A Win-Win Situation

It's another day in paradise here in South Carolina. Sunny and hot, a little too humid, but nice for tennis. My girlfriend and I were hitting balls on one of the beautiful clay courts at the resort where we are spending a week together.

We have been seeing each other for four months now, and it seemed like the right time to spend a vacation get-away together. We are staying in a rental condo near the beach, and playing plenty of tennis.

Her name is Susan, but she prefers Susie. Mine is Bob, just plain old Bob.

Susie is 24, a few years younger than I am. She played serious, competitive tennis in college. She played first singles on a very good Division One team, and she did very well. I have played for several years, but I do not have her classic strokes.

We started out today just hitting groundstrokes for a workout. The wonderful location and the excellent courts made it great. The only sounds were the "thwack" of our racquets making contact with the ball.

Susie is so competitive that it wasn't enough. She said, "How about if we play one set for fun?" Right, for fun. I knew better. I told her to serve first, and she won the first game at Love. I held my serve, and the match was on.

When we got to six games all, we agreed to play a tiebreak. If you are not a tennis player you may be wondering how a guy my size can have difficulty defeating a pretty little thing like Susie. Maybe you have seen some professional women's matches on TV, and you have seen the likes of Sharapova blasting winners. Susie is no Sharapova, but she has her competitive spirit (and her good looks).

Before we started the tiebreak, Susie said, "Let's make this interesting. How about a little wager?"

"OK", I said, but I had a better idea than money. "How about if the winner gets their sexual preference tonight, no questions asked?"

She smiled, and said, "You're on!" We had been having sex for a while, but it was what I consider "polite" sex. Missionary position, with quiet, subdued orgasms. I think one of the reasons it was so ho-hum was we used condoms. Delivering my cum inside a woman, through her mouth, vagina, or asshole, is important to me, and I think it is to any man. I think it completes the act for both the man and the woman.

With a prize like this at stake, I played like a demon. I was dripping wet and sucking wind, but I got the score to five-all in the breaker. For you non-tennis people, a tiebreak is first to seven, but you must win by two.

Susie's eyes were blazing; she was not about to let me win. I don't think it was the sex that inspired her, she just hates to lose. It was her serve, and I hit a good return and followed it in. She hit a passing shot that almost knocked the racquet out of my hand, but I put it away cross-court.

My serve now, leading six to five. I was too tired to play a long rally; I had to finish this quick. So I hit a spin serve to her backhand, and charged the net. She tried to lob over me, but I jumped for it, and hit an overhead for a winner.

She thought about throwing her racquet, but her years of tennis etiquette stopped her, and she came to the net to shake hands. We left the court, and headed back to our condo.

As we were stripping off our wet tennis clothes, I said, "Let's shower together." Susie said, "Is that what you want for your victory?"

"No," I replied, "That is just to get started." She gave me a suspicious look, but we went in to the bathroom together. In the shower, we took turns soaping up each other's backs, and I reached around and touched her pussy.

I took a soapy washcloth and washed her between the legs. I pushed my middle finger up her asshole, something I had not even touched before. My finger was soapy, and it slid in all the way. She looked surprised and curious at the same time, and said, "Is that what you wanted to do, put your finger up my butt for your prize?"

I answered, "No. That is just foreplay." I used the removable showerhead to thoroughly rinse her crotch, both front and back. We dried each other off, and I led her back to the bed.

Susie laid down on the bed, and I knelt between her legs and gave her fresh, sweet smelling pussy a kiss. She spread her legs farther apart as an invitation for me to do more. I licked her vaginal lips, and flicked her clit with the tip of my tongue.

I surprised her by brushing her anus with my tongue, and then I just went for it. I licked her asshole, and pushed my tongue as far in as I could.

We were both ready for more, so I asked her to turn over. I said, "Lay face-down, and spread your legs just a little. I am going to get on top, with my legs outside of yours." She reluctantly did as I asked.

I moved into position over her, being careful not to put my whole weight on her. No condom this time, and I was excited knowing that my bare cock was going to go up inside her, and I would get to cum in her, instead of in a piece of rubber.

She said, "Are you going to, you know, do it that way? I'm afraid it might hurt, and I don't want to even try it!"

"Susie," I said, "A deal is a deal. I won, remember?" She didn't try to escape; she surrendered, out of her huge sense of fair play. I put the tip of my cock up against her tiny asshole, and tried to push it in. No way.

I got up and went into the bathroom, but all I could find was some of her lotion. I put some on the head of my cock, and it was pretty slippery. I went back in to the bedroom, and got into position again. I said, "Reach back with both hands, and spread your butt for me."

"That is so humiliating!" I reminded her that I had won, and she did as I asked. This time, when I pushed hard, about two inches of my cock went up her asshole. She gasped, and said, "I don't think -" but I interrupted her by pushing it in a little further.

She said, "Bob, that is uncomfortable", but my answer was to give her another inch.

She practically yelled, "Bob, don't you think that is far enough?" My response was to push it in deeper.

She tried to crawl away from me, but I held her down. I put my hands on her shoulders to prevent her from moving away from me, and also to give me the leverage to push harder.

My cock was about halfway in, and I felt the tight ring of her anus just let go and relax. I could see her face, and the expression she had was a mixture of apprehension and lust.

She was not resisting or arguing any longer, and she whimpered as I pushed up in to her deeper. I am sure that now she wanted it in her as much as I did.

It has been my experience that the first time a woman gets fucked in the ass, she is conflicted. She thinks that it is dirty, but she likes it. She thinks that it is perverted, but she likes it. She thinks that it is humiliating, but she likes it. Finally, she just gives up and admits to herself that she likes it.

"My God, it's up in my stomach!" And I gave her the last two inches. When it slid in, she just said, "Uhh!" She was taking quick breaths, and exhaling sharply with a puff, like a woman in labor. "Good Lord, it's so big!" she whispered.

I held still, with my cock embedded in her pretty ass. I started to gently fuck her, not pulling out but just humping up against her smooth butt cheeks. Her butt is firm from lifelong tennis and weight training, but it is still silky smooth and feminine.

I felt myself getting close to coming, so I fucked her harder, with more in and out. I couldn't hold back, so I pushed all the way in and squirted my cum up inside her. I knew she could feel it, because she gave a little grunt with each spurt.

I don't think she had ever had sex without a condom, so feeling my semen shoot into her was a new experience. The dreamy look on her face indicated that she liked it.

I collapsed on top of her, breathing hard. After a few minutes I pulled my still-hard cock out of her. She had a look that said she couldn't believe what had just happened to her. I kissed her, and went back into the shower to wash up.

We cuddled up and drifted into a deep sleep, spooned together. In the middle of the night, I woke up not knowing why, and discovered that she had my cock in her hand, stroking and playing with it. She hadn't even touched my cock up until then. I think she felt a new affection for it.

We didn't try anything then; we both went back to sleep. At about 7:30 the next morning, Susie woke me up with a cheerful, "Let's go, time to play tennis!" I groaned, rolled out of bed, and went to the kitchen for coffee. She said, "Come on, I booked a court for us at 8:00!"

"Good God. Do we have to do this now? How about 10:00?"

She was relentless, and I dragged myself down the stairs behind her, and we walked to the tennis club. Once on the court, she was a stroking machine. She said, "Same game as yesterday, same bet?" I agreed.

After a short warm up, we agreed to play just one set. I was tired, yes, but that is not an excuse. She just cleaned my clock. She won 6-0. I didn't get a single game.

We went back to the condo, and without a word we stripped down and got into the shower together. We soaped and washed each other, but she paid a lot of attention to my cock. She washed it thoroughly, and rinsed it clean.

After we dried off, Susie led me into the living room, and indicated that she wanted me to sit down in one of the chairs. She knelt down in front of me, and began to give me a great blowjob. I had no idea that she knew how to do that, but I guess college girls do get a liberal education.

I said, "Is that what you want to do as your prize, suck me off? Because I'm about to cum in your mouth!" She replied, "No. That is just foreplay." She abruptly stood up and turned around. She began to sit down in my lap, and I understood what she wanted. I quickly lined up my cock with her asshole.

When it touched her anus, she came down on it hard and fast, and took it up her ass in one continuous motion. I would not have shoved it into her that fast, I would have been more considerate, but she obviously wanted it that way. Her asshole clamped down and squeezed my cock several times. I didn't know if it was deliberate, or an involuntary spasm.

She pressed down hard on my lap, taking every bit of my cock into her. It went in pretty easily, so I must have permanently stretched her yesterday. She started to rock gently, swaying back and forth, and murmuring words I couldn't quite catch. I did hear some things, like "big", and "cum in me".

She reached down and gave my balls a tickle, and then moved up to her pussy. I couldn't see what she was doing, but I could tell she was playing with her clit in the same way she probably masturbated.

In a few minutes she exploded in a convulsive orgasm, grunting and groaning. When she caught her breath, she said, "Now it is your turn" and began lifting up and lowering herself down on my cock. Years of playing tennis and other athletic activities had given her the strength, balance, and coordination to do it.

She was literally fucking herself on my cock, up and down, in and out. I didn't move, I just enjoyed the feeling, and the view. My cock was disappearing up into the crack of her pretty butt.

Soon enough, I whispered, "I'm going to come." She sat down hard on me, with all of my cock up her ass. "Pump it into me", she said. She started to rock and sway back and forth again, and I shot my load into her.

She fell back on top of me, and we stayed that way for several minutes. When we recovered, we went back into the shower together and washed up. We dried off, and climbed into bed together.

As we were drifting off for an afternoon nap, I said, "Remind me. Who won today? I forgot."

She whispered, "We both won." We both fell asleep. When I woke up several hours later, she was already awake and aroused.

She fondled my half-hard cock, and I pushed my middle finger all the way up her ass. There were no objections from her; she just gave me a sweet, affectionate smile. I tried to get her to roll over face down, but she resisted. "I want to see you" she said, and she stayed on her back, and lifted her legs as far as she could.

I moved over her, and tried to find her asshole with my cock. She reached down, and guided it into place. As I pushed, she helped to insert it into her asshole.

We maintained eye contact as it slid up her ass, little by little. She made a grunting sound, like "Uhh!" with each push. It took a couple of minutes to get it all the way in. When the last inch went in, she said, "Yes!"

She smiled affectionately, and kissed me. "I love to feel your bare cock in me. I love to feel your cum squirt into me. I can't get enough!"

I took my time, and slowly, gently fucked her. The only sounds were the steady squeaking of the bed, and her murmuring, muttering sounds of pleasure. Her eyes were closed, but with the first spurt of cum they snapped open and she reached her orgasm as well.

Her expression was pure ecstasy, and her eyes were glowing with lust. She said, "I could feel it. I love it!"

Obviously, life would never be the same for her, or for me. I was looking forward to a long-term relationship.

What a great vacation this turned out to be. We still had four days left!