Friendships and Sex

Friendships and Sex

Anonymous Robin

2019

I've known Penny and Jack since college. Actually, Penny and I were friends from the beginning of college whereas Jack showed up midway through senior year.

Penny was one of the critically honest and important friends. She was roommates with my first girlfriend during the formative transition from parents to independence. Having not dated much in high school, college dating was a steep learning curve. I fell hard in love and Penny kept me grounded and balanced. At least as well as any friend can. And she was there for the recovery after the inevitable breakup. She was also there for all of the subsequent breakups that predictably followed.

Jack eventually became just as important. It wasn't that either of them was any more experienced or wiser than the rest of us. But they just had a way of trying and learning from new experiences. They were just pure souls with humble self awareness.

After my recent breakup from Kim they were once again present and comforting. Kim and I were great; as were all of my relationships. Truthfully, I am a great boyfriend. I am attentive, present, and sincere. And generally a giving lover. Penny's analysis is that I am not doing anything wrong. Her theory is I just choose the wrong mates.

Her feedback stung a little more this time as she elaborated on the idea that I don't know myself. The premise was that my lack of self awareness won't sustain an evolving and changing relationship. "Dude," she quipped over breakfast. "You pick great girls. Like really, they are super. But I am not sure you ever ask yourself if they are who you really want to be with."

"But they are amazing. All of them. Kim, Jill, Kimberly before Jill... Most of our friends are always impressed with everyone I date." I replied.

"Yah, sure," Penny challenged. "But don't they all seem too similar? You could exchange any of them and start back at the exact same point."

I wasn't exactly sure her point. "That just shows you I know what I like." I was a bit defiant and wanted Penny to agree this was a strength.

"Maybe what I am saying is you know what others' find impressive. But what do you personally desire?"

I've always been proud of who I could sleep with. Most guys were in awe of my girlfriends. "I like who I date. What's so wrong with being selective? All that is lacking is a friendship like you and I have. That's what is missing."

"Really?, you think you are looking for our friendship? You've never seemed close to any of your girlfriends. They just seem so physical. Almost trophy like."

I must have looked puzzled as Jack arrived home from a run to hear where this conversation turned. "Another recovery. This sounds fun. Hey, I've got a question about friendship. Have you ever slept with any of your actual friends?"

Where the hell is Jack going with this? "I want to be friends with my girlfriends. It just doesn't progress that way. We always break up before it gets that comfortable."

"Then don't try to make girlfriends into friends. Why not allow friends to become girlfriends." Jack seemed to swoop into this conversation a bit late. "And on that topic, why didn't you and Penny ever hook up?"

"Yeah, why is that? Never even a drunken makeout between us?" Penny chided.

"Please, you and Jack were always together"

"Bullshit, you and Penny were friends years before I showed up. And you know that all through college we were never exclusive. Penny dated lots of guys even after I entered your scene." Jack started cooking breakfast by this point. Was Jack right? Penny and I were alone a lot. We traveled, went to parties, and flirted a fair amount. I never wanted to mess that up. Then when Jack started hanging out with us I was always the supportive friend.

Penny grabbed this concept, "Seriously, would you consider any of your girlfriends actually friends? Have you ever hit on any female friends?" I couldn't answer. I probably had a dumbfounded face while I scanned through history. "Shit man, there were times I was so obviously inviting you to make a move. And so many of our friends wanted you. And what did you constantly do? Brought some outsider beauty to our events only to absorb your attention."

Jack and Penny kept chiding me while touching each other. I think they were getting turned on talking about guys she dated in college. I couldn't even defend myself while they were having fun. My mental energy was scanning our past history. There was no lack of attraction towards Penny. I was constantly trying to get glances of her. We were together changing clothes, late night drunken games, even a skinny dip or two in groups. But damn it, she was right. I never expressed any interest in hooking up. I would hit on nearly anything pretty back then, but never Penny or anyone in our close circle; why?

Without any deep response from me the conversation shifted to other topics. We drank coffee for a while, talked about work. I left later but reflected on these thoughts most of the night.

The frustration of not having an answer continued for several days. Were they right that I never slept with anyone I considered a friend? Wasn't it wrong to sleep with friends? Where did that view come from? Was that related to me not becoming friends with girls I did date?

The thing about self awareness is it can turn positive or can go poorly. In this case it turned towards a life changing pleasure experience. Our next interaction as a group veered off the default path, like way off the beaten path.

The next few conversations kept returning to our shared pasts. Once Jack showed up Penny was no longer just one of many friends. Penny wasn't just a platonic friendship that stayed in the background. Jack was a fitness freak and Penny transitioned from a plump friend to a marathon running hottie. She could hold her own with any of my so-called trophy dates. I still didn't lust after Penny as our friendship was in a deep groove. Yes, I looked at her body as she transitioned. We were never the brother and sister type either, although I didn't object when people described our friendship as very close. I do remember several parties where we were definitely rubbing our bodies together on the dance floor.

Our absence of dating each other was mostly just timing. I was nabbing very exciting girls. Penny was gregarious. And once Jack arrived his presence made her even better. I would have stunted her.

These memories influenced the next several days until I found myself sitting on the couch with Penny between Jack and myself. Penny dressed in some light thin sundress magnifying her amazing athletic figure. I was hyper aware of her attractiveness now that I reconsidered our past. It became apparent at some point that we are all really close physically. Penny was leaning into my body at times.

Jack began giving Penny a foot massage which just pushed her body more into mine. At some point I turned slightly sideways so that I could give Penny more of a backrub. Penny closed her eyes to absorb herself with the attention. She had a peaceful smile which made her lips alluring.

"We can keep watching or continue this. I'm really enjoying the sensations." After a small pause Penny spoke her inner thoughts. "Oh, I should have mentioned, Jack and I talked and we'd be fine helping you cross the friend zone."

My mind didn't fully solve the riddle of that statement before me. Call me slow but we continued our joint rubbing without concern. Penny slid further down with her head down in my lap. I hoped not to get aroused but something was stirring. Jack's hands were freely moving up and down her calves. My hands stayed above her shoulders focusing on a head massage. My fingers slid through her shoulder length hair after I removed her ponytail.

Jack smiled when I looked up from gazing at Penny's body. His smile was clearly giving me permission to continue. Her breasts were lightly covered by the triangle of material of the sundress and I just wanted to look at them without freaking Jack out. Her athletic flat stomach was clearly present under the dress as the bottom hem flawlessly draped down midway of her thighs. Jack's massaging ever so gradually raising up her thighs.

"Not to disturb the mood, or to rush you through your breakup recovery, are you in a headspace for say, a new experience?" Penny's eyes opened and she stiffened slightly waiting for a response. I paused my massage but Penny didn't get up. She gave some internal thoughts before relaxing back into my lap. Jack and I restarted our massaging while my mind finally interpreted Penny's earlier statement.

"I say we just continue until someone wants to stop. Penny and I talked and are both interested in going as far as you want to." Jack seemed to want to assure me of their intent and interest. By now I was fully aware of what was available to me. I had the opportunity to share my best friend, sexually, with another close friend. If I had boundaries between sex and friendship they were being torn down.

Penny squirmed to guide our hands, her mischievous smile grew. A quiet chuckle from Jack lightened the atmosphere. In response to my slowing massage, Penny opened her eyes inquisitively. Her glare was evolving to arousal. "Are all friendships safe?" my voice cracked from dryness.

Jack was the last one to speak. "We are both excited about what could happen here. And yes, we both want our friendship to last a long time. Learn that friendship and sex don't need to be separated." Penny in full zen mode simply replied with an affirmative uh hum.

Jack smirked as he reached up and pulled one of Penny's dress straps down off her shoulder. The material lay uncontrolled across Penny's right breast. My hands continued moving along her neck but my gaze was solidly on her tits.

Jack reached up again and pulled the dress further down. Penny for her part rolled her arms until the dress jumped over the breast entirely. The flesh of the nipple was now completely free. I glanced at Jack for assurance. Penny reached up and pulled my hand onto her tit. A full body shutter followed. I was cupping an amazing tit, perfectly proportioned. Larger than my hand but firm enough to hold shape.

I swallowed and pulled the other strap down with my other hand. Both gorgeous breasts available to my discretion. Penny rolled to the side with an exhale sigh of comfort. My eyes fixated on her amazing body. Jack's hands past her thighs rubbing her ass as the dress was lifted up on her waist.

"A few rules," Penny lectured, opening her eyes and turning to me. "You have to promise this won't hurt our friendship. Jack and I both want this experience. We also want you to know friendship and sex can be intertwined, maybe should be intertwined. Also, we are all new to this. Everyone has veto power, Anyone can say stop and we all stop."

Jack and I both replied with affirmation. Penny closed her eyes, lowering her head down onto a fairly advanced erection. Jack silently pulled the dress down over her waist and off her feet while Penny sensuously lifted her hips to accommodate. Only wearing the most exciting panties, her bare body consumed my attention. I swallowed hard trying to pace the experience. Here is my longest best friend, my hands sliding through her hair down along her back. Her skin was smooth and sensual.

I massaged her tits while Jack's hands moved up her thigh grazing her pussy over her panties. As Jack's hands slide back down to her calves, my hands slide down her stomach onto her pussy. My hands lightly explored new areas, eventually sliding down into the panties. Her pussy was clearly trimmed and wet. Penny sighed expressing contentment.

Jack and I made eye contact long enough to commit to a plan. It was all about Penny as we choreograph our joint movements. I slid back up to her neck over her erect nipples. Jack moved back up to grab the panties and pulled them off. He returned to her pussy with penetrating fingers. Blood was visually filling the clit, further magnifying her sensations. My hands stretched her arms above her head, then slid along her full side down her waist. As my hands return upward I drew them onto her clit and press while Jack's fingers probe her inside.

As my hands return to her chest, Jack repositioned and went downtown, in what can only be expressed as a starving man finding food. His tongue explored all crevices. His mouth excompased her pussy in its entirety. Penny moaned in delight, brought her hands behind her head to directly touch my excited penis. As much as she could concentrate she began opening my pants totally by feel. She then reached up behind my head and pulled my head down to hers. My mouth reached hers and we kissed a kiss of desire. She breathed faster as Jack was doing his task well.

Penny rolled slightly to her side and finished opening my pants. I must have shifted my position to help as my pants were quickly down my legs. Penny opened her eyes for a close up of my excited cock. Normally I'd have some anxiety to be inspected so closely. Her hand grabbed and stroked me almost of the cadence of Jack's licking. Pre-cum dripping down to her fingers. Then she propped herself up and brought her mouth down onto my shaft.

We all slid off the couch and down to the floor. Penny in this move rolled from her back onto all fours, still blowing me. Jack undressed himself and positioned behind Penny ready for penetration. As he pulled her onto his cock, Penny raised up and started kissing me. Jack wasn't exactly pounding her but was giving her a pretty decent fuck. My eyes met Penny's while Jack was fucking her from behind. The contact was the most intimate connection of our long friendship. Penny regained her composure, started stroking me with both hands, while sticking her tongue completely down my throat. Her body couldn't hide the fact that she was cumming from what was probably her most intense sexual experience ever.

Jack indicated he couldn't continue much longer and needed to pull out for a break. Penny bit my ear lobe and whispered her intention to fuck me. She asked if I wanted to fuck her and wanted to know if this was OK. Some of her words were too quiet to comprehend but something about being so happy that we could share this.

My answer was to lift her onto my legs so she was facing me in a sitting position. I was playing with her tits while she kept stroking me. With a glance back to Jack for affirmation, she hopped up and dropped onto my stiff erection. Her hand still on my cock guided me into her still excited pussy. I was on the floor leaning against the couch while she was humping and kissing me. Jack got up and sat next to us on the couch allowing Penny to give him a strong hand job. Penny was able to coordinate alternating between kissing me and blowing Jack. I wasn't even freaked out with Jack's erection right next to my face. Penny was bouncing up and down my shaft while I was eye to eye with Jack's cock shoved down her throat.

I was soon near my end and definitely didn't want to cum inside her so I pulled her off of me. Penny pulled us both down to the floor so she could blow or give both of us handjobs. While she knelt between us, we both had our fingers deep up her pussy. One of us kept attention on her clit giving her another long orgasm. While her body stiffened, her hands squeezed our erections just slightly too strong. This final move and sight was all I needed as I came hard with my cum covering her hands and my stomach. That was probably all Jack could take too as he also came shortly after, our hands still pressing up Penny's body. Both of her hands were covered in cum as she fell backwards leaning against the couch in ecstasy.

One of the most surprising outcomes from this experience was that our friendships hardly changed. We three continued to hang out with the same friend feelings as before. We have since replicated that threesome experience a few more times, always when it was natural and comfortable. Yet it wasn't the central part of our lives together.

I have also learned to date differently. I still largely choose the same type of women, but I enter relationships with just a bit better expectations. And maybe, just maybe, I told Jack he may get a reciprocal experience when I find someone just as open as Penny.