tagFirst TimeTwo Bennington Blind Dates

Two Bennington Blind Dates


I was a "freshman counselor" overseeing and living with 12 Ezra Stiles College freshmen on Yale's Old Campus. I had a single room, free meals at the freshman dining hall, a good stipend, and money to spend as I saw fit to socialize my charges into college life. Combined with my full scholarship, I had no expenses and was living well.

For the last three years I had worked summers in the Governor's office in Harrisburg. Toward the end of last summer I was assigned to work with two staff people preparing a major gubernatorial announcement. Helping us was Martha, a fiercely loyal assistant secretary to the Governor. I met her daughter Sarah when she came into the office to meet her mother prior to their going somewhere after work.

Sarah was starting Bennington in the fall. She had a lively sense of humor, long brown hair, a decidedly feminist point of view, and a smile that would melt icebergs.

Early in October I was at a rowdy Branford College beer party when I ran into Sarah. "What's a nice girl like you doing in a place like this?" I asked, knowing that she would push back. "Dumb place. One of the girls in my dorm knows this guy and she brought me along. His roommate is really after me. I'm afraid of him."

"C'mon, we'll go over to Stiles. He'll never find you there."

We danced at that more sedate party and I introduced her to two of my charges, David and Chris, who she charmed. At the end of the evening we found her friend and she safely escaped New Haven.

David and Chris were agog.

"You know somebody at Bennington? Can we road-trip up there?" Bennington in those days was a Yalie's wet dream, an all-girls college where it was believed that boys were devoured by sexually omnivorous beauties.

I'd never been there but I said it was probably not quite like that. Nevertheless, because I liked Sarah, I called her and arranged to visit in two weeks. She thought she could arrange blind dates for David and Chris.

Sarah and her friends Margaret and Fran, who roomed together, met us in their common room around 6. Everyone clicked and we went to a folk music concert and a reception afterward. Sarah beamed like the successful matchmaker she was.

Around 11 I was ready to start the three-hour drive back to New Haven, but David and Chris hung back. Margaret said we could stay overnight if we didn't mind sneaking into her room. I looked quizzically to Sarah, who winked. I took that to mean that I was invited also.

We crawled through an unlocked window at the end of the hall and sprinted for Margaret's room. (Later we found out that this was a venerable Bennington tradition that posed no real risk of discovery.) The sleeping accommodations in their room were a set of bunk beds.

Fran soon had Chris with her on the edge of the top bunk while David, Margaret, Sarah, and I were sitting on the floor in the middle of the room. We passed a joint around and told silly stories in squeaky voices. Soon Chris and Fran disappeared from sight and Margaret motioned to David to move with her to the lower bunk.

Sarah's room was down the hall. Her roommate was already asleep. Did I want to go there or should she bring her mattress here, she asked.

"I'll help you with the mattress," I volunteered.

"No, I'll do it myself. You never know what these busybodies will do if they see you."

While Sarah went for her mattress, I listened as the whispering got quieter and quieter and the bunk beds began to squeak. When Sarah returned, we rearranged the desks in one corner and made ourselves a little nest.

"They'll be new men in the morning," Sarah said. "I've never seen couples join up this fast."

While the Bennington winter home uniform was jeans and a sweatshirt, Yale road dress was jackets and ties, shirts and slacks. I had shucked my jacket and tie while waiting for Sarah and now we took off our shoes and socks and slid under the blankets, the only bedclothes that Sarah had brought along. We faced each other and I reached for her. She met me halfway and we locked into an embrace the consequence of which was pretty clear.

My beard must have tickled and she pulled back. "Doesn't it itch?" she asked

"No, so long as I keep the neck shaved. I forget it's there most of the time."

We kissed some more and soon were unbuttoning each other's shirts and pulling them off. I reached for her bra but she was already there, releasing it to reveal two lovely melons. We played with each other's chests for a while, me kissing her breasts and she working my nipples and drawing pictures on my chest and belly hair with her finger.

"You really are hairy. I can't get over it."

"Roll on top of me and I'll share."

Instead she held herself over my chest and swished her breasts all over, then lay beside me and resumed running her fingers from my throat to my pants. She hesitated as she got to my belt.

"Are you okay with the fact that I'm a virgin, Pete?"

"Fine time to tell me, now that you've got me in bed," I said. "Yes, of course Sarah, I am fine with that."

"Okay then, let me take your drawers down," and she undid my belt, unzipped my fly, and had me arch my back so she could pull off my slacks and briefs and add them to the pile of clothes.

"You really are a hairy guy!"

"I've heard that a lot lately. May I check out your condition?"

She arched her back and I quickly had her jeans and panties on the clothes mound. We clasped again and I pulled her on top of me, because I love the feeling of a woman's bush against my cock. We kissed tumultuously, humping and grabbing. We were out of breath and came up for air.

"Sarah, you are beautiful. I've never been with someone like you. Your legs are strong, your bush is a perfect triangle, your hips are slim and feminine."

"That is such Yalie bullshit, Pete. My legs are too short, my feet came from different bins at the factory, and my bush needs tending. But I do like my hips."

All this was whispered because we didn't want to distract Margaret and Fran from ministering to David and Chris. We needn't have bothered, though, because at one point we heard David say "ooooooooh, Margaret, I'm cumming," followed by serious bed shaking. And when Fran's breathy voice came from the top bunk saying "Chris, stop holding back. I'm gonna make you cum!" we knew they weren't going to be distracted by anything we said or did.

The blankets were off as I worked on Sarah's belly. She squealed when I sucked her navel and then blew into it. By the time I inserted my finger into her opening she was wet and breathing heavily. As I played with her clit she began to swing her head from side to side and tensed her legs.

Any inclination I had to go slow disappeared and I lubricated my cock with my saliva and spread her legs enough to kneel between them. I estimated the angle and pushed, but I was low, so I pulled back. I was ready to try again when Sarah grabbed my cock and guided me straight into her.

"I want you now, Pete, all the way in, that's nice," she said, making sure everyone in the room could hear. Sure enough I was there. She didn't cry out but she did bite her lip.

Once she adjusted to my cock, we became very mobile. We caught our rhythm quickly and she didn't care who heard her. "Oh yes, oh yes, oh yes" as we crashed against each other. When I was ready to cum I whispered it in her ear. Her response was a loud "Fill me up, Pete, give me all your cum!"

We collapsed exhausted in each other's arms. As we regained our composure, I told Sarah how surprised I was at the turn of events. "I didn't expect this to happen. Chris and David thought Bennington was alive with sex but I told them not to expect any such thing. You've changed their lives."

"When I told Margaret and Fran about how you saved me from that Branford creep, they said 'you owe him big time.' So when you called I asked them to help me out, at least go to the concert with Chris and David. For all I knew they would dump your guys and you'd be on your way after the concert. I'm really glad they clicked."

We shifted positions as my cock got soft and began to slide out. "Ooooh, that's neat. And now there's the cum."

"Yes, it's not absorbed."

Since it was unwise for us guys to be in the hallway, Sarah found a fire bucket for us to pee in. The girls went to the bathroom down the hall, cleaned themselves up, and came back with wet towels for us.

So there we were, three ever so slightly stoned nude couples at 1 a.m. in a Bennington College dorm room, warm from sex and ready for more. Margaret broke the silence.

"I've got another joint. We can get real mellow. It makes the fucking so much better." She passed it around. I took a hit, then a second one. The taste was harsher than I could handle, so I stopped smoking.

The others took several really deep drags, and Margaret produced a second joint. The effect on the two guys was obvious and they got giggly. Sarah was more subdued and I couldn't tell about Margaret and Fran.

About ten minutes later Margaret said to Sarah, "You and Peter sounded like you were having fun."

"Almost as much fun as you guys did. This is a wonderful night, I never want it to end. Pete here looks like he's still my friend" as she took a playful poke at my reinvigorating cock, "so if you'll excuse us . . ."

"Have a blast. I'm gonna take David around the world myself," said Margaret, and she pulled David into her lower bunk. "Not me," said Chris. "I'm gonna get ready for Sunday school," at which point Fran whacked him on the shoulder. "Ow! That —" Chris started to say, but Fran clapped one hand over his mouth and grabbed his cock.

There was a wet spot and some blood on the mattress. We applied a towel and got back under the blanket. Where there had been haste before, now Sarah lay languid beside me as we kissed and fondled. My fingers traced around her clit, in and out of her opening, and back to her hyper-sensitive navel. She undertook a close-up inspection of my genitals.

"I've never been this close to male plumbing before," she said. "I would have thought it was all one piece, but it seems like it's pasted together." She spread the pre-cum around, then kissed the head. When I indicated my pleasure from this with a really deep moan, she started to stroke up and down with her whole hand.

"Wet your fingers, please Sarah, and make a circle with your thumb and forefinger. Dry friction starts to hurt after a while."

"Can I just suck it?"

"You've found my weakness. But I'll get randy, so let's not do this too long. I much prefer being inside of you."

"And that's where you're gonna be," she said, flipping me on top of her with as deft a motion as I've ever gotten from a girl.

"No, not this way," I said. "We've already done that. I want you on top of me."

"How's that work?" So I rolled onto my back and brought her up, straddling my hips.

"Slip my cock into your pussy. Work on the angle — oh, there, that's almost it. Now, now you've got it," I said as she settled her weight onto my hips and my cock deep into her. She winced but soon was comfortable.

"Now move any way that feels good. I'm yours, make me the agent of your pleasure, I'll just play with this" as I ran my thumb across her clit.

As her gyrations increased, I pushed my hips up and met her again and again. A small orgasm was followed by a bigger one. Sarah just bounced and bounced. When she came down from her big orgasm she said "I'm gonna die, I'm gonna die."

She recovered soon enough and said, "Now I'm gonna get you," and she worked her pussy against my cock. True to her word, she had me pushing my waves of cum into her within three minutes. We collapsed in each others arms and fell asleep quickly.

We had a lovely breakfast in the dining hall. There must have been a dozen guys besides us there and no one took any official notice. We got a guided tour of the campus, which is a very different world from Yale and the city of New Haven. By noon we were on our way.

"I want to apologize to you guys," I said. "I had no idea this was going to happen. I hope you won't tell the dean."

"You have our word on that," said David. "This was really amazing. It's like you had it all arranged and we just happened to show up."

"My duties absolutely do not include pimping," I said. I told them what Sarah had said, but my description didn't satisfy either of them. "We weren't here five hours before they had us to bed. It seems like it was arranged before we got there."

"Not me, guys. I like Sarah but I'm 24 and she's barely 18. We've never dated. I didn't expect any of this."

"Peter, did you know they switched around?" said Chris. "I woke up and there was Margaret sucking my cock. She covered my mouth and said 'shhhh, Chris, you and Fran were having so much fun I wanted some of you for myself.' "

"Yeah, it was strange," agreed David. "They are very different. Frankly," and I heard him blush from the back seat, "I liked Margaret more, maybe because she did a couple of amazing things to me the second time we did it." Chris agreed about Margaret, saying Fran seemed like she was enjoying herself but was only incidentally interested in him.

"Well guys, that's the wacky world of sex. You're already ahead of me on the curve of the number of girls in one night. Are you gonna see them again?"

"I don't know," said David. "You're the one with the car. Are you gonna go back to Bennington?"

"She's coming down for the Brown game," I said. "They run a bus to New Haven if there's enough interest, so there's your chance."

Sarah had said she didn't care for football, so I assumed that she was coming just to be with me. I got her a room in a private house just off campus, so that when she arrived at my room with her bag all we had to do was walk a couple of blocks to settle her in. But that was not what she had in mind.

"Pete, did David and Chris tell you what happened?"

"You mean Fran and Margaret? Yes."

"Anything else?"

"No. Was there something else?"

She hesitated. "Yes."

"Okay, tell me."

"I was with each of them."

I really liked Sarah. I had never been involved in a three-way. In fact, it turned me off. Still, that was up to them.

But Sarah's confession was a real jolt. It wasn't that she was so virginal in our fucking that I didn't think she hadn't fooled around. And I'd never asked any of the girls I'd slept with who, or how many, guys they'd been with. But this was different.

"Was this your idea?"

"No. And yes." She looked down at her lap. "Fran and Margaret are bi-sexual. They've been lovers ever since they arrived at Bennington. I turned down their offers to go to bed, because I've only thought about sex with boys.

"They said they'd double-date with us if I would agree that we all slept in their room. I wasn't sure about that, but I figured if David and Chris were okay, why not? I wanted to make love to you and as far as I was concerned they could do what they wanted.

"The weed in the second joints was spiked. You conked out pretty fast after we fucked, but the rest of us were rolling. Margaret was doing David really slow and she motioned me into the bunk. I was so high and so horny. I figured I'd just watch, maybe make occasional lewd comments.

"But Margaret wanted me to participate. She had a dildo and worked me in front of David, then told him to fuck me. He couldn't get it up so she had me suck him. He was semi-hard when I gave up and she just got on top of him and rode him until he came.

"Fran had been listening and she came down to take David over while Margaret and I went up to Chris. He was pretty out of it but he perked right up when Margaret pushed her pussy into his face. She had him lick her as I sucked him. When he came in my mouth I wasn't ready for it and I spit it out. Margaret shook me real hard and told me never to do that ever again. Then she and Chris set up doggy-style and she had him play with my tits and clit.

"The thing is, Peter, I loved it. You helped me get rid of my virginity in the way I wanted. Now I know I can fuck long and hard.

"I was going to just fuck your brains out this weekend, but I'm not going to. Margaret and Fran have this party going with some guys in the graduate dorm and I'm going to go with them. I just came here to explain everything and repay you for the room." She handed me a $20 bill and left.

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