I have always been friends with Ann.
We grew up together and dated occasionally. I wanted more from her, but it wasn’t meant to be. She was a good Catholic girl, and I respected the boundaries she had always set up. We “made out” more than a couple of times, but the furthest I ever got with her was groping her fleshy breasts with a bra and a blouse between us before she stopped me. After high school, we slowly drifted away from each other, but I always compared whoever I was dating with her.
After I finished school and started full-time work, I had a few relationships, but nothing that ever fully took Ann out of my head. She was parked in the back of my mind.
I was wondering what I might do for the upcoming weekend when, out of the blue, I received a message from her. We hadn’t seen each other in several years, and she had contacted my mother and left a phone number and a message asking me to call her.
I was ecstatic to hear from her. I wanted to know what she was doing, where she lived, and all the details of her life. I hoped she was unattached. I called the number she had left and only talked long enough to plan a get-together for a few days beginning Friday, two days away.
I was in for the surprise of my life.
We arranged to meet in Philadelphia since it seemed like a central meeting point. She had been living in upstate New York, and I lived and worked in Baltimore. An old college roommate, who was traveling in Europe, had given me access to his brownstone, and we agreed to meet there.
I arrived at his home and was pleased to see it was neat, clean, and orderly. I stopped at a nearby bodega and stocked the refrigerator and pantry with food and a few bottles of wine. I was so distracted by the thought of seeing Ann that I used vacation time to have a few days to get ready for what I hoped might be the first of more time with her.
I was as nervous as the first time we had dated as awkward teenagers.
I heard a knock at the door, and when I opened it, I saw Ann for the first time in years. She was more beautiful than I remembered.
She was dressed simply in a white blouse, black skirt, and comfortable penny loafers. She wore no makeup, and her hands were not adorned with a manicure beyond neatly trimmed nails. Her hair, which was always long and lush, was cut short.
She still could have graced the cover of any fashion magazine.
She smiled when she saw me, and I felt a sadness, regret radiating from her body. We hugged each other tightly, and we kissed. It felt awesome and clumsy and natural all at the same time. Her body seemed to perfectly contort against me, like puzzle pieces finally being joined together.
I carried her simple suitcase into the brownstone, and she asked me a million questions about what I was doing and how I had been. She basically caught up on me.
Then it was my turn.
The story she told me hit me between the eyes like a baseball bat.
After leaving high school and our hometown, she attended college for a few years. She dated occasionally and had been the victim of an attempted assault that was stopped when her roommate and her boyfriend returned to their apartment before the incident escalated. The perpetrator had been arrested and jailed. Eventually, he had been charged, convicted, and died in jail at the hands of other inmates.
I realized that if the man who assaulted her were still alive, I would kill him.
The emotional trauma had guided Ann to intensify her religious life. She left school and entered a convent. After spending a year in the nunnery, she prepared herself to become a nun.
She told me she had taken temporary vows and was now in a transitional period before making a final decision. Before deciding, she said she wanted to see me.
I was speechless.
“Tell me,” Ann said. “Tell me what you’re thinking.”
I couldn’t speak. I was overwhelmed by seeing her, hearing her story, and now sorting through what was spinning in my mind. I realized I wanted her as I had when we were younger. But how could I ask that? How could I compare to the Catholic Church?
“You need to talk to me,” she said. “I want to hear what you think.”
I stood up and took Ann’s hands and pulled her up. I pulled her into my body and leaned down and kissed her. Our mouths melted into each other’s, and her tongue pushed into my mouth. I felt the press of her breasts against me, and my cock grew and pushed against her crotch.
I was afraid I was too forward and might be rebuffed. If Ann wanted me to stop, I would respect her choice. But I had to try. I wanted to take her and let her body decide our next steps.
“Oh, God,” she moaned. “I have—I have to stop.”
I released my tight hold on her, but we were still holding on to each other.
We kissed again and broke apart.
We silently made dinner, and I opened a bottle of wine. We ate, each had a glass of wine, and then we cleaned up the kitchen together. The silence was not forced or uncomfortable, but I was at a loss for words or what to do next.
Ann looked at me and said, “I’m tired. I’m going to bed, okay? I’ll see you in the morning.” She approached me and gave me a deep kiss. Was this the last time?
I hadn’t told Ann what I was thinking because my head felt like a current of thoughts was raging through it like a river at flood stage.
I didn’t know what to do, so after she had closed the door to her bedroom, I showered and got ready for what I knew would be a sleepless night.
I drifted off to sleep.
At 2:00 a.m., I felt the sheets of my bed pulled back, and I realized Ann had slipped into bed with me. At first, I thought I was dreaming. Then I could feel the silky smooth touch of her against me. I had gone to bed nude and felt Ann’s nakedness next to me. I wanted to taste and lick and fondle and fuck her.

Ann said, “Hold me.”
She turned her back to me, and I spooned her. My engorged cock was nestled in the crack between her buttocks and throbbed with each of my heartbeats. She lay across my left arm, my right arm crossed and rested against her fleshy breasts. I could feel that her nipples had blossomed and stood out at least half an inch. My heart was beating like a jackhammer.
I felt Ann scoot tightly against me, and she said, “Sleep. Sweet dreams.”
After a few minutes, she was breathing rhythmically as she fell asleep. I thought it was the best and most difficult thing I had ever experienced. I knew I couldn’t sleep. She stirred and lifted her leg, and my pole slipped between her legs. Then her leg clamped down, and my cock was caught tightly. The tip of my dick now rested at the entrance of her sex as I strained not to move. I felt heat radiating from her. I was trapped in a situation I couldn’t fully comprehend.
But I did fall asleep and was awakened by sunlight shining on my face. Ann was gone. I still had a raging hard-on that needed release. Instead, I emptied my bladder and took a cold shower.
I dressed and found Ann in the kitchen making coffee. She had a light, silky housecoat on that wrapped around her body.
She smiled and said, “Good morning. Did you sleep?”
“Not really. I was distracted. We do need to talk. I’m ready to tell you what I think.”
“Okay,” Ann said.
“I would like you to experience me. You haven’t taken final vows and are in the world right now, with me. Can we let nature take its path? Whatever we’re doing, I’ll stop the moment you tell me to stop.”
“I will try, but I don’t know if I can,” she said.
“That’s all I’m asking. We’ll take it slowly. No rush. We’ll enjoy the day and see where we are. Okay?”
“Okay,” Ann said.
The whole time we had talked, we had our arms wrapped around each other. We ate breakfast, and I cleaned the kitchen while she got ready for the day.
She stepped out of the bedroom she was using and was dressed much like she had been the day before, wearing a simple black sweater and jeans with her loafers.
She looked fantastic.
We wandered around Philadelphia and went to the Art Museum. We took selfies with Rocky and ate a late lunch of cheesesteak sandwiches with Cheese Whiz. I know, it sounds disgusting, but it was awesome.
We got back to the brownstone in the early evening and opened a bottle of wine and ate cheese and crackers and smoked salmon.
As it neared bedtime, I kissed Ann and went to my bedroom and cleaned up by taking a quick shower. I didn’t know what would happen and, as much as I wanted to press, I backed away from trying to impose what I wanted with Ann.
Like the night before, I drifted off to sleep.
Like the night before, Ann slipped into bed with me. I thought I was dreaming as I felt her sidle up against me. I awoke and looked at her in the dark. I leaned into her and kissed her. Her lips parted, and her tongue made its way into my mouth.
My cock ballooned up, and my right hand cupped her breasts, and I pinched her nipples, one then the other. Her breathing was heavy, and a moan escaped her lips. I rolled on top of her and slid down to suck her breasts. I had dreamed of this moment and licked her nipples before sucking them gently and then with more force.
Ann squirmed beneath me but didn’t stop me. I kept kissing her as I moved down her body. I could feel heat radiating from her sex, and I smelled a sweet, musky odor.
Ann opened her legs, and I kissed the inside of her thighs. I discovered she had a bushy crotch of silky hair that hadn’t been trimmed. Beads of moisture glistened in the dark, and I tasted her. I probed with my tongue and found her slit and kissed her labia, her pussy lips, like I was kissing her mouth. I bit her clit gently, and she bucked involuntarily upward. I stopped momentarily and felt her hands guide me back to her cunt, and I kissed and slurped and pushed my tongue deep into her pussy as I felt an orgasm wash over her body. She shook and cried out, “Oh, my God! Don’t stop! Don’t stop!”
I kept using my tongue until I couldn’t. I could feel her release, and then she relaxed. I moved up her body and kissed her so she could taste herself. At the same time, my rock-hard cock was positioned against her slit. She raised up, and I pushed.
The head of my cock was enveloped inside Ann, and I felt a resistance. I backed off and could feel her raising up, and I pushed again and felt my cock gripped by a tight velvet glove. Every contour of my cock was as if in a vise.
Ann groaned, and I stopped. But I quickly started stroking as Ann rocked me by raising her hips.
“This feels too good,” Ann said.
I knew I couldn’t last. I felt a boiling sensation starting from the bottom of my feet to the top of my head. I started pulling out my cock until only the mushroom helmet of my dick remained in her, and then I pushed in until my seven inches bottomed out in her.
We were now fucking at an animal’s pace, and she started screaming unintelligibly, and I roared, “I’m cumming!!!” I erupted into her, dumping my pent-up sperm into her heretofore virgin body. Sweat streamed down my body and mixed with her sweat. I collapsed on Ann and struggled to breathe.
After a few minutes, we were both staring at the ceiling.
Ann looked over at me and said, “Can we do that again?”
When the weekend ended, Ann went home with me.
