I took the lead and called Wes. He didn't live at school, he roughed it at the mansion. While we made our own beds, at least threw the sheets on the bed instead of the floor, and ate mysterious food at the cafeteria, his chief asked him what he desired. But I have to say that Wes wasn't snooty. He never knew any other life. I also wondered why, with his breeding, money and fabulous good looks, he could have anyone, but chose me.
Anyway my ten year old car stopped at the gate and I got out and used the phone to gain admission. The house man answered and then checked with Wes and finally with a click, the gate began to swing open.
I headed up the long drive and finally parked between a Rolls Royce and Wes's antique Morgan. I looked back, I think my car made itself small and inconspicuous out of embarrassment.
Wes was on the raised entry waiting. He shook hands with me. That is wise, considering we were on display to everyone in the house. "Come on directly up to my apartment. We're going to lunch there."
He was dressed casual, for him. For me, that would have been dressy. He had on a pair of light grey, thin wool pants and a navy cardigan sweater over a white pique polo shirt. As I followed, I admired his cordovan loafers, shined to a mirror finish. How great to have servants. My, once white, K-Mart sneaks could use a stiff brush and soap.
Apartment? Yes, I had been there before. He had a large bedroom and adjoining was a sitting room, as large as anyone's living room, even boasting a piano.
He clapped his hands in pleasure as he looked me over. "Oh Bobby, I have an idea for our vacation. My family has a villa at lake country in Northern Italy. It's been vacant for awhile, they go somewhere else, I forget where. We could share a nice house at the lake and..."
"It sounds great, but I'm not sure I would want to be so far from my folks for so long. Dad is in really bad health. He could be any moment that, you know."
He embraced me. "I understand. Let's not talk about it right now. Let's eat. I'm starved. I ordered a lunch for us to be served right up here. I'm getting tired of some of those supposed upscale restaurants in New York. They seem to cater to business people trying to impress clients and the food is not consistently good."
What a great lunch we had. I won't describe it, I'm not a restaurant critic, but it was tasty and not too heavy. Wes said that one can't sex well on a full stomach.
We talk a walk around the gardens after lunch and then went back to his apartment. I have to tell you that Wes is the king of kissers. He's perfect, never anything to turn you off. He builds up until you are so drunk with feeling. That part of him was a terrific attraction. While sex may fade, kissing is forever.
Now let me tell you about the down side of dear, handsome, rich, supreme kisser Wes: he is way too fastidious to enjoy down and dirty sex. He doesn't give oral; likes to get it, but prefers wanking. While he is a dream to see naked, his equipment is less than modest. That doesn't really bother me, but it probably inhibits him. Now I like mutual masturbation or one party getting off, but it seems like kid's stuff and ought to proceed into deeper events. Then too, Wes is one of those fast comers, while I have learned how to last long and then explode.
In other words, we are a bit out of sync in timing and experience, but he's so loving and so beautiful, it almost makes up for it. Is that 'almost' a deal breaker?
Anyway, from the excitement of kissing, we undressed each other and enjoyed roaming around each other's bodies. We were in a high state of arousal and we reached for cocks and began stimulating each other. I could see that Wes's face was getting red and a faint odor of sexual sweat was apparent. That usually means that he was on the brink. He, for the first time, used his tongue as he kissed me passionately and groaned into my mouth as his cock began spitting huge loads of stuff on my pubic hair. He never stopped shagging me, but I had a way to go.
When he finished, he looked sad at me. "You didn't get off. I wish I could blow you, I just am not into it. Shall I continue wanking you?"
"No that's okay. I enjoyed making out with you. I don't have to come every time."
We had a nice time after that, listening to his prodigious music collection. We played squash and other jolly boyish things but finally I had to leave. I left the vacation thing open. He began kissing me goodbye, but I deftly moved back. It got me too hot, his passionate talent.
"I guess Wes won," that was Greg, waking up from a nap, clad in his undershorts. As I sat on the bed, I admired his excellent chest, so smooth and white with two cherry colored nipples. He also had a nice smell when you got this close. How can I describe it, a bit like a puppy who had just nursed.
I gave him a rough outline of the visit with Wes. His eyes opened wide when I described the little luncheon.
Finally, he asked, "What did you decide."
"Well, Ted is a hot, big boy, but his bossiness is sometimes off putting. You know I'm kind of an alpha myself."
"Do I know it and you need a little taming, maybe spanking." Had he been thinking of that. The idea was a little sexy and my peter thickened.
Now Billy is a fun guy, really funny, and he is outstanding as a bottom. He doesn't act like he's submitting, he glories in it. It makes me feel like I am a great lover, but he's never serious and I feel like I really don't know the real Billy."
"About fucking, I do both."
"Are you auditioning?"
"No, I'm just saying...oh forget it."
He was waiting for more about Wes, I don't like to gossip about other guy's sexual personalities but I did reveal Wes to Greg.
"That's not real meat. He might spoil you with material things but you'll feel like an old man's bought boi."
I sat there, oddly enjoying the closeness with my best friend. "I guess I'll skip vacationing with each of the three, but I hope they will still keep seeing me."
Greg sat up in bed and pulled his legs up almost to his chin. "You know, and it's costs me a lot to say this, but you have in your roommate a combination of all of those guys. The best is right in front of your nose, stupid1"
I stared at him. I felt a rush of recognition of ideas I have had fleetingly but never thought out. It is true that he is kinder than any other the others, not beautiful, but nerdy cute off the chart.
He watched me, his pretty lips puckered slightly. "Try me out."
I leaned forward and put my lips on his with only slight pressure, but it felt so good I pressed a little. My chest began rising and falling as I slipped into a great kiss. He possessed me with his lips. I had never had that happen before.
We parted, looking at each other in wonder. Suddenly he said, "What you need is to be fucked. I'm the guy to do it."
"Oh sure. I'll keep my manly cherry thank you, but that other thing you said."
"What, oh, yeah."
He put his feet down on the floor and pulled me over his nearly bare lap and pulled my elastic waist pants down along with my shorts and bared my ass. I was strangely passive, not my usual attitude.
"What we got here is a perfect ass, a dimpled ass, an ass with nice muscles, but it belongs to a bad boy, one who has ignored me for a full year."
His had a slim, well shaped hand, one usually busy on a computer, but now he splayed out his fingers and lifted his hand to shoulder height and let it stingingly slap my ass, right in the middle.
I grunted in discomfort, but when he asked, in a gruff voice I had never heard before, "You need more, don't you?"
Hearing my own voice say, "Yes," surprised me.
He started manhandling my body. I resisted, but he spoke strongly at me. "Bobby, you can't continue like a girl at the cotillion filling your dance card. That's not real life. You've protected yourself from really living."
"You really think so. I know it felt like something was missing."
"What was missing is real passion, real engagement. You've been holding on to your virginity, now it's become an obsession and you expect others to bend to you...to be perfect. Honey, give it up! Now!"
By the end of his rant, I was lying on my back. I grabbed his chin. "Greg, you think the answer is to allow myself to be fucked?"
"Absolutely."
I let out a deep breath I hadn't realized I was holding and slowly my legs lifted until I could reach them with my hands. I grabbed my ankles. This gesture was giving my ass to Greg."
He made a deep guttural cry and climbed between my legs. He said,"I guess you know that I have always loved you roomie, and I think you love me."
His cock head rubbed on my sphincter. While it felt strange, it felt like I had always know the feeling. I sighed as I felt myself opening to my lover. I suppressed any pride.
"Come in, I want you," I husked.
He slowly slid his prick into my yearning passage. I felt full. I felt happy. I pushed forward, empaling him completely. As he moved gently in and out, I felt an orgasm, a deep feminine flutter. I felt several of them as he fucked me, stopping occasionally to deep kiss me.
"It's time," he whispered and I rolled into a heavy ejaculation, spurts left my body over and over again, accompanied by cries of release. He joined me, pelting my insides with hot sperm. We clung together like two kids braving the storm.
When we could talk again, Greg said, "You will spend the summer vacation with me, at the Shore."
"Yes, Greg." There was no question in my mind. I had finally picked my BF.
End of story