‘Friends with benefits’ conjures up various possibilities. Former lovers for whom the romance has faded, but the physical attraction remains. Acquaintances drawn together solely by lust. Perhaps two lonely souls, finding solace in the warmth of another’s body while they await the arrival of their soul mate. Or something else.
Which brings me to my story, of Sarah and me. I’m your typical sophomore guy in college. Sarah was my neighbor from where we grew up, she lived three houses down from me. We went to the same schools, although she was one year behind. Now, Sarah is a nice girl, but no beauty — skinny, with small breasts and a bony build. With a face people usually called plain. We were friendly growing up, although more neighbors than friends. She traveled in her circle, and I in mine. But we ended up going away to the same college, where she was a freshman.
It’s natural that people from the same town bond together when away at school. I’d see Sarah occasionally over a Coca-Cola, and we’d chat amicably enough about college and stuff. On this particular day, when we met, Sara was clearly glum.
“You are not your normal cheerful self,” I observed. “Are you ok?”
She didn’t respond immediately. Her silence gave me concern.
“If you’re in trouble, I’ll try to help. I won’t tell your parents,” I volunteered.
“It’s not like that,” she said.
More silence.
I let her take her time. Whatever it was, she’d have to want to reveal it.
“I’m a virgin,” she said finally, in a low voice.
“That’s not a problem,” I said. “Congrats to you for waiting for the right guy.”
“No, it’s a problem. I didn’t date much in high school, and the few guys who showed an interest, I never let go too far. But now I’m in college and I’m the only girl in my sorority who is a virgin. I’m a freak.”
“Don’t take this the wrong way,” I offered, “but there are lots of guys who’d be happy to resolve that issue for you.”
“I’m sure, but I’m not going to hurl myself at just anyone. I have some pride.”
“Shouldn’t you just wait for a guy you like a lot? And let things happen naturally,” I suggested.
She shook her head. “My worry is that I don’t know how to please a man. I’m afraid if I meet Mr. Right, I’ll chase him away when he sees how clumsy and dorky I am.”
She went on. “That’s why I thought of you.”
Huh?
“You’re a decent guy, and we’re friends. You could teach me. There’d be no obligation, I wouldn’t expect flowers or dinners.”
I was in shock. I looked at her. Small breasts, not pretty. Not someone I’d think to date.
“I’m sure that would be a mistake. You’d hate me afterwards,” I said. I was thinking fast, trying to get out of this situation.
“No, it wouldn’t be like that. I’d always appreciate you helping me. We wouldn’t have to tell anyone. I don’t have anyone else to ask,” she said, and I almost thought she was on the verge of tears.
Oh my God. “I can’t do it,” I said.
“Please. I’ve never been at ease with guys. In truth, they frighten me. I need to get over this hurdle. Won’t you help me?”
Now there was a tear forming in her eye. “I’ve made a fool of myself,” she said.
“No, no, not at all.” I was on the verge of panic. Could I tell her the truth?
She looked so miserable, I couldn’t just reject her. I had to reveal my own secret.
“I can’t teach you because I’m a virgin too,” I said.
“What?
I couldn’t look at her; I was so embarrassed. Here I was, twenty years old, and I’ve always been as clumsy and awkward with women as she was with men. It’s ok for a girl to be a virgin (it’s even celebrated), but not so for a guy. It’s the mark of a failure, one who has struck out with every woman he’s met.
“That’s perfect,” she said.
“What?”
“We can learn together. Neither one of us has to be ashamed of our ignorance,” she said. “I can help you too.”
“This is crazy,” I said. “So, we’d just meet and have sex? How would we even know if we’re doing it right?”
“We can watch sex tapes together, and do what they do,” she said.
“Sarah, I don’t know. This is crazy.”
“I know I don’t have big breasts, but I’m told I have a great ass,” she said, again with that tear forming in her eye.
I felt terrible that she had the need to ‘sell’ herself. What kind of guy turns down a woman offering her body? Was I a horrible person?
“Well, maybe,” I said.
“Oh, thank you!” she gushed. “I think we can do it this weekend. The sorority house offers zero privacy, but I have a girl friend who lives in town who’ll be away this weekend. We can use her place.”
She had it all planned out. Oh my God. Did I agree to this?
“I’m not on the pill, so you’ll need condoms. Do you have any? I can bring some; the sorority house has a supply.” She was in full flight now. I half expected her to discuss what kind of lingerie she’d wear.
“Shouldn’t we think about this a little?” I ventured. “So soon, this weekend?”
“Yes, this weekend is perfect. I don’t have any tests or papers due next week, and I’m just finishing my cycle so I won’t be fertile then. But we’ll use condoms to be sure.”
My mouth was hanging open. We’re already discussing her cycle? Are we a couple?
She smiled at me sweetly. “I’m really excited. Aren’t you?”
“Sure,” I replied. But in truth, while I’ve dreamed of having sex, now that it was being dangled in front of me, I was scared. Old fashioned performance anxiety?
Sometime days drag along. Other times, they whiz past. This was the latter. I had told myself I’d search the internet for tips, but I had papers due, and my damn roommate never left the room. I couldn’t very well review sex instruction tapes without provoking an interrogation from him; he was the nosy type anyway.
Two days later, on Saturday evening, we were together in her friend’s in-town apartment.
Sarah was dolled up, with a lot of make-up, a tight-fitting blouse and a short skirt. Her idea of seductive. It was sweet she made that effort. I felt like an idiot as I wore my usual blue jeans and a mostly clean t-shirt.
“Let’s talk about what we should do first,’ she said. “Do you want to take off my clothes? Or should I do it? Maybe we should do it together? Should we turn off the lights first? I brought some sexy lingerie. Did you bring sexy pajamas?”
Oh my God. I had to slow this down.
“We’re supposed to take this slow. Like, build some sexual tension,” I said. (Me, the expert.)
“Okay, why don’t you rub my back,” she suggested.
Good idea. I should have thought of that. She sat next to me on the couch and turned her back to me. I began massaging her shoulders and back through the blouse. I moved my hands to her front and cupped her breasts.
She unbuttoned the blouse. I pulled it off her shoulders. I unhooked her bra from the back and it fell away.
“I don’t have big breasts,” she acknowledged … again.
Her breasts were, indeed, small — just little protrusions. A well- conditioned male swimmer would have a bigger chest.
“They’re beautiful,” I said, although my heart wasn’t in it. But I’m sure that’s what a guy is supposed to say.
With her topless, it was time to play a video that I’d loaded onto my IPad at the last minute. We sat together and watched a fellow delivering pizza to an apartment of three attractive girls. The girls had enough money to pay for the pies, but nothing extra for a tip. You can guess how they decided to tip the delivery boy.
They swarmed him, pulling his clothes off while they shed their own. Soon he was sucking on the breasts of one girl, while another girl was sucking away at his penis which had risen mightily into the air.
Meanwhile back here on planet Earth, I had no such similar reaction to seeing Sarah’s small bare breasts.
“Why aren’t you hard yet?” she asked, in all innocence, staring at my undisturbed trousers.
“I don’t know. This is so strange,” I said. “I’m more nervous than aroused.”
“Well, I guess I should do what the girl in the film is doing,” she said. She pushed me down onto the couch and unbuckled my belt. Loosening the pants and undoing the zipper, she lowered the pants to below my buttocks. My male parts, in acknowledgment of her ministrations, stirred inside the underpants.
“That’s better,” she said. “Shall I suck on it?”
“I guess. Just be careful with your teeth.”
I was a little nervous about the teeth; I saw a horror movie once, where … (but no need to relive that nightmare).
She reached in and pulled my penis through the fly of my underwear, which helped it rise even more. She put just the tip of it into her mouth – then spit it out like a tourist in Mexico encountering his first jalapeno.
“Ugh, that’s weird. I just remembered you pee from that thing,” she said.
“You’re supposed to suck on it, not spit it out,” I remonstrated with her.
“Don’t criticize me,” she said, with a pout, like a scolded child. I feared another tear would appear.
“No, no, I’m just offering constructive advice. Remember, we’re here to learn.“
That comforted her somewhat, and she returned the penis to her mouth. With little, tentative motions, she moved her mouth back and forth. It wasn’t unpleasant, but I didn’t have the reaction of the pizza delivery boy, who was still thrashing about on the iPad from his encounter.
“Tell you what, why don’t we take a shower together?” I suggested.
That would resolve the clothes issue and maybe some soap on my genitals would encourage the penis to be more engaged. (It was used to excitement in the shower, albeit from my own hand).
“Oh, that’s a good idea,” Sarah said, perking up. I think she was mainly happy to get that thing out of her mouth.
We walked into the bathroom, and shed our clothes. We stood awkwardly together, naked, waiting for the shower water to get hot. That damn apartment building was old and the water heater must have been 19th century. We stood there for a long time, waiting, somehow not looking at each other’s naked body, although we were within twent-four inches of each other. Finally, it was hot enough and we got into the small shower.
I soaped her back first, then moved around to her front. Then down to her stomach. Then lower. This was working well and she made appreciative little moans.
“Your turn,” she said, and filled her hand with soap. She rubbed my chest muscles slowly and nicely, causing the penis to stir. She touched the penis briefly, then moved to my back.
“No, no,” I insisted, “it needs to be cleaned very thoroughly.” I moved her hand back to the penis. “And the testicles, too, they’re sweaty from a long day.”
Her first lesson in pleasing a man: don’t short change the male genitals.
“Is this what you like?” she asked with a smile, as she massaged my testicles. Her smile was a sweet smile that lit up her face, and made me realize that we hadn’t smiled at each other this evening. It was like a business meeting. That had to change.
“Yes, that’s wonderful,” I offered.
After a while, I asked her what she would like. She demurred, “Everything you’re doing is good,” she said.
Still shy with men, I thought. That too needed to change.
We got out of the shower and used towels to dry each other off. The gentle pressure of the towels excited the skin, and this also gave us time to study each other’s body. Neither of us had ever seen a member of the opposite sex up close like this before. Not just naked, but fully exposed to view and touch. I loved that her vulva was covered with a tangle of pubic hair, almost hiding the lips of the vagina. I parted the hair to look inside and rubbed gently with my finger. She cupped my testicles in her hand, moving them around like marbles in a sack. She was curious about my penis (“what’s it feel like when it expands?”) and commented on the ridge at the top. She knew enough to see that I was circumcised, and asked me about it.
When we were dry, we moved back into the bedroom and lay on the bed. I wanted to lighten the mood, get her back to smiling. “So where are you ticklish?” I asked, as I gently brushed my hands under her arm pits, on her rib cage, searching for a spot. She began to giggle when I found the side of her neck. I entertained her, blowing softly on the ticklish area, while gently massaging her breasts.
“And what about you?” she said. I told her about the soles of my feet – my secret weakness.
She turned and sat straddling my thighs, her back to me and leaned forward to massage the feet. I enjoyed the view of her bare back, and the curve of her behind as it rose when she leaned forward. She does have a great ass.
After a few minutes, she turned around to face me. “Shouldn’t we have sex?”
It was time. She stretched out on top of me. I put on a condom and positioned my erect penis against her vagina. I tried to thrust up into her, but this girl-on-top position isn’t for beginners. I couldn’t penetrate more than an inch. She didn’t know to thrust down (and I didn’t know to tell her).
“Let me be on top,” I said, and we rolled over as a unit. With me on top, entering her was much easier. But she was very tight, and I couldn’t get very deep into her. She grimaced; this wasn’t pleasurable for her.
“Are you okay?,” I asked.
“I don’t know,” she said, “it’s not very good. You don’t fit.”
“Are you wet?,” I asked. (I had read enough to know girls are supposed to get wet.)
“I don’t think so,” she said. “How wet am I supposed to be?”
“Let me use my tongue.”
I slid down to position my tongue over her vulva. I began to lick it but I was as skilled at this as she was at fellatio.
“You need to lick the clitoris, I think,” she said.
“Where is that?”
“It’s here,” she pointed.
After a little practice and with some enthusiasm, I was able to excite her.
“I think I’m ready now,” she volunteered.
I aimed my penis at her again, and this time I was able to enter a good distance. I rocked back and forth. I didn’t last very long and soon erupted with my ejaculation.
I lay spent on top of her.
“Was it good for you?” I asked her.
“It was fine,” she graciously replied. I knew I had come too soon. But once my penis found the promised land, it was not to be denied.
“It will be better the next time,” she said.
Next time? It hadn’t occurred to me that this would be a continuing occurrence, not a one-time.
“Yes, it will be. It’s good that we’re learning each other’s bodies,” I ventured.
We lay cuddled together for some time, feeling the warmth of our bodies. When I had recovered, I told her I wanted to enter her again. This time I lasted much longer, and her cute little whimpering sounds told me it was good for her too.
After a while, as we lay in each other’s arms, she dozed off. I watched her face as it softened with the caress of sleep. I was wrong to call it a plain face. It was an interesting face, maybe you’d say it had its own beauty. And those little breasts were well shaped and cute. Then I allowed myself to sleep too.
When I awoke, she was staring at me. Her hand was on my penis. Not stroking it, not using it sexually. Just holding it, as one might hold another person’s hand.
“Good morning,” she said and smiled that sweet smile of hers.
“Hi,” I said. When I looked down at her grasping my male organ, she laughed.
“Sorry, I’m still trying to get used to guys. And I find this a pretty strange appendage, changing size as it does. In the morning, it’s so small and vulnerable. Nothing like the fierce predator of last night.”
“Would you like to see it change shape again?” I asked.
“Why, yes, I think that would be lovely. After all, we need to see if I’ve learned my lesson from last night. You’re a very good instructor, but practice makes perfect.”
With that, she began to massage the genitals, stroking along the shaft, reaching down to the testicles. She was a very apt student. And we had sex once again.
We had many more sessions together. I thought we might become a real couple, but after a time, she met someone else and was smitten. She stopped our sessions, saying she and the boy had agreed to be faithful to each other. She told me very sweetly how much she appreciated what I had done for her. I felt the loss of our intimate time together more than I had expected. However, I never begrudged her her new boyfriend. After all, facilitating that was what our time together had been for. But we had the special bond that we were each other’s ‘first.’ Now the very best of friends, although without benefits.