bed and opened my legs and told him I wanted him to look at my pussy. I opened the lips and showed him the clit and showed him how I like it touched, and he touched it. After asking if it was ok, he put his finger inside me. "You don't have to ask," I said encouragingly. "I want you to touch me everywhere."

He was less shy now. I didn't have to tell him to suck on my nipples-- I guess that's instinctive. I gave him a little fine tuning on how not to suck too hard, and how to kiss and massage the boobs the best way. Howard was a fast learner and was soon working my nipples like a pro.

Howard the Virgin was fully hard now, and I could see he was ready to fuck. So I took out a condom and put it on and invited him to climb on top. I guided his cock into me and he started pumping. I moved my hips in rhythm with him, and I had to admit it felt good, in a relaxing sort of way. I massaged his back a little, and when I dug my nails in, he started pumping harder and faster, then came with a shudder and collapsed against my chest. I kissed him on the top of his head, thanked him, and reminded him to hold onto the condom as he pulled out. I cuddled in his arms and congratulated Howard on being a virgin no longer.

We rested a while, and I figured this was a good time to teach him how to kiss. So I brought his lips to mine and showed him what to do. My tongue entered his mouth and he learned to let our tongues play together. Pretty soon, we were doing some reasonable making out, and we both enjoyed it. I put his fingers between my legs and my fingers around his wet still-soft cock and we both gently massaged each other while we kissed.

Pretty soon, I could feel him getting hard again so I got more serious about the cock-rubbing. When he was fully hard, I put another condom on him and climbed on top. I put his hands on my boobs and rode him for a while. I showed him how to hold my boobs and how to use his thumbs to massage the nipples. Then I flipped him over and he got on top and pumped. He wasn't the most experienced or confident sex partner I've ever had, but the screwing was pleasant and after he came, he remembered to hold onto the condom.

I congratulated Howard the Ex-Virgin and told him he'd done a good job, and we laid together for a long while with his fingers on my pussy. I took it as an accomplishment that he would put his fingers on my pussy without me telling him to do it. Finally, we got up, got dressed and said goodbye. This time he gave me a kiss instead of a handshake.

As he got ready to leave, I gave him a final piece of advice, "Just remember, Howard, girls want sex as much as guys do." Howard laughed, and had the biggest smile I'd ever seen. He thanked me and left.

In a minute or two, Artie came back in and we went out for ice cream. As we walked, I told him the whole story, and how successful I'd been in bringing Howard the Virgin out of his shyness, how he'd cum three times, fucked me twice, and gotten pretty good at boob technique. Maybe I'd found my calling in life – I should be a prostitute specializing in rescuing shy guys from virginity. It's not exactly Mother Theresa, but in a small way, it would be helping mankind. LOL

You know, it made me think. It had been a long time since I'd had sex with a virgin. Maybe two years. I always pick partners who are experienced and (hopefully) talented in bed. But I really enjoyed the experience with Howard. Watching his face and seeing his excitement at the new sensations was something very different than a normal fuck, and I really liked it. I told Artie that, when I got home, I'd find a virgin every now and then and make his day. Maybe I'll gang-bang the high school chess team!

My brother and I ate our ice cream. We shared a large hot fudge sundae on rocky road ice cream, and argued about who'd get the cherry. We decided to split it.

After we got back to the dorm, Artie brought out his computer and told me I needed to get myself prepared for the fourth and final Surprise. He went to Google and looked up "bukkake". I thought I'd heard of every possible perverted thing to do (most of which I'd actually done), but I had never heard of a bukkake. For those of you who don't know, it's a Japanese thing where a naked girl is surround by a bunch of guys and they cum all over her. They can jack themselves off or she can do it for them. The goal is to get as much cum as possible all over the girl. Artie told me that this was to be the highlight of my Sexual Surprise weekend. I was going to be "the center of attention" at a bukkake.

I was stunned. Who knew that my quiet innocent brother knew about this stuff? It's amazing what you can learn in college. The more I learned about a bukkake, the more it sounded like a lot of fun, and I was getting pretty excited. My pussy was still a little damp from the afternoon's adventures, and now it was getting wetter yet.

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It's getting late and I've been writing a long time and I'm tired. It takes a lot longer to write this stuff down than I thought it would. Come back in a few days and you can read the rest of it-- you don't want to miss hearing about the bukkake. Now, I'm going to bed as soon as I find a new battery for my vibrator. Maybe Dad has one.